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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

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With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

snowy new england scene frozen trees and pond

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

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Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

winter road trips in new england

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

road trip in new england map 4 day itinerary

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

  • Fenway Park
  • The Freedom Trail
  • Acorn Street
  • Trinity Church
  • Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

  • Southend for an authentic Bostonian experience
  • Cambridge for Harvard and MIT
  • East Boston for good food and views
  • Walden Pond for transcendental fans
  • Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

  • Lighthouses
  • Charming settlements
  • Trinket shopping
  • Historical landmarks
  • Biking and hiking
  • Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

cape cod sandy beach and ocean

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

road trip in new england map 7 day itinerary

7 Days: New England’s Best Fall Foliage

  • Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
  • Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
  • Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
  • Spend the night in Kent, Cromwell or elsewhere.
  • Admire the foliage.
  • Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
  • Arrive at the junction between I-7 and Highway 2 near Williamstown.
  • Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
  • Stay nearby and drive along the 2 to your heart’s desire.
  • Drive on the Mohawk Trail if you haven’t already.
  • When ready, head for Green Mountain National Forest of Vermont via I-7 again.
  • Drive through the Green Mountains until Burlington.
  • Grab a beer and chill for the night.

Today is a long but rewarding day.

  • Depart from Burlington and head for Cambridge, VT.
  • Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
  • Make your way east towards Bath, New Hampshire.
  • Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
  • Continue onto Lincoln, admiring the scenery along the way.
  • Stay in Lincoln, North Conway or elsewhere in the White Mountains.
  • Finish the Kancamagus Highway (112), which terminates at Conway.
  • Head north upon reaching Conway on Highway 16.
  • Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
  • Turn onto I-2 and then again onto 113 to reach Evans Notch.
  • Finish up and head south towards Portland for the night.
  • Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
  • Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
  • Spend the night around Acadia or back in Portland.
  • Consider spending the night in Camden as there is excellent foliage here.
  • Pack up and head back to Boston.
  • Spend the day exploring the city.
  • Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

map of new england road trip 14 day itinerary

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

  • Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
  • Explore the city and its architecture.
  • Be sure to drop by one of the many breweries and brewpubs.
  • Spend the night in or around Providence.
  • Wake up and head directly for Newport via Highway 114.
  • Spend the day exploring the opulent town.
  • Be sure to visit the many mansions and estates as well as Fort Adams in the south.
  • Depart when you’re ready.
  • Drop by Narragansett for some beach time if you have time.
  • Stop in Old Saybrook for the night or continue onto New Haven.
  • Depart from your lodge and make your way north.
  • Head to the state capital Hartford.
  • Wadsworth Falls
  • Buttermilk Falls
  • Settle in Hartford for some culture and good partying or…
  • Head to Litchfield Hills for a quieter night.
  • Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
  • Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
  • Hit highway 7 and make the long drive to Burlington.
  • Reward your hard work today with a beer.
  • Spend the day exploring the Green Mountains of Vermont.
  • Climbing the  Camel’s Hump .
  • Hiking around  Mt Mansfield .
  • Check out  Smuggler’s Notch .
  • Rafting on the  Mad River .
  • Spend the night in Burlington again.
  • Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
  • Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
  • Spend the remainder of the day in the mountains.
  • Flume Gorge
  • Mt Washington
  • Franconia Notch
  • Arethusa Falls
  • Lonesome Lake
  • If you arrived early enough, considering overnighting in a backcountry campsite.
  • Wake up and knock off any remaining activities.
  • Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
  • Lay your head down for the night, preferably around a campfire with a drink.
  • Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
  • If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
  • Spend the day exploring Acadia National Park.
  • Taking a road trip around  Mt Desert Island .
  • Climbing  Cadillac Mountain .
  • Visiting  Jordan Pond .
  • Relaxing on  Sand Beach .
  • Walking around  Bar Harbor .
  • Head to your lodge for the night.

fresh caught lobster from maine

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

boston skyline from the bay new england road trip

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

cap cod beach and fences romantic new england coast road trip

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

marble house newport rhode island

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

yale university new haven coast new england road trip

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

winter road trips in new england

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

an assortment of orange and red trees as seen from above on an autumn hike in connecticut new england usa

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

vermont snowy geen mountains new england road trip

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

white mountains of new hampshire new england

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

rugged maine coastline and lighthouse

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

great north woods new hampshire new england road trip route

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

mit docks and boston skyline new england road trip roaming ralph

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

maine coastline at dawn rocky and rugged

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

cows grazing in connecticut new england under fall trees

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

fall foliage drive in new england

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

winter road trips in new england

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

woman taking photo with new england foliage

Updated February 2023 by Samantha Shea

winter road trips in new england

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Ralph Cope

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New England With Love

The Flexible New England Road Trip Itinerary You Need in 2024 ❤️

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

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Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

A street view in Boston, capturing the essence of a New England road trip itinerary, with cobblestone streets and historic brownstone buildings, featuring distinctive green bay windows. The scene is set against a backdrop of modern skyscrapers, merging the old with the new in this iconic cityscape.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

  • Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
  • Stroll around quaint Beacon Hill
  • Tempt your taste buds with a Boston Food Tour
  • Go shopping on classy Newbury Street
  • Follow the Freedom Trail to learn Boston’s revolutionary history
  • Join an expert-led walking tour for a more in-depth experience of the city
  • Check out one of the many great Boston museums, including the Museum of Science which I especially love
  • Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

amy standing in a black fur coat in front of a shop with a sign that says Coffee Grinder

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

  • Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
  • Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
  • Stroll along the scenic Cliff Walk
  • Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

two white adirondack chairs face a calm river in mystic CT

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

  • Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
  • Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
  • See the adorable beluga whales at Mystic Aquarium
  • Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

A red covered bridge over a river with fall foliage in front

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

  • Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
  • Grab ice cream from Arethusa Farm
  • Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
  • Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Drone view of a highway through a forest of colorful fall trees

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

  • Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
  • Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
  • Take a hike on one of the area’s many scenic trails
  • Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
  • If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

A soldier's monument stands tall amidst the fiery red and orange leaves of autumn in the Northeast, with a clear blue sky above and a backdrop of a mountain. This image captures the vibrant fall colors, ideal for a Northeast road trip to see the season's change

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

  • Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
  • Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
  • In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
  • Shop til you drop at Manchester’s many outlet stores
  • Dine at the stately Ye Olde Tavern
  • Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

an image of an empty shopping street on a sunny day. colorful banners cross over the blue sky and a long bricked walkway leads to a distant church - burlington vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

  • Sail on Lake Champlain on the Spirit of Ethan Allen cruise
  • Walk down Church Street for shopping, eats, people-watching, and more
  • Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

A vibrant 'Welcome to Stowe, Vermont' mural painted on the side of a classic blue New England building, complete with hanging flower baskets. This colorful greeting sets the tone for a picturesque stop on a road trip through New England.

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

  • Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
  • Shop the adorable shops on Main Street
  • Visit a haunted covered bridge if you dare (Emily’s Bridge)
  • Spend a day skiing on one of the area’s fantastic ski mountains
  • One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

A serene lake reflects the vivid autumn foliage of New England, with a mix of green, yellow, and orange leaves against a clear blue sky. This peaceful setting is a highlight for travelers on a New England states road trip, offering a moment of reflection amidst nature's splendor.

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

  • Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
  • Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
  • Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
  • Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
  • A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
  • Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
  • Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
  • Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

amy is wearing a bright orange sweatshirt and holding her toddler son in the air, both are smiling and there is a famous maine lighthouse beyond

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

  • Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
  • Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
  • Grab some of that famous Maine lobster.
  • Stuff your face with Maine potato donuts from local staple The Holy Donut
  • Walk the pretty Old Port and patronize the eclectic shops and restaurants
  • Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
  • Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

A breathtaking aerial view from a cliffside, overlooking a tapestry of fall foliage in New England, with a backdrop of a calm bay meeting the Atlantic Ocean. This panoramic vista captures the essence of exploring New England, where land and sea meet amidst the splendor of autumn.

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

  • Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
  • Order popovers at the Jordan Pond House (delicious!)
  • Take a whale watch or other wildlife tour from Bar Harbor
  • Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
  • Marvel at the natural wonder of Thunder Hole
  • Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

A charming street in a New England town during a getaway, featuring historic brick buildings with a quaint coffee shop, and the steeple of a white church rising against a sky with puffy clouds. The inviting atmosphere is perfect for a leisurely stroll and exploration.

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

  • Strawbery Banke Museum: an outdoor living history museum.
  • Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
  • Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
  • Be surrounded by books and grab a tasty beverage at Book & Bar
  • Wander the lovely Prescott Park
  • Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

READ NEXT   18 Magical New England Christmas Towns that are Straight Out of a Hallmark Movie (Updated 2023)

Day 19: Salem, Massachusetts

A historic dark wood-paneled house in New England, decorated with autumnal pumpkins and hay bales, captures the seasonal charm on a driving tour. The bright fall foliage provides a colorful contrast to the classic architecture, inviting visitors to explore the region's heritage

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

  • Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
  • Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
  • Tour the House of the Seven Gables
  • Walk the neighborhoods around Federal Street and admire the stately historic homes
  • Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
  • Get spooked on a nighttime ghost tour ( top recommendations here !)
  • Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

A classic New England lighthouse with a white facade and adjoining keeper's house, set against a clear blue sky. A well-tended lawn with a concrete pathway leads to the building, symbolizing the maritime heritage encountered while traveling through New England

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

  • 25 Things to Do on Cape Cod (Besides the Beach!)
  • 13 Best Hotels on Cape Cod: Where to Stay on the Cape
  • 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
  • 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

  • Woodstock, VT
  • Waitsfield, VT
  • Lincoln, NH
  • Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

  • Provincetown, MA
  • Newport, RI
  • Providence, RI
  • Stonington, CT
  • Litchfield Hills, CT
  • Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

A scenic road in New Hampshire with a covered bridge and fall foliage

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

  • Hampton Beach
  • Surf Portsmouth , Portsmouth 
  • Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

  • Robert Frost Farm State Park , Derry 
  • Civil War Memorial, Chester
  • Matthew Thornton House, Derry 
  • Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

  • Sabbaday Falls 
  • Albany Covered Bridge 
  • Swift River Lower Falls  
  • Russell-Colbath House 
  • Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

  • George’s Diner , Meredith 
  • Mt. Major Trail, Alton 
  • Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
  • Cotton Valley Rail Trail , Wolfeboro 
  • Abenakee Tower , Tuftonboro

Scenic Drives in Maine

  • Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

  • Lily Bay State Park
  • B52 Crash Site
  • Mount Kineo
  • Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

  • Goose Rocks Beach , Kennebunkport
  • Portland Head Light , Cape Elizabeth
  • Old Orchard Beach Boardwalk, Old Orchard Beach
  • The Holy Donut, Portland
  • Farnsworth Art Museum, Rockland
  • Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

  • Thunder Hole
  • Bar Harbor Inn & Spa

Scenic Drives in Vermont

A close up of the South Vermont 100 sign on a scenic byway in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

  • Molly Stark State Park, Wilmington
  • Dot’s Restaurant , Wilmington
  • The Vermont Country Store ,  Weston
  • Green Mountain Sugar House ,  Ludlow
  • Moss Glen Falls, Granville
  • Ben & Jerry’s Factory , Waterbury
  • Cold Hollow Cider Mill ,  Waterbury Center
  • Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

  • Vermont Country Deli , Brattleboro
  • Creamery Bridge, Brattleboro
  • Southern Vermont Natural History Museum, West Marlboro
  • Hogback Mountain Scenic Lookout, Wilmington
  • Bennington Battle Monument, Bennington
  • The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

  • The Bennington Battle Monument, Bennington
  • The Robert Frost Stone House Museum , Shaftsbury
  • Cider donuts at the Equinox Valley Nursery , Manchester
  • Downtown Murals, Rutland
  • Woodchuck Cider , Middlebury
  • The Burlington Waterfront – Burlington
  • Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

  • Castle Hill Lighthouse
  • Brenton Point State Park
  • Fort Adams Park
  • The Breakers
  • Marble House
  • Rough Point
  • The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

  • Lisbon Meadows Park, Lisbon
  • Prudence Crandall Museum , Waterbury
  • New England Center of Contemporary Art, Brooklyn
  • Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

  • Eat in Little Italy, New Haven
  • Hammonasset Beach State Park, Madison
  • Harvey’s Beach, Old Saybrook
  • Rocky Neck State Park, East Lyme
  • Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

  • Norman Rockwell Museum , Stockbridge
  • Berkshire Botanical Garden,  Stockbridge
  • The Mount, Edith Wharton House , Lenox
  • Berkshire Museum, Pittsfield
  • Hancock Shaker Village, Hancock
  • Mount Greylock , North Adams
  • Massachusetts Museum of Contemporary Art , North Adams
  • Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

  • Hammond Castle Museum, Gloucester
  • Crane Wildlife Refuge, Essex
  • Eat at the Clam Box , Ipswich MA
  • Plum Island Beach, Newburyport
  • Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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16 New England winter getaways

Outside view of Stowe Mountain Resort with hockey rink and Whistling Pig

New England during the winter is whimsical. With its quaint towns, snowy landscapes, and winter festivities, there is plenty of fun to be had. With most destinations situated relatively close together, a family road trip is a great way to experience it all. Find out our favorite New England destinations — which will appeal to skiers and non-skiers alike — in our guide to the best New England winter getaways.

Outside view of Stowe Vermont

1. Stowe, Vermont

Anyone who has visited Stowe in the winter is immediately captivated by its charm. A slow drive along its quaint Main Street, lined with cozy cafes, inviting boutique shops, sparkling lights, and warm restaurants, never fails to leave visitors in awe. If you’re a skier, don’t miss an afternoon on the snowy slopes at Stowe Mountain Resort, just a short drive from town. Non-skiers can take a sleigh ride through its peaceful, powdery landscape, go snowshoeing in the nearby trails, or snowmobile through the forest.

When you’re ready to dine, head to The Bench or The Roost, whose menus include a variety of meals for the whole family to enjoy. Kids will love a chance to build their own snow sculptures while parents enjoy a locally crafted beer or an evening massage. with all the wintry things to do in Stowe, VT , it’s one of our most highly recommended New England winter destinations for a road trip.

2. Newport, Rhode Island

Newport is an ideal New England winter getaway for non-skiers for its rich history and breathtaking views. Take the family for a memorable stroll along the Cliff Walk trail, located right on the coast. From here, warm up on a tour through the opulent, Gilded Age mansions that Newport is renowned for: The Breakers and the Marble House. 

After a day of exploration with the family, treat yourselves to a delicious meal at The Mooring or The Black Pearl, both known for fresh, local seafood. A walk through downtown Newport is a wonderful way to round out your evening before hitting the road in the morning to visit your next destination together.

winter road trips in new england

3. Boston, Massachusetts

Boston comes alive when the temperatures drop, hosting dozens of exciting festivals and seasonal events for everyone in your family. Lace up your skates for a glide across the ice at Frog Pond in Boston Common to get into the winter spirit. For history buffs, the historical landmarks along the Freedom Trail are a must-see on your winter road trip itinerary.

Interested in some day trips in New England in the winter? A rental van offers the chance to visit Cambridge, home to Harvard University, and spooky Salem, known for the famous witch trials. You’re probably hungry by now, and Boston offers everything from seafood at Legal Sea Foods to Italian cuisine in the North End.

4. Portsmouth, New Hampshire

Portsmouth’s beautiful downtown is brimming with eclectic shops, galleries, and restaurants, making it a vibrant stop on a New England winter getaway for non-skiers. Enjoy a family stroll through the streets, adorned with festive decorations during the holiday season.

If you’re feeling active, head to the ice skating rink at Strawbery Banke Museum or catch a show at the Seacoast Repertory Theatre. Load the family in the warm, cozy van for a scenic drive to New Castle, a darling island town with sweeping views of the Atlantic Ocean. 

Heard enough? Let us help you plan your Portsmouth road trip !

winter road trips in new england

5. Bar Harbor, Maine

Looking for classic New England ski resorts? The picturesque village of Bar Harbor offers a picture-perfect winter landscape of white mountains and icy shores. If you and your family love the outdoors, bundle up for some cross-country skiing, snowshoeing, and wildlife watching in Acadia National Park, a must-see on your New England winter getaway and just a short drive away!

After a day in the snow, warm up with a meal together at The Thirsty Whale or Side Street Cafe. We also recommend the 30 minute drive south to see Bass Harbor Head Lighthouse and its coastline views.

6. Woodstock, Vermont

Quaint and historic, Woodstock is an ideal place to experience a New England winter. It’s a great winter getaway for both skiers and non-skiers, so whoever wants to hit the slopes can head to the mountains while the others head to Woodstock Nordic Center for a day of sledding and snowshoeing. 

The town hosts a variety of family-friendly winter festivities, like its famous Woodstock Wassail Weekend. Hungry? The whole family will enjoy hearty, farm-to-table meals at The Prince & The Pauper or comfort food at Worthy Kitchen.

winter road trips in new england

7. North Conway, New Hampshire

Some of the best New England ski resorts can be found in North Conway. You and the family can spend the day skiing or snowboarding together at Cranmore Mountain Resort, or in the iconic White Mountains for snowshoeing and ice climbing.

Don’t miss this classic New England day trip in the winter: head out for a scenic drive to Mount Washington Valley, whose mesmerizing natural beauty will impress even the pickiest of travelers.

8. Kennebunkport, Maine

This lovely coastal town brightens up during the holiday season, with streets and shops graced with sparkling lights. Take the family out for an evening together at Dock Square, the heart of Kennebunkport which explodes with unique boutiques, art galleries, and restaurants. 

It wouldn’t be a proper winter getaway without an afternoon of ice skating at the Waterhouse Center. When hunger hits, there are options for kids and adults alike, from seafood at The Clam Shack to fine dining at Earth at Hidden Pond. Take advantage of your rental van with a must-do New England day trip in the winter to Cape Porpoise Pier. The views of the harbor are worth it.

9. Providence, Rhode Island

Providence is an excellent New England winter getaway for non-skiers and active families. Layer up and hit the ice at the BankNewport City Center for a fun afternoon of winter activity.

Art-loving families will especially enjoy Providence, as it’s home to the Rhode Island School of Design Museum and the Providence Children’s Museum. Be sure to check out WaterFire, a unique art installation that lights up the rivers downtown. When it comes to dining, Providence has something for everyone, from Italian cuisine in Federal Hill to farm-to-table dishes in Downcity.

winter road trips in new england

10. Mystic, Connecticut

A New England winter getaway would not be complete without a visit to the enchanting Mystic Seaport, home to the largest maritime museum in the United States. Kids will love the Lantern Light Tours: an outdoor, self-guided experience showcasing how holiday celebrations have evolved from past to present. Take advantage of Mystic’s proximity to these well-known lighthouses in New England by hopping in the van for a day trip to visit them.

Have you seen Mystic Pizza? Why not download the movie for passengers to watch while on the road to Mystic. Then, surprise the kids with dinner at the real-life Mystic Pizza! 

11. Montpelier, Vermont

It might be the smallest state capital in the country, but that doesn’t mean Montpelier isn’t bursting with life! Take the family ice skating at Central Vermont Memorial Civic Center or head to Hubbard Park’s long, gentle slopes for sledding. 

Once you’ve worked up an appetite, try The Bagel Cafe for delicious sandwiches, soups, and of course, fresh bagels. Then, check out the Vermont State House and its free guided tours of the gold domed capitol building. The views of Montpelier and the surrounding mountains from the top of the dome are spectacular.

12. Burlington, Vermont

Burlington is one of New England’s most vibrant winter destinations. The city hosts several winter festivals, including Vermont Brewers Festival and the Burlington Winter Carnival which includes ice sculpting, snowshoe races, and a parade. The Waterfront Park features an outdoor ice skating rink with panoramic views of Lake Champlain.

There is a great bike path along the Waterfront that the kids are sure to love. Adults, on the other hand, can indulge in some shopping at Church Street Marketplace and dining at Zero Gravity Brewpub or Switchback Brewing Company. A visit to the Shelburne Museum won’t disappoint, and its 45-acre grounds are especially captivating during the winter months.

winter road trips in new england

13. Camden, Maine

Camden is a must on your road trip exploring the best of New England’s ski resorts, as the crown jewel is the Camden Snow Bowl, a ski area nestled in the mountains overlooking Penobscot Bay. If you’re a family of sports lovers, this is your chance to go downhill and cross-country skiing, snowboarding, and tubing together. Non-skiers, in the meantime, can enjoy Harbor Park and its gorgeous views of both the coastline and the snowy islands of Penobscot Bay. 

February’s Winterfest celebration shouldn’t be missed! There will be ice sculpting, snowshoe races, a chili cook-off, live music, and other family-friendly activities. Looking for a nature break? Pile into the van for a short but beautiful drive to Coastal Mountains Nature Trail and Camden Hills State Park, the perfect New England day trip in the winter.

14. Lincoln, New Hampshire

Lincoln’s wintry landscape will captivate you. Skiers will revel in Loon Mountain, a premier ski resort nestled in the heart of the majestic White Mountains. Non-skiers should not miss an afternoon at The Ice Castles, where magical ice formations with intricately carved tunnels, slides, and towers are sure to impress. We highly recommend a visit to Flume Gorge, a narrow granite canyon with cascading waterfalls and scenic trails. It’s a short drive from town and easily accessible by van.

Hungry? Lincoln offers lots of wonderful places to snuggle in for a family meal. There are cozy pubs, family-friendly restaurants, and upscale dining with menus to suit every taste. Leave feeling stuffed, happy and full of love.

15. Bretton Woods, New Hampshire

Nestled in the White Mountains, Bretton Woods is home to the state’s largest ski area, As a top-notch New England ski resort, you will adore its pristine slopes that offer excellent skiing, snowboarding, and magical sleigh rides through the snowy landscape with the whole family.

Fancy an adrenaline rush? Bretton Woods Canopy Tour hosts a thrilling zip-lining experience through the treetops. This is a wonderful memory to make as a family! Take a van ride to the majestic Mount Washington Hotel and its unparalleled views of Mount Washington, the highest peak in the Northeastern United States.

16. Chatham, Massachusetts

If you’re seeking a New England winter getaway without the snow, head to Chatham on Cape Cod. The lovely Main Street is lined with quaint shops and snuggly cafes, where you can warm up with a hot cup of cocoa together. If you’re a family that loves animals, don’t skip the short drive to Monomoy National Wildlife Refuge. 

Speaking of short drives, the iconic Chatham Lighthouse, standing tall against the coastal backdrop, is worth a trip. History lovers will want to make a stop at the Atwood Museum for a fascinating glimpse into Chatham’s past. 

winter road trips in new england

Explore these New England winter destinations in style 

The best way to experience all that New England has to offer is through an exciting road trip with your loved ones. Here are some tips to ensure a smooth and easy winter adventure!

What to pack for your New England adventure

For your New England adventure in the winter, you should pack warm jackets, boots, gloves, hats, long johns, and skis if you plan on skiing. Does lugging all of that to the airport sound exhausting? Renting a van affords you the space you need to bring all your gear, plus cozy extras like blankets, snacks, and pillows for the ride.

Map your ideal route

When mapping your ideal route for your New England winter road trip, consider road conditions and plan scenic stops along the way. Bring along this list of must-see destinations, and prioritize your stops according to the time you have available to explore with your family. Google Maps and Waze are great apps to assist with daily planning, as each will provide warning of road closures or accidents to avoid. 

Talk about the activities that are most important to everyone coming along for the ride through New England’s winter wonderland. If you’re a family of skiers, prioritize destinations like Stowe and Lincoln. If you’re more interested in landscapes and history, destinations like Newport and Chatham will be far more appealing.

Get the right vehicle

Going on a New England winter road trip is truly an unforgettable experience, made better by traveling together in one vehicle. We want to help you turn this idea into a reality by providing comfortable, safe transportation to every stop on the list! We know that the more space you have to relax on the road, the happier everyone will be.

Whether you’re skiing or not, it’s best to maximize the room you have while traveling. More than that, the vehicle for your winter road trip should offer comfort, heating, and winter driving features. This ensures that you’ll spend less time fretting about details and more time talking, laughing, and reminiscing!

Maximize winter whimsy with Greenvans

A spacious van, like those offered by Greenvans, is a great option for a New England vacation in the winter since its fleet is tailored for comfortable and safe winter road trips through any type of weather. Our vans come equipped with heating, cargo space for skis and sleds, and winter-ready tires.

And with offices all over the Northeast U.S., including Providence and Boston, picking up your family van puts you exactly where you need to be. As you can see we like to make things easy, so your cozy family vacation can be all play and no work.

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5 Must-Do Adventures On Your Winter Road Trip Through New England

Escape the city and hit the road.

By: Chris Mongeau + Save to a List

winter road trips in new england

Winter in New England can be brutal, and while this year hasn’t exactly been the worst, it’s still early March and there’s a very good chance we could get hit with more snow and cold spells again. Most people from New England would probably not think of driving around the region for fun in the midst of inclement weather, but if it’s your kind of thing (it’s definitely mine) and you’ve got some decent tires, don’t be afraid to hit the road even if it’s snowing.

I recently did a short loop through some of my favorite spots not far from home and one thing I love the most about winter is the increased feeling of isolation when outdoors. The northeast is a really small place, and unfortunately, even our more remote areas aren’t much more than a few miles from some sort of sign of civilization. In the winter, there’s no one on the trails, the roads are usually empty, and you can definitely count on empty beaches on the coast to watch a sunset. Plus, a good snowfall is worth enduring the cold if you’re into taking photos outdoors.

1. Explore Portland Head Light

winter road trips in new england

Photo: Chris Mongeau Portland Head Light is a great spot to spend a winter afternoon in Maine and catch the sunset. Located on Cape Elizabeth, Portland Head Light is a short 15-minute drive from downtown Portland. There’s a trail that goes along the cliffs here and you can climb down to a rocky beach area when the tide is lower. It can get pretty windy here during every season, so definitely dress warm even if it doesn’t seem cold out. Afterwards, head back into town for an incredible burger and some beers at The Great Lost Bear in Portland. Learn more.

2. Explore the Basin in Franconia Notch SP

winter road trips in new england

Photo: Chris Mongeau The Basin is an enormous, granite pothole that has been eroded by the Pemigewasset River over 15,000 years. Located just off I-93, there are a few hiking trails here that are maintained throughout the winter. Often times during cold spells, parts of the cascading river will freeze, which makes for really stunning photographs. The trail to the basin itself is mostly flat with a few slight grades and if you’re into hiking longer distances in the snow, you can even take the 2.5 mile trail Cascade Brook Trail all the way to Lonesome Lake. Learn more.

3. Hike the Flume Gorge in Franconia Notch SP

winter road trips in new england

Photo: Chris Mongeau The Flume Gorge is located just two miles south of the Basin on I-93. In the wintertime, the Flume Gorge is technically closed for the season, but you can still walk the trails leading up to the boardwalk inside of the gorge. With the boardwalk removed, you can’t hike through the whole gorge, but you can get some really breathtaking views of icy cliff sides and the picturesque covered bridge over the Pemigewasset River. Learn more.

4. Drive Around Newfound Lake

winter road trips in new england

Photo: Chris Mongeau Newfound Lake is my favorite of New Hampshire’s Lake Region. Located in central New Hampshire, Newfound Lake is about an hour south of Franconia State Park and directly on the way to points north off I-93. I spent many summers and winters on this lake as a kid, and it used to freeze during the wintertime (great for snowmobiling, ice fishing, snowshoeing and cross country skiing), but it doesn’t seem to as often anymore. Newfound Lake in the winter is quiet and peaceful. The road that loops around the lake is well worth a drive to catch views of snowy mountains in the distance and quaint lakeside cabins. Learn more.

5. Hike the Coffeehouse Loop in Douglas State Forest

winter road trips in new england

Photo: Chris Mongeau Douglas State Forest is located in central Massachusetts in the Blackstone River Valley corridor. This state forest is home to Wallum Lake, where there are a few hiking trails that are great in the wintertime. My personal favorite is the Coffeehouse Loop Trail, which is a 2-mile loop that goes by the site of an old saw and grist mill. You can also hop on the Southern New England Trunkline Trail from here, which is open to walkers, cross-country skiers, cyclists and equestrians. The 22-mile trail passes through Douglas, Uxbridge, Millville, Blackstone, Bellingham, and Franklin, and is one of the longest trails in southern Massachusetts. Learn more.

Cover photo: Chris Mongeau

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9 New England Road Trip Itineraries for Any Season

Whether it’s spring, summer, fall, or winter, there’s a road trip (or two) for each season..

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Distant view from water of large historic house on coast

View of Horsehead-Marbella, an historic house near Beavertail State Park.

Photo by Trevor Fairbank/Shutterstock

New England may be known for its autumn reds and yellows, but to us, there’s no bad time to cross the region by car. Officially consisting of the six states of Maine , Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, New England is filled with picturesque seaside towns, mountains, clear lakes, and yep, some of the best fall foliage around. To see the region’s most beautiful sites, head out on one of these great New England road trip itineraries.

1. Vermont 100

  • Start: Heartwellville
  • Distance: 200 miles
  • Recommended season: summer

At 200 miles long, the Scenic Route 100 Byway hugs the eastern edge of the Green Mountains and travels nearly the entire length of Vermont. (Most of Vermont’s ski resorts are located along the highway, so it can actually have fewer cars in the summer than winter.) Cute country stores your thing? Be sure to stop at Vermont Country Store in Weston—it’s been open since 1946 and offers free cheese and maple syrup samples.

Rocky cove along Maine’s coast, with a few evergreens

Dramatic scenes like these are par for the course along Maine’s coast.

Photo by Shutterstock

2. Coastal Maine

  • Start: Ogunquit
  • End: Calais
  • Distance: 272 miles

Much like California , Maine is also known for its stretch of Route 1, aka “the lobster trail.” This trip crawls along the coastline and passes through Ogunquit, Kennebunk, Portland, Rockport, and more until it hits Canada. Must-dos along the way: Eat at the Clam Shack , on the bridge between Kennebunk and Kennebunkport, snap a photo for the ’gram at Portland Head Light, and visit Project Puffin Visitor Center in Rockland—especially fun with kids in tow.

Dunes in Cape Cod, MA at sunset with a small group of people in the background

Cape Cod is known for its beautiful beaches and coast line.

VALORIE DARLING/Valorie Darling

3. Old King’s Highway in Cape Cod

  • Start: Sandwich
  • End: Provincetown
  • Distance: 60 miles

Route 6A is popular in summer, when visitors to the Massachusetts Cape begin their trip in Sandwich and follow the road east to Provincetown, passing cranberry bogs, salt marshes, historic homes, and some of the oldest villages in the United States. Get your lobster roll fix at places like Kate’s Seafood (Brewster) and Arnold’s Lobster & Clam Bar (Eastham). For overnights, head over to South Dennis and stay at the Sesuit Harbor House , originally built in 1735.

Aerial view of the Kancamagus Highway curving through red, yellow, and green forest

The Kancamagus Highway is known for being one of the top spots to see fall foliage.

4. Kancamagus Highway, New Hampshire

  • Start: Conway
  • End: Lincoln
  • Distance: 34.5 miles
  • Recommended season: fall

Curving for 34.5 miles on country roads through New Hampshire’s White Mountain National Forest, this drive has earned its place on several “best of” road trip lists, thanks to its picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year. With the highway’s plentiful hiking trails taking up daylight, spend the night in one of the six White Mountain National Forest campgrounds located on the byway.

A view of the small town, St. Johnsbury, Vermont in the fall with green and orange trees in the foreground and two white buildings with towers in the background.

This road trip passes through quaint towns like St. Johnsbury, Vermont.

SNEHIT PHOTO/Shutterstock

5. Connecticut River Byway

  • Start: South Hadley, Massachusetts
  • End: Pittsburg, New Hampshire
  • Distance: 242 miles

Another way to reach New Hampshire’s White Mountains is to take the Connecticut River Byway , which is Vermont’s only designated National Byway. Along the way, stop by some of Massachusetts’s historic district villages like Northfield and Montague Center, or take some nature-led detours to Molly State Park in Vermont.

If you’re unable to do the whole route, no worries. In the words of AFAR editor Tim Chester : “Pick a stretch and you can’t go wrong—particularly in fall when the leafy backdrop is painted shades of red, orange, and yellow.”

A view of the church and a wide, red brick road in Burlington, Vermont Church Street Marketplace downtown city. Fall trees that are orange and yellow line the road on the right and left side.

End your road trip in Burlington, Vermont’s capital.

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6. Burlington to Woodstock, Vermont

  • Start: Burlington
  • End: Woodstock
  • Distance: 132 miles

While several road trips on this list go through Vermont, this road trip itinerary specifically focuses on the state’s delicious dishes . Starting in Burlington, road-trippers can visit the local farmers’ market for breakfast before continuing south on Route 89 to Stowe. Around here, try concepts like Long Trail Brewing Company and Hen of the Wood. The drive concludes in Woodstock, offering local fare from Fat Toad Farm.

7. Mohawk Trail, Massachusetts

  • Start: Pittsfield
  • End: Greenfield
  • Distance: 63 miles

Massachusetts’s Berkshire Mountains and its famed 63-mile Mohawk Trail are the stuff of leaf-peeping legends . Starting in Pittsfield, take Route 7 north until hitting Williamstown, home to Williams College, and continue on Route 2 to Western Gateway Heritage State Park, Natural Bridge State Park, and MASS MoCA, among other attractions. Eventually, you’ll hit the Hoosac Range—where the views only keep getting better. For a stay along the way, consider the Tourists hotel in North Adams.

Winter in Stowe, Vermont, with a few skiers and ski lift among snowy evergreens

Winter in Stowe, Vermont, one of the leading ski destinations on the East Coast

8. Skiers’ Paradise, Vermont

  • Start: Stowe
  • Distance: 80 miles
  • Recommended season: winter

Come winter, heavy snow drifts mean good things for skiers in New England. Visit two of the best ski resorts on the East Coast on this road trip, which starts in Stowe and finishes in Woodstock, Vermont. It’s a mere 80 miles between the two towns, but the slopes—and attractions—in each mean you’ll want to spread the trip out over a long weekend. Things not to miss in Stowe: the family-run Alchemist brewery, Stowe Maple Products sugarhouse, and the thin-crust pies at the aptly named Piecasso .

In Woodstock, be sure to carve out time for Richardson’s Tavern , Billings Farm & Museum , and F.H. Gillingham & Sons , a store that has been open for more than 130 years.

9. Quiet Connecticut

  • Start: Norwich
  • Distance: 40 miles
  • Recommended season: spring

If you’re a fan of quaint towns and farmsteads, this road trip from Norwich to Woodstock might be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) The road clocks in at 40 miles, you’ll want to slow down and take your time—yep, it’s that scenic. Do some birdwatching at Aicher Preserve or Border Woods Preserve before staying at the Inn At Woodstock Hill , where you can enjoy Connecticut’s serenity near the small town of Putnam. Tranquility, is that you?

This article originally appeared online in 2020; it was most recently updated on August 9, 2023, to include current information.

A woman laying in a super bloom of golden California poppies in Antelope Valley

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71 BEST Tips New England Winter Road Trip (Selected)

New England Winter Road Trip

  • New England Winter Trip
  • Winter Hiking Trails
  • Skiing and Snowboarding
  • Historic Landmarks
  • Festivals and Events
  • Charming Bed and Breakfasts
  • Culinary Experiences
  • FAQs (Frequently Asked Questions)
  • Please note

Winter in New England is a magical time of year.

With its picturesque landscapes, charming towns, and abundance of outdoor activities, this region offers a unique and unforgettable winter experience.

Whether you're a nature enthusiast, a history buff, or simply looking to escape the hustle and bustle of everyday life, a winter trip to New England has something for everyone.

Exploring Nature

New England boasts a plethora of stunning hiking trails that take on a whole new beauty in the winter. Bundle up and head out to experience the serene landscapes blanketed in snow.

Some popular winter hiking trails include:

Mount Washington, New Hampshire: Known for its challenging conditions, this trail offers breathtaking views and a true test of endurance.

Franconia Ridge Loop, New Hampshire: This loop trail takes you through an alpine wonderland and offers panoramic views of the surrounding mountains.

Acadia National Park, Maine: Discover frozen waterfalls, snow-covered forests, and coastal scenery on the various trails within this national park.

New England is renowned for its world-class ski resorts. Whether you're a seasoned pro or a beginner, hitting the slopes is a must-do activity during your winter trip.

Here are some top ski resorts in the region:

Killington Resort, Vermont: With its extensive trail network and state-of-the-art facilities, Killington is a haven for skiers and snowboarders of all levels.

Sunday River, Maine: Boasting eight interconnected peaks, this resort offers a variety of terrain and an exhilarating skiing experience.

Stowe Mountain Resort, Vermont: Known for its challenging trails and stunning views, Stowe is a favorite among advanced skiers.

Immerse in History and Culture

New England is steeped in history, and winter provides a unique opportunity to explore its rich cultural heritage.

Visit historic landmarks such as:

Plimoth Plantation, Massachusetts: Step back in time and experience life as it was in the 17th century at this living history museum.

Old Sturbridge Village, Massachusetts: Explore a recreated 19th-century New England village and learn about traditional crafts and daily life.

Mystic Seaport Museum, Connecticut: Delve into maritime history at this living history museum featuring historic ships and exhibits.

Winter is a season of celebration in New England, with numerous festivals and events taking place.

Don't miss out on the following:

First Night Boston: Ring in the New Year with live performances, art exhibits, and a magnificent fireworks display in the heart of Boston.

Ice Sculpture Festival, Vermont: Marvel at intricate ice sculptures created by talented artists during this annual event.

Newport Winter Festival, Rhode Island: Enjoy live music, food tastings, and a dazzling ice carving competition in the historic city of Newport.

Cozy Retreats and Culinary Delights

Escape the cold and cozy up in one of New England's charming bed and breakfasts. These establishments offer warm hospitality and a home-away-from-home experience.

Some notable B&Bs include:

The Inn at Thorn Hill, New Hampshire: Nestled in the White Mountains, this luxurious B&B offers stunning views and gourmet dining.

Captain Fairfield Inn, Maine: Located in the picturesque town of Kennebunkport, this inn combines historic charm with modern amenities.

The Pitcher Inn, Vermont: Set in the quaint village of Warren, this inn features uniquely themed rooms and a renowned farm-to-table restaurant.

New England is a food lover's paradise, especially during the winter season. Indulge in regional specialties such as:

Clam Chowder : Sample this creamy New England classic, made with fresh clams, potatoes, onions, and cream.

Lobster Rolls : Enjoy a delicious sandwich filled with succulent chunks of lobster meat and served on a buttery roll.

Maple Syrup : Explore sugarhouses and taste the pure sweetness of freshly harvested maple syrup.

Q: What is the best time to visit New England for a winter trip?

A: The winter season in New England typically lasts from December to February, making it an ideal time to visit for a winter trip.

Q: Is New England a good destination for outdoor activities during the winter?

A: Yes, New England offers a wide range of outdoor activities during the winter, such as skiing, snowboarding, snowshoeing, and winter hiking.

Q: What are some popular ski resorts in New England?

A: Some popular ski resorts in New England include Killington Resort in Vermont, Sunday River in Maine, and Stowe Mountain Resort in Vermont.

Q: Are there any winter festivals or events in New England?

A: Yes, New England hosts various winter festivals and events, such as First Night Boston, the Ice Sculpture Festival in Vermont, and the Newport Winter Festival in Rhode Island.

Q: What are some must-visit historic landmarks in New England during the winter?

A: Some must-visit historic landmarks in New England during the winter include Plimoth Plantation in Massachusetts, Old Sturbridge Village in Massachusetts, and Mystic Seaport Museum in Connecticut.

Q: Can I go hiking in New England during the winter?

A: Yes, winter hiking is popular in New England. However, it is important to be prepared, have proper equipment, and check trail conditions before heading out.

Q: What is the weather like in New England during the winter?

A: The weather in New England during the winter can vary, but it is generally cold with temperatures often dropping below freezing. Snowfall is common, creating a picturesque winter wonderland.

Q: Are there any specific clothing recommendations for a New England winter trip?

A: It is recommended to dress in layers and wear warm winter clothing, including a heavy coat, hat, gloves, scarf, and waterproof boots.

Q: What are some popular winter hiking trails in New England?

A: Some popular winter hiking trails in New England include Mount Washington in New Hampshire, Franconia Ridge Loop in New Hampshire, and various trails in Acadia National Park in Maine.

Q: Can I go ice skating in New England during the winter?

A: Absolutely! Many cities and towns in New England have outdoor ice skating rinks where you can enjoy this classic winter activity.

Q: Are there any scenic drives to take in New England during the winter?

A: Yes, the Kancamagus Highway in New Hampshire and the Mohawk Trail in Massachusetts are two scenic drives that offer stunning winter vistas.

Q: Can I visit lighthouses in New England during the winter?

A: Yes, many lighthouses in New England are open year-round, allowing visitors to explore and enjoy the winter coastal scenery.

Q: Are there any special holiday events in New England during the winter?

A: Yes, many towns and cities in New England hold special holiday events and festivals, such as holiday parades, tree lighting ceremonies, and Christmas markets.

Q: What are some charming towns to visit in New England during the winter?

A: Some charming towns to visit in New England during the winter include Woodstock in Vermont, Kennebunkport in Maine, and Newport in Rhode Island.

Q: Can I go snowboarding or skiing in New England if I'm a beginner?

A: Yes, New England ski resorts cater to all skill levels, including beginners. They offer lessons and beginner-friendly slopes to help you get started.

Q: Are there any indoor attractions to visit in New England during the winter?

A: Yes, New England has several indoor attractions, such as museums, art galleries, and historic sites, where you can escape the cold and still enjoy your trip.

Q: Can I go whale watching in New England during the winter?

A: Whale watching tours typically operate from spring to fall, so it may be challenging to find whale watching opportunities during the winter season.

Q: Are there any culinary specialties to try in New England during the winter?

A: Yes, some culinary specialties to try in New England during the winter include clam chowder, lobster rolls, and maple syrup.

Q: Can I visit national parks in New England during the winter?

A: Yes, many national parks in New England, such as Acadia National Park in Maine, are open year-round, allowing visitors to explore their beauty during the winter season.

Q: Is it necessary to rent a car for a winter trip to New England?

A: Renting a car can offer more flexibility and convenience when exploring New England, especially during the winter when public transportation options may be limited in certain areas.

Q: Can I see fall foliage during a winter trip to New England?

A: No, fall foliage occurs in New England during the autumn months, typically from September to November.

Q: Are there any restrictions or guidelines for traveling to New England during the winter?

A: It's always advisable to check for any travel restrictions, road closures, and weather advisories before planning your trip. Additionally, it's important to be prepared for winter driving conditions if you're driving to New England.

Q: Are there any winter activities for families with young children in New England?

A: Yes, many ski resorts offer family-friendly activities, such as tubing, ice skating, and sleigh rides. There are also indoor attractions like children's museums and indoor water parks suitable for young children.

Q: Can I visit New England for a day trip from nearby cities?

A: While it is possible to visit New England for a day trip from nearby cities, it is recommended to plan for at least a few days to fully experience the region's attractions and activities.

Q: Are there any special New Year's Eve celebrations in New England?

A: Yes, many cities in New England, including Boston, Providence, and Portland, hold special New Year's Eve celebrations with fireworks, concerts, and other festive events.

Q: Are there any discounts or deals available for accommodations or attractions during the winter season?

A: Some accommodations and attractions in New England may offer winter discounts or packages. It is worth checking their websites or contacting them directly for any available deals.

Q: Can I go sledding or snow tubing in New England during the winter?

A: Yes, there are many designated sledding hills and snow tubing parks in New England where you can enjoy these fun winter activities.

Q: What are some scenic spots for photography during a New England winter trip?

A: Scenic spots for photography during a New England winter trip include covered bridges, frozen waterfalls, snow-covered landscapes, and coastal areas.

Q: Are there any Christmas markets or holiday craft fairs in New England?

A: Yes, many towns and cities in New England host Christmas markets and holiday craft fairs where you can find unique gifts, decorations, and festive treats.

Q: Can I go cross-country skiing or snowshoeing in New England?

A: Yes, there are numerous trails and parks in New England that cater specifically to cross-country skiing and snowshoeing enthusiasts.

Q: Are there any cultural events or performances happening in New England during the winter?

A: Yes, New England has a vibrant arts and cultural scene, with theaters, music venues, and art galleries hosting performances and exhibits throughout the winter season.

Q: Can I visit historical homes and mansions in New England during the winter?

A: Some historical homes and mansions in New England may have limited access or specific visiting hours during the winter, so it's best to check their schedules in advance.

Q: What is the average snowfall in New England during the winter?

A: Snowfall amounts in New England can vary, but on average, the region receives significant snowfall during the winter months.

Q: Can I go ice fishing in New England during the winter?

A: Yes, ice fishing is a popular winter activity in New England. However, it is important to ensure the ice is safe and to follow all local regulations and safety guidelines.

Q: Are there any scenic train rides available in New England during the winter?

A: Yes, some scenic train rides operate during the winter season, offering picturesque views of snow-covered landscapes.

Q: Can I visit wineries or breweries in New England during the winter?

A: Yes, many wineries and breweries in New England remain open during the winter, offering tastings and tours.

Q: Are there any indoor water parks or swimming pools in New England?

A: Yes, there are several indoor water parks and swimming pools in New England where you can enjoy aquatic fun even during the winter months.

Q: Can I go dog sledding in New England during the winter?

A: Yes, there are dog sledding experiences available in certain parts of New England, allowing you to enjoy this unique winter activity.

Q: Can I visit coastal areas in New England during the winter?

A: Coastal areas in New England can be visited during the winter. While some beach towns may have limited services, you can still enjoy walks on the beach and the beauty of the winter coastline.

Q: Can I go birdwatching in New England during the winter?

A: Yes, New England offers opportunities for winter birdwatching, as many bird species remain in the region during the colder months.

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A winter trip to New England offers a diverse range of experiences, from outdoor adventures to cultural immersion and culinary delights.

Embrace the beauty of the region's winter landscapes, delve into its rich history, and savor the warmth and charm of its cozy retreats.

Whether you're seeking adventure or relaxation, New England has it all, making it the perfect destination for an unforgettable winter getaway.

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New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  November 8, 2022

The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options!) 2024

Having traveled through the entire New England region for 10+ years, I’ve been able to get a strong understanding on the best things to do, and I’m so thrilled that I’ve finally developed my ultimate 7 Day New England Itinerary to share with you!

A 7-day itinerary to tour New England has been one of my most requested topics, and I totally understand why. It’s so hard to look at a region comprised of 6 gorgeous states, and try to figure out what’s worth your time, and what you can leave out. While I think everything is pretty much worth your time in New England (I’m a bit bias!), this itinerary focuses on the best of the best, and also takes into consideration efficiency so you have as much time as possible to also enjoy your destinations.

This itinerary is also geared toward those who are visiting New England for the first time. With that, let’s get into it, shall we?

Pebble Beach is along the Ocean Path trail in Acadia National Park, and is definitely one of the best stops to add to a 7 day New England road trip itinerary.

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

How Many Days Do You Need In New England?

You can easily spend anywhere from 1 day to a month in New England, so this entirely depends on how much time you really have to dedicate to your trip. This post will prove that you can easily see some of the best things in this region with my 7 Day New England road trip itinerary.

But, that said, more is always more when it comes to time to travel, right? So of course, you can easily turn this itinerary into a 10-day adventure, or even two weeks. Under my 10 Day New England road trip itinerary option, you’ll see that I’ve made notes on side excursions where you can easily add in a day or two to extend your trip even further.

And of course, you can definitely see some of the best places in just 5 days, and I’ve included a 5-Day option at the very end for those who don’t have as much time (and don’t worry, it’s still pretty great!).

My motto is always, “Even if I just have one day, it’s better than not going at all,” so whatever time you have for your trip with definitely be worth it.

Where To Start A 7 Day New England Road Trip Itinerary?

For any road trip through this region, Boston is the best place to start, especially if you’re flying in. Boston Logan International Airport typically offers the cheapest flights to this area, and is also a worthy destination to explore on its own.

Not only that, it’s also incredibly convenient to most places in New England, and is just the easiest starting point. For that reason, pretty much all of my itineraries on this website start in Boston.

Boston is one of the best places to start when planning out your 7 day New England road trip itinerary.

If you’re not flying in, however, and already live in this area, or are driving in from nearby, Boston is still a great starting point (especially if you’ve never been!). But you can definitely adjust this itinerary to start from anywhere in New England that best suits your needs.

The only time I would suggest using a place like Portland, Maine as your starting point if if you plan to really only explore the northern areas of New England, like the rest of Maine or New Hampshire. But even in that case, Boston is still just as convenient, so it will then simply depend on personal preference at that point.

7 Day New England Road Trip Itinerary

Notes About This Itinerary

For some stops along this route, I also suggest other options to really help you create the ultimate road trip for you based on your preferences. So keep an eye out for those, and get ready to take some notes!

This 7 Day New England road trip itinerary also follows a true road trip style , meaning you’ll be in a different town each night of your stay (with one exception, which you’ll see below). You can certainly tweak that to your liking if you prefer to stay in one place for two or more nights – do what feels right for you.

Lastly, this itinerary was intended to show you around all the different landscapes New England has to offer, so I wanted to include a mix of urban, countryside, mountains and coastal to show you the very best of it all. I also focused on locations that are largely perfect to visit year-round, so seasonality was not factored in.

Old Port in Portland is one of the best neighborhoods to visit.

Day 1: Boston

Boston is one of my all-time favorite cities, and even though for me, the drive to both Boston and NYC is the same, I always choose to visit Boston. I love that it feels like an exciting city, but is also incredibly charming, historic and packed with character. There’s just something very cozy about it, and it’s most definitely worth a day during your trip. It’s also the perfect place to start your 7 Day New England road trip!

Here are some awesome things to consider doing on your day in Boston:

  • Walk the Freedom Trail.
  • Meander through my two favorite neighborhoods: Beacon Hill & the North End.
  • Stroll along the waterfront areas – the Charles Esplanade is especially beautiful!
  • Walk through the Public Gardens – the bridge is such a great spot for gorgeous photos.
  • Eat, eat, and then eat some more. The culinary scene in Boston is incredible, and seafood here is a specialty.
  • Grab some cannoli at Mike’s Pastry.

When you only have a day, I always suggest considering a tour with a local expert . Especially if you’re a history buff, since there’s so much incredible history at every corner in this city. Boston also has some amazing food tours, too, which I highly recommend. Check out a few of my best suggestions for tours below:

Click here to check out an amazing small-group tour of the historic Freedom Trail!

Click here to check out this awesome North End food walking tour!

Beacon Hill is one of the most charming and picturesque places in Boston.

Hotel suggestions in Boston:

Splurge: Boston Harbor Hotel . A 5-star waterfront hotel that’s more than worth the splurge to kick start your amazing road trip through New England. The location is also convenient to a lot of attractions.

Moderate: The Eliot Hotel . A great location in the beautiful Back Bay neighborhood with opulent rooms.

Budget: HI Boston Hostel . Boston is typically an expensive city to visit unless you’re coming in the winter, and this hostel is a great option to save some money during your stay. It also has an awesome location.

Day 2: Woodstock, Vermont (2h 15m From Boston)

Why Woodstock Next? No trip to New England is complete without a stop in a charming Vermont town, and Woodstock is the best of the best when it comes to charm and character. It’s also home to “Vermont’s most beautiful address,” which I’ll tell you about under the suggestions on where to stay.

Here are some awesome things to do in Woodstock, VT:

  • Meander through the most adorable village where all the shops and restaurants are.
  • Visit the three covered bridges: Middle, Taftsville and Lincoln.
  • Explore Billings Farm & Museum.
  • Taste local maple syrups and cheeses at Sugarbush Farms.

Click here to read my post on all the best things to do in Woodstock, VT to help you plan even more!

Woodstock, VT is one of the more charming day trips from Providence, RI to take, especially in the fall season. It's also an amazing destnation to add to your 7 day New England road trip itinerary.

Where to stay in Woodstock, VT :

Luxury option : Woodstock Inn & Resort (Vermont’s most beautiful address!). It’s a splurge, but located right in town, and the perfect way to treat yourself for a 1 night stay.

Moderate: 506 On The River Inn . Very beautiful hotel that’s right on the river and feels cozy.

Budget : The Vesper . A cute little B&B with modern rooms, great prices and walkable to the village.

Pro Tip : Woodstock tends to be an expensive place to visit, so if you’re on a budget, the nearby town of Quechee is a great alternative, and is only about 15 minutes from Woodstock. Quechee is also very cute and I love visiting both towns when I’m in the area.

Alternative Option: If you would prefer to spend 2 nights in Boston and skip Woodstock, you can most definitely do that. Boston is a great place for day trips to other nearby areas, including Cape Cod and Salem. A ferry will take you from Boston to Provincetown on Cape Cod, and to Salem, so you still won’t need to pick-up your rental car right away if you choose this option.

Click here to check out ferries from Boston to Provincetown!

Click here to check out ferries from Boston to Salem!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Salem makes for an easy day trip by ferry from Boston, and this is definitely something to consider as you plan your 7 day New England road trip itinerary.

Pro Tip : Ferries are seasonal, and typically stop running in November or earlier. Be sure to plan accordingly!

Day 3: The White Mountains, New Hampshire (1h 30m From Woodstock)

Why White Mountains Next? They’re on the way to Acadia National Park (which is the next stop!), and they’re very worth your time ( especially if you’re traveling in the fall season). The White Mountains are home to a great mix of cute towns, epic mountain views and amazing parks.

Here are some awesome things to do in the White Mountains:

  • Explore Franconia Notch State Park , and with 1 day, I suggest prioritizing Flume Gorge, which is perfect for all ages, and one of the most popular attractions in the entire state that’s worth your time.
  • If you’re looking for a fun hike, the Artist Bluff Trail offers incredible views of Echo Lake.
  • Ride the Cannon Mountain Aerial Tramway to the mountain’s summit for awesome views.
  • Explore The Basin, which is very close to Flume Gorge, and is very quick and easy.

Littleton is one of my favorite towns to stay in when adventuring through the White Mountains because it offers a cute Main Street and scenic views along the river.

Where to stay in the White Mountains? I highly suggest Littleton . It’s a charming little town with awesome shops and restaurants (it’s often regarded as having one of the best Main Streets in the U.S.!), and it’s also very close to some of the top must-see things from my list above, making it super convenient and efficient for 1 day.

Hotel suggestions in Littleton :

Thayers Inn : Located right on Main Street in the heart of downtown, and very cozy.

Hampton Inn : A nice option that’s on the commercial side of town, but very close to the highway to get around quicker.

Pro Tip: You’ll drive right past Hanover, NH on your way from Woodstock, which is home to Dartmouth College, and is a really adorable little town to stop in for lunch or to take a driving break. Right in the same area is Norwich, VT, which is home to the King Arthur Baking Company campus , and is a really fun spot to pick up some baked goods (especially breads and pastries!) and also have lunch outside on their lawn.

Here are some posts you may find helpful while you plan your time in the White Mountains:

  • Things To Do In Franconia, NH
  • Things To Do In Littleton, NH

Days 4-5: Acadia National Park & Bar Harbor (4h 30m From The White Mountains)

Why Acadia National Park & Bar Harbor Next? Acadia is one of the most incredible and iconic destinations in the Northeast, and even though it’s pretty far north, it’s so worth it for the stunning views. I’ve budgeted two nights here because your drive from the White Mountains to Acadia is a bit longer, and because Acadia just warrants extra time.

The top of Cadillac Mountain at sunset. Acadia National Park is definitely worth adding to your 7 day New England Itinerary.

Here are some awesome things to do in Acadia National Park for a short trip:

  • Walk Ocean Path , which connects Sand Beach to the Otter Cliffs. This is the perfect scenic walk to tackle with a short amount of time because it’s easy, and offers some of the best and most iconic views of the coastline.
  • Thunder Hole is along Ocean Path, and if you’re there on a windy day, the waves will crash so loudly that it sounds like thunder.
  • If you’d like to tackle a hike, a nice one for a quick visit to the park is Great Head . This starts at Sand Beach, and is pretty easy (with some rock scrambling at the beginning), but offers incredible views along the way). After this, you can walk back across Sand Beach and do the Ocean Path for the perfect day in Acadia.
  • Lunch at the Jordan Pond Restaurant is also really fun, and a more relaxing way to spend some of your time in the park. It’s open seasonally only, so plan accordingly, and is famous for their popovers, and incredible views of the famous Bubble Rocks.
  • Sunrise at Cadillac Mountain is one of the most popular things to do, and definitely worth your time! This is another great reason to spend two nights here. Note : Reservations are now required when taking the auto road to Cadillac Mountain’s summit mid-May through October . Click here for more info!
  • Cover more ground by renting E-bikes to explore the park!

Click here for more info on renting E-bikes for your trip to Acadia!

Where to stay in Acadia National Park? Bar Harbor! This lovely little coastal town is the gateway to Acadia, and where most people stay when exploring the park. This is another reason why I’ve given you two days because Bar Harbor is also a worthy town to explore on its town.

Bar Harbor is the best town to stay in when visiting Acadia National Park.

Hotel Suggestions in Bar Harbor :

Bar Harbor Villager Motel : An awesome motel in the center of Bar Harbor’s village, with spacious and updated rooms, and the ability to walk everywhere in town.

Little Fig : A wonderful option if you’re looking for something that’s a bit more stylish because this place is beautifully decorated, and is also walkable to the village.

Click here to read my perfect Acadia National Park Itinerary!

Pro Tip : When driving from Littleton to Acadia, I suggest driving to Lincoln, NH first, and then taking Route 112 to Conway, which is the famous Kancamagus Scenic Highway. This drive takes you through the heart of the White Mountains with some really nice overlooks to stop at, and only adds 30 extra minutes to your drive (plus extra time for any stops you make).

Pro Tip : The Kancamagus Scenic Highway does not have bathrooms, gas stations or cell service, so plan accordingly!

Day 6: Portland, Maine (3h From Bar Harbor)

Why Portland Next? Not only is Portland a very cool city with lots of history and an awesome culinary scene, it’s also on the drive back toward Boston. This is where you’ll begin to make your way back to your starting point. Portland also has a great mix of urban vibes and relaxing coastline to enjoy, so it offers the best of both worlds.

Old Port in Portland, Maine is one of the most charming areas of the city.

Here are some awesome things to do in Portland:

  • See all 3 of Portland’s lighthouses . If you only have time for one, however, make it Portland Head Lighthouse. This is one of the best lighthouses in New England, and definitely worth your time! But keep in mind that the other two lighthouses (Bug Light and Spring Point Ledge Light) are a very short drive away, so it’s easy to see all three in a few hours at most.
  • Go beer tasting . Portland is home to some of the best breweries in New England!
  • Wander through Old Port , the most historic and charming part of the city.
  • Dive deep into the culinary scene , which is best done with a guided tour!
  • Get out onto the water! Portland has tons of boat tours along Casco Bay that are incredibly scenic.

Click here to check out this awesome culinary walking tour of Portland!

Click here to check out this fun tall ship boat tour from Portland!

Portland Head Lighthouse is one of the most iconic sites in all of New England.

Hotel Suggestions in Portland:

Splurge : The Press Hotel . It’s right on the water and in the center of Old Port, making this an awesome hotel to splurge on for a fancier stay in Portland.

Moderate: Cambria Hotel . Also in the Old Port district, this lovely hotel has modern rooms and a great location.

Budget: Black Elephant Hostel . Portland tends to be a pricey city to visit, and even though this is the only hostel in the city, it’s incredibly well-regarded, and will be significantly less expensive than a hotel.

Pro Tip : If you would rather spend your first day in Portland exploring the city, you can do the lighthouses the next morning on your way back to Boston. The lighthouses are located outside of the city’s downtown in South Portland, which you’ll pass through on your drive to Boston.

Click here to check out my guide on the best breweries in Portland, Maine!

Day 7: Back To Boston With Stops Along The North Shore (2h Without Stops)

Why The North Shore Next? As you make your way back to Boston, you’ll drive down the Massachusetts North Shore, which is packed with gorgeous and charming little coastal New England towns . These towns are all pretty close to another, too, which makes it easy to stop in quite a few during your drive. These towns are actually some of my favorites in all of New England.

Here are some more towns you can choose to stop in on your drive back to Boston:

  • Portsmouth, NH – while not technically part of the North Shore, it’s along the route, and a very beautiful coastal city with awesome shopping and restaurants.
  • Newburyport, MA – Some of the best shopping in New England can be found here in Market Square and Tannery Marketplace. It’s also home to Plum Island.
  • Rockport, MA – One of my all-time favorite coastal towns because it’s so unique and loaded with character. This one is a bit of a detour off the main route, but not by much (and worth it, in my opinion).
  • Gloucester, MA – Another gorgeous coastal town that makes for a scenic stop.
  • Salem, MA – Most known for its Halloween celebrations, but is a very beautiful and charming city that’s awesome year-round.
  • Marblehead, MA – An underrated town that’s very beautiful and historic, and loaded with gorgeous coastline.

Rockport, MA is one of the best stops to make when driving from Portland to Boston, and should definitely be a place to consider adding to your 7 day New England road rip itinerary.

Here are some posts that will help you plan your drive down the North Shore:

  • Best Things To Do On Cape Anne (part of the North Shore)
  • Best Things To Do In Marblehead, MA
  • Best Things To Do In Rockport, MA
  • Best Stops To Make Driving Boston To Portland, Maine
  • Best Things To Do In Newburyport & Plum Island

Alternative option : There are also some amazing coastal towns south of Portland that you’ll pass by on your drive back to Boston, including Ogunquit and Kennebunkport . These also make for very fun ways to spend an afternoon. It won’t be possible to see them all in a day, but whichever you choose, know that it’ll make for a wonderful day. All of these places are beautiful.

Click here to read my post on things to do in Ogunquit!

10 Day New England Road Trip Itinerary

With 10 days for your New England road trip, we can pack even more exciting places to visit into your itinerary!

I’ve broken down this 10 Day New England road trip itinerary for you below, and since many of the same stops are included, I’ve done a more abbreviated version. You’ll want to refer to the above 7 Day Itinerary for all the important information. But don’t worry! I’ve included all my pro tips for the new additions to this option, too.

Days 1-2 : Boston , with an optional day trip to Salem, Provincetown or a whale watch tour from Boston’s Harbor. Since you have the extra day, I suggest taking a day trip to one of these 3 destinations, but if you would prefer to relax and explore the city even more, you can do that, too.

Race Point Beach in Provincetown is one of the best beaches on Cape Cod.

Day 3 : Newport, RI .

Why Newport, RI Next? It’s only 1 hour and 30 minutes from Boston, and such a beautiful coastal town to visit in New England. Because of its location, it makes it easy to squeeze into a 10-day New England itinerary, too.

Here are some suggestions of awesome things to do in Newport, RI:

  • Explore Cliff Walk.
  • Tour the stunning Gilded Age mansions.
  • Have lunch at Cliff House.
  • Take this awesome morning mimosa boat tour in Newport!
  • Explore the city by trolley, which includes The Breakers mansion!

Click here to read my post on the best things to do in Newport, RI!

Castle Hill Lighthouse in Newport, RI.

Newport, RI hotel suggestions:

Splurge: The Cliffside Inn . A beautifully-decorated B&B that’s a stone’s throw from my personal favorite thing to do in Newport – the Cliff Walk.

Moderate: Attwater Hotel . A great location that’s walkable to Bowen’s Wharf, and has cute rooms and a free breakfast.

Day 4 : Woodstock, VT

Days 5 : White Mountains, New Hampshire

Flume Gorge in the White Mountains is one of the best stops to add to your 7 day New England road trip itinerary.

Day 6-7 : Acadia National Park & Bar Harbor

Day 8 : Boothbay Harbor, ME

Why Boothbay Harbor Next? One of my favorite little coastal towns in Maine is Boothbay Harbor because it’s loaded with charm and character, and offers so many incredible opportunities to get out onto the water with boat tours. Of all the places you can stop at on your way from Acadia to Portland, this is one of my favorites. It also has lots of options for scenic, waterfront dining.

Here are some wonderful things to do in Boothbay Harbor:

  • Take this awesome boat cruise to see seals, lighthouses and a lobster haul tour!
  • Stroll through the adorable downtown area.
  • Take in the views from the footbridge.
  • Have a delicious lobster roll at Shannon’s Unshelled.

Click here to read about even more things to do in Boothbay Harbor!

Boothbay Harbor is one of the cutest stops you can make between Portland and Acadia National Park. If you're able to squeeze it into your 7 day New England road trip itinerary, I highly recommend it!

Hotel Suggestion in Boothbay Harbor:

The Harborage Inn on the Oceanfront is my favorite place to stay in Boothbay Harbor. The location is perfect and walkable to town, but set back enough so that it’s very peaceful. If you can, splurge on Room 8 for panorama views of the water (it seriously feels like you’re floating on water).

Day 9 : Portland, ME

Day 10 : Back to Boston, making stops along the North Shore on the way.

A lternative suggestion : If you wanted to skip Woodstock, VT for this option, you could add an extra day in the White Mountains. You could also skip Woodstock and add a night in the North Shore on your drive back to Boston. For this option, I would suggest Newburyport.

Do I still think Woodstock, VT is worth the excursion? Yes! But an extra day in the White Mountains or a night in the North Shore may appeal to some of you, too. Do what fits your preferences the most.

I love Newburyport because it’s a wonderful balance between charming coastal town and historic shopping village. It pretty has much something for everyone, including a beautiful waterfront park, the nearby Plum Island for beaches and nature trails, and some of the best shopping in New England. For this particular itinerary, I think it’s a great option because it’s also the furthest north, and will break up your trip nicely.

Newburyport is an awesome place to add to your 7 day New England road trip itinerary. This is Market Square in downtown.

Here are some fun things to do in Newburyport:

  • Induldge in some retail therapy in Market Square and Tannery Marketplace.
  • Walk the path in the Waterfront Park.
  • Explore Maudslay State Park .
  • Drive to Plum Island to see the beaches and the nature trails at Parker River National Wildlife Refuge.

Newburyport hotel suggestion:

Compass Rose Inn is the best place to stay in Newburyport and feels like a big, warm hug when you arrive. In a beautiful and historic home, and each room is a suite with a fireplace. It’s also walkable to town, and a complimentary breakfast is included.

5 Day New England Road Trip Itinerary

Don’t have 7 or 10 days for a New England road trip? No problem! Having put a lot of thought into the best 5 Day New England itinerary, you can easily make this a jam-packed road trip style trip, or a more relaxing getaway that allows you additional time at each destination, but doesn’t get to as many places. Not sure which is right for you? I’ve outlined both to help you decide.

As before, refer to the first 7 Day New England road trip itinerary option for more detailed information on each destination.

These views can be found along Ocean Path in Acadia National Park.

5 Day Road Trip Itinerary From Boston

Day 1 : Boston

Day 2 : The White Mountains, New Hampshire

Day 3-4 : Acadia National Par k

Day 5 : Drive back to Boston , stopping at the Portland Lighthouses, and 1-2 towns along the North Shore region on your way.

5 Day Relaxed Itinerary From Boston

Days 1-2 : Boston. Two days will allow you to settle in and enjoy a more relaxed pace.

Pro Tip : If you’re not flying into Boston (ie, you’re driving in), you don’t have to stay right in Boston. You can definitely stay in a cute nearby town like Salem or Gloucester, and then take a day trip to Boston for a more relaxing getaway.

Days 3-4 : Newport, RI & Mystic, CT. From Newport, Mystic, CT is only about a 1-hour drive, which makes this an easy and relaxing afternoon excursion that’s stress-free.

Click here to read my post on the best things to do in Mystic!

Day 5 : Back to Boston, with stops in either Plymouth and Scituate on the way back (or both!). These two towns are south of Boston, and more convenient to visit when driving from Newport. I love them both, and they offer lots of charm, shopping, dining and beautiful sites to see. Of the two, Scituate is smaller with fewer things to do, but very beautiful.

Alternative suggestion 1 : Stay right in Boston for all 5 days, and take day trips! Since Boston is in such a great area, it’s very easy to get around. And as mentioned before, you can take a ferry to Provincetown on Cape Cod, or over to Salem, and you won’t need a car for either of these two excursions.

Alternative suggestion 2 : Stay in Boston for 2-3 nights, and spend 2-3 nights on Cape Cod with a day trip to one of the islands (Nantucket or Martha’s Vineyard). This option will be very coastal, and provides you with some of the best beaches and coastal towns in Massachusetts.

Nantucket is a great option for a day trip from Cape Cod if you're short on time and don't want to do too much driving.

Here are some posts that may help you if you like this option:

  • Best Towns To Stay In On Cape Cod
  • Best Things To Do In Provincetown, MA
  • Cape Cod Day Trip Guide
  • Martha’s Vineyard Day Trip Guide
  • Nantucket Day Trip Guide
  • Is Nantucket Or Martha’s Vineyard Better For A Day Trip?
  • How To See Martha’s Vineyard Without A Car

Alternative suggestion 3 : Stay in Boston for 2 nights, and then drive to the North Shore for 2 nights, and then maybe Portland for 1 night. Just north of Boston, the North Shore region includes Salem, Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Essex and Newburyport. All of these towns are pretty close to another another, and it would be easy to pick one to stay in, and take afternoon trips to the others.

Marblehead is another awesome town to add to your 7 day New England road trip itinerary.

Portland is also within 1 hour and 30 minute at the most from these towns, making it easy to pop over for the day, or a night.

Best Way To Get Around New England

The best way to see New England is definitely by car. If you fly in, I suggest renting a car from the airport to begin your road trip. If you plan to spend a day or two in Boston before beginning the road trip, I would say to hold off on renting your car until you’re ready to leave Boston.

Boston has an awesome public transit system, and Uber and Lyft are readily available, so a car will be more of a hassle to park in the city.

What To Pack For A New England Road Trip

This will, of course, depend on entirely on the time of year you visit, as New England is a four-season climate. I always suggest checking the weather reports a few days before leaving to get a more accurate idea of what the weather and temperatures will be like.

Flume Gorge in the White Mountains is one of the best things to see on a New England vacation.

I love to remind people that New England can be moody and change frequently – even in the summer, you could have chilly days, and in the winter, you might experience a warm day. Although, generally speaking, you’ll find it’s pretty much what you would expect of a four-season climate: A wet and rainy spring, a warm or hot summer, a chilly fall and cold winter.

Here are a few suggestions and tips on packing for a New England road trip that you not have thought of:

  • A reusable water bottle to reduce single-use plastic.
  • Dramamine if you plan to do any boat tours, and you’re prone to seasickness.
  • Day pack for essentials like your water bottle, camera, sunscreen, etc.
  • Comfortable shoes for exploring towns. Keep in mind that places like Boston, Nantucket, and historic small towns often have uneven cobblestone or brick streets.
  • Hiking boots if you plan on doing any hikes.
  • In general, plan to keep your clothes fairly casual. New England can be fancy if you plan a special dinner out, but is overall pretty casual. Take a look at your specific plans and eliminate any extra fancy outfits that you likely won’t need.
  • Light jackets or sweaters for mornings and evenings (even in the summer!).
  • Waterproof jacket and boots if you plan to visit in the spring or fall.
  • Don’t forget your camera! You may also want to consider an iPhone tripod with a remote shutter to elevate your travel photos from selfies to wall-worthy shots. This one on Amazon is inexpensive and perfect for the average traveler!

New England Road Trip FAQ

Is new england easy to drive around.

Very! Of course, you’ll experience traffic when you’re close to, or in, a city like Boston or Portland, ME. In that case, it’s just like driving in any other city. But overall, New England is very easy to drive around.

One thing I like to remind people is that in the more rural places, you will likely drive on a lot of dirt roads, so just be careful of any pot holes.

Is It Safe To Take A Winter New England Road Trip?

Yes! As long as you’re comfortable driving in the snow, you’ll be totally fine. Chances are, if you’re visiting in the winter, you’re excited to check out places like New Hampshire or Vermont, and those two states are among the top 3 snowiest in the whole country. So, just know that you will experience snow, and you’ll definitely be driving in it.

I always recommend that you rent a car with either snow tires or 4W Drive if you plan a winter trip. But generally speaking, most places are great at plowing roads, so unless you happen to visit during one of our big nor’easter storms, driving is easy. Just practice normal precautions.

Click here to read my post on the best winter getaways in New England!

Is Cell Service Reliable All Over New England?

Yes and no, and it depends on where you’re going. For the most part, cell service is completely reliable, and Google Maps will be able to take you everywhere.

One of the most iconic view in Acadia National Park is Jordan Pond.

However, in more remote places, again like in Vermont or New Hampshire, or even along the coast at some lighthouses or in Acadia, you will lose cell service more than you think for living in 2022 or later! I highly recommend off-lining maps for your entire route just to be safe. I can’t tell you how many times I’ve lost service while driving in VT and NH and didn’t offline maps, only to very much regret it in the moment!

Why Is Connecticut Not Part Of Your Itineraries?

I love Connecticut! But the hard thing about Connecticut is its location. It’s so far Southwest, in the exact opposite direction of Acadia National Park and most of the top destinations to visit. And since Acadia is one of the most amazing New England locations that everyone should see when they visit, I had to exclude Connecticut from the itinerary options only for the sake of time because I think Acadia offers much higher payoff for your driving time.

That’s why I was only able to squeeze in a quick afternoon trip to Mystic, CT in the 5-day option.

What About A Fall Foliage Road Trip?

I’ve got you covered! I have an entire post on the perfect New England fall road trip , which is one I’ve perfected over many years. This road trip makes stops in similar places, but has more of a focus on the best places for foliage.

You May Also Enjoy Reading:

  • Best Things To Do In New England
  • Best Time To Visit New England
  • Incredible New England Resorts & Spas
  • Best Boston Hotels Near The Aquarium
  • Awesome New England Gifts & Things To Buy During Your Visit
  • Best Christmas Towns in New England
  • Best New England Day Trips
  • Best Food Tours In Boston
  • Summer In New England: Best Places To Go & Things To Do!
  • Best Beach Towns In New England
  • Things To Do In Boston In The Fall
  • Gorgeous New England Islands Worth Visiting
  • My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary

That’s A Wrap On The Best 7 Day New England Road Trip Itinerary

Hopefully you’re now feeling ready to tackle planning your own adventure with this 7 Day New England Road Trip Itinerary! Even with 7 days, you can see so much of this gorgeous region and really cover a lot of ground. And, of course, if you have time to follow along on my 10 Day New England Road Trip Itinerary, that’s even better. But regardless of what you have time for, New England is always a good idea, and is always worth making time for. Happy planning!

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Flume Covered Bridge in Franconia is one of the best things to see in fall in New Hampshire.

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winter road trips in new england

NEW ENGLAND WINTER ROAD TRIP

Take a trip to New England for access to one of the planet’s most highly saturated skiing and riding areas —including six Ikon Pass destinations all within five hours of each other. Here’s an inside look at the northeast’s most iconic alpine adventures.

Skier making tracks on a downhill run.

Welcome to Southern Vermont’s Stratton —“The Birthplace of Snowboarding.” Start your mountain day at the Sun Bowl base area, where you’ll find easy slopeside parking, morning sun, and rolling groomers to warm up for the day. From there, cruise on up to one of Stratton’s best-kept secrets, Upper Middlebrook, which features a blend of steep pitches and winding turns that drop you off at the Shooting Star six-passenger lift or the Sun Bowl.

If it’s snowing, make sure to head to Slalom Glade—a steep, off-the-beaten path run with deep powder stashes. Need a quick pick-me-up between runs? Stop in to the Fire Tower Restaurant & Tavern in Stratton Village to enjoy one of their famous “Bacon Old-Fashioned” cocktails, complete with bacon-infused Maker’s Mark and Vermont Maple Liqueur.

After making your turns for the day, experience the mountain at night on a Full Moon Snowshoe Tour , which will take you through the rolling New England landscape and end with a cozy campfire, hot cocoa, and a new perspective of Stratton's starlit skies.

Killington Resort

Aerial View of Killington Resort

Drive an hour north, and you’ll be ready to snap in again at Killington —“The Beast of the East,” which also boasts New England’s longest season. While there, learn to ski bumps with Olympic Gold Medalist and world champion mogul skier, Donna Weinbrecht. She teaches mogul camps on the mountain year-round—many of which are lady-skier exclusive.

Killington is home to the Audi FIS World Cup—don’t miss trying your hand at their most iconic run, Superstar, the official World Cup race trail. Also, be sure to make your way to the top of Killington Peak—Vermont’s second-tallest peak—to snap an unforgettable selfie.

After making your turns, treat yourself to dinner at the Ledgewood Yurt , an exceptional, authentically Killington experience all in its own. To get there, take a snowcat-drawn sleigh ride to a remote trailside location for a five-course meal and a social dining atmosphere—the perfect finish to a day on the New England snow.

Sugarbush Resort

winter road trips in new england

Snow report says powder? Start your day off with Sugarbush Resort's first-tracks cat skiing aboard the Lincoln Limo—a specialty snowcat fitted with 12-passenger cabin, flat screen, and cushy seats. First Tracks tours leave from the base of Lincoln Peak and venture to the top of the North Lynx Triple for early bird access to pristine, deep powder and untouched corduroy.

Spend the afternoon on Sugarbush Resort’s luxurious Lincoln Peak, and then take the high-speed Slide Brook Express over to the second base area, Mt. Ellen, for throwback skiing at its finest. On the way, you’ll glide over the Slide Brook Basin’s 2,000 wooded acres of incredible off-piste terrain.

For après, stop by the Castlerock Pub at the mountain’s base for live music and cold beer. Or, get fancy with classic French cuisine at Chez Henri—a mountain favorite for more than 50 years. Come sit down for a glass of red wine, some steak-frites, and cheese fondue with Henri himself, the original proprietor who is still a nightly fixture at the restaurant.

Tomorrow, take a leisurely drive from Vermont to New Hampshire as you make your way to Loon Mountain. Spend the afternoon relaxing around the resort, giving your legs a rest before hitting the slopes again.

Loon Mountain

winter road trips in new england

Get at it early on Loon Mountain’s award-winning progression of six terrain parks. Skiers and riders as young as three years old will be able to take part in some creative riding at the Paul Bunyan–themed Burton Riglet Park, the Burton Lil’ Stash, the log cabin wall ride, and the nearly-mile-long Loon Mountain Park—not to mention, New Hampshire’s only Superpipe.

Before skiing one of Loon Mountain’s most iconic black diamond runs, Upper Walking Boss, kick off your skis and ditch your board at the top of North Peak for a quick visit to the bird sanctuary—the mountain’s best-kept secret. To get there, look for the sign that at the top of Sunset Trail, and take a short walk into the woods. Make sure to stash some birdseed in your pocket for feeding, and you’re sure to have a chickadee or nuthatch eat right from your hand.

Warm up after a long day on the mountain with an atypical après—Caribbean-style rum punch at the Summit Café , a tropical downpour of rum, grenadine, and fruit juice. The kids will love riding the wood-fired steam engine on the J.E. Henry Railroad. This authentic German-built train that looks just like “The Little Engine that Could” shuttles skiers and riders between Loon Mountain’s two main base lodges every day in the wintertime.

Sunday River

winter road trips in new england

If you’re driving to Maine’s Sunday River for a day on the mountain, park at White Cap Lodge for quick access to the slopes. Its eight peaks are all interconnected, so it will be easy to get to the western peaks on powder days, which are chock full of glades and hidden pockets of snow.

If you’re up for a challenge, take on one of Sunday River’s most iconic runs—White Heat of White Cap Peak. This steep double black diamond drops straight down the fall line and is packed with moguls, a long, sustained leg-burner for even the most experienced skiers and riders. Make sure to also take a minute to make your way to the top of the Jordan Bowl for a snowy selfie that overlooks the Presidential Range.

Refuel at Peak Lodge with one of Sunday River’s world-famous sticky cinnamon buns. Drenched with creamy glaze and bigger than your face, this sweet treat pairs perfectly with a spicy Bloody Mary, complete with smoky vodka and candied bacon.

Tomorrow, treat yourself to a late wake-up call before packing your gear and making the two hour drive northeast to Sugarloaf.

winter road trips in new england

Kick off the day early at Sugarloaf , where you can experience New England’s only lift-serviced above-treeline skiing. Summit by hopping on the Timberline Quad, where you can snap a selfie with Katahdin and Mount Washington as your backdrop.

Make your way to the Snowfields for legendary runs from the mountain’s 4,237-foot summit, and don’t miss Winter’s Way—the first trail ever cut on Sugarloaf by founder, Amos Winter. When the lifts stop running at Sugarloaf, the party is just getting started. Stay on-mountain or within the free Sugarloaf Explorer shuttle route so your ski day can easily spill over into après.

No trip to the Loaf is complete without trying “New England Ski Resort’s Top Burger”: the legendary Bag Burger from The Bag & Kettle . Or try a multi-course mid-mountain tasting at Bullwinkle’s , accessible only by snowcat, where you’ll dine on chef-prepared small plates inspired by cuisines around the world.

High contrast image of a chairlift surrounded by trees.

Book Your Next Adventure

Inspired by this road trip? Ikon Pass Travel is a new travel planning service for Ikon Pass holders that helps you customize your perfect mountain getaway all in one place.

winter road trips in new england

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winter road trips in new england

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Road-Tripping New England: My Suggested Itinerary

An old lighthouse on the coast of Maine, USA

I’ve said it before and I’ll say it again: The United States is made for road trips . With its bustling cities, rugged national parks, and delicious eats, the sheer size and diversity of this country never cease to amaze me.

I’ve road-tripped the USA five times, spending a cumulative year exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.

One region in particular that I love to drive around is New England.

Having grown up in Boston and gone to college in Western Massachusetts, I’ve spent a lot of my life in this part of the country. Last summer, I spent even more time here, exploring parts of Maine , Cape Cod, and upstate New York that I had never seen before.

And yeah, I’m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.

And, given the fact the region is relatively small, it’s easy to get around, so you can cover a lot of ground in a short amount of time.

If you’re thinking of visiting, here’s a suggested road trip around New England to help you get a feel for the region:  

Days 1-3: Boston, MA

The summer skyline of Boston, Massachusetts

These are some of my favorite things to do in Boston:

  • Walk the Freedom Trail – This 2.5-mile (4km) route takes you through colonial Boston. Starting in the Boston Common and winding past Faneuil Hall, the Old State House, and Bunker Hill, this historical walk teaches you about life in colonial and revolutionary times. The tourism board also offers guided tours (tickets are $16 USD).
  • See the Museum of Fine Arts – This museum has over 450,000 pieces of fine art, from the pre-Columbian era to Italian Impressionism. It’s one of the best collections in the country. Admission is $27 USD.
  • Visit Bunker Hill Monument – The Battle of Bunker Hill in 1775 was one of the first major clashes of the Revolutionary War. While the redcoats won, the Americans wore British forces down more than was expected. The monument stands 221 feet tall; you can climb to the top to enjoy the view (it’s the best view of Boston). (Temporarily closed for restoration work).
  • Lounge in Boston Common – This is the oldest city park in the US, dating to 1634. It was once used as communal pastureland by Puritan settlers (they also executed some “witches” here as well). Today, it’s a great place to relax, people-watch, and picnic.
  • Visit Harvard – Harvard University is the first and oldest university in the country (founded in 1636, far predating the United States). The campus offers free one-hour tours through the grounds and buildings. Afterward, grab a coffee and people-watch in the alternative and artsy Harvard Square.
  • Catch a game at Fenway Park – This is one of the oldest baseball parks in the country (it opened in 1912). Bostonians are die-hard Sox fans, so even if you don’t like baseball, go for the cultural experience. Tickets start around $20 USD for standing room or bleacher seats, and $31 USD for the grandstand. Guided tours of the stadium are offered year-round as well. There are various tour options, but the standard guided tour lasts 90 minutes and costs $25 USD per person.

For more suggestions on what to do in the city (and there’s plenty), check out my free guide to Boston .

Where to Stay

  • HI Boston – This is my favorite hostel in the city. It’s clean, spacious, and social, and the staff are super friendly and helpful.

For more suggestions, here is my list of the best places to stay in Boston .  

Days 4-5: Portland, ME

An iconic lighthouse in Portland, Maine, USA

  • Visit Peaks Island – This small island is home to around a thousand people. Located just 20 minutes off the coast, it’s a laid-back place to eat, lounge, and check out the quaint shops. There’s also a small World War II museum here, as well as a neat umbrella cover museum (it’s more interesting than it sounds!).
  • Try a Holy Donut – Holy Donuts are made from Maine potatoes (which sounds weird, but they are incredibly tasty), so they are at least somewhat healthier than your standard donut. There’s always a line, so try to get there early!
  • See the lighthouses – There are several historic lighthouses worth seeing nearby, including the Portland Breakwater (which was designed to look like a Greek monument), Spring Point Ledge (which was built in 1897 and is open for tours on weekends), and Portland Head Light (which was built in 1791).
  • Wander Victoria Mansion – This ornate mansion-turned-museum, built in 1860 and declared a National Historic Landmark in 1971, boasts a brownstone exterior and elaborate interior furnishings. It’s incredibly lavish, shedding light on what life was like for the well-to-do in the late 19th century. Admission is $16 USD.

While you’re in Portland, be sure to check out some of the city’s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.

  • Black Elephant Hostel – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping.

Days 6-8: Bar Harbor, ME

Bright blue skies in Acadia National Park in Maine

Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.

Here are some things to see and do in and near Bar Harbor:

  • Explore Acadia National Park – This gorgeous national park encompasses forests, lakes, and mountains, and covers a large swath of the Atlantic coastline. It’s incredibly popular in the summer for hiking, biking, camping, kayaking, and more. You could easily spend a couple of days just exploring the park. A 7-day vehicle pass is $30 USD and camping starts at $22 USD per night.
  • Visit Abbe Museum – This museum showcases the area’s indigenous history and culture. It’s very informative and sheds important light on a history often overlooked. It’s part of the Smithsonian, so you know it’s going to be good! Admission is $10 USD.

Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie’s (delicious food all around).

  • Bar Harbor Manor – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace.

Day 9: Bangor, ME

The exterior of Stephen King's house in Maine

My favorite places to eat are the Fiddlehead (delicious food all around) and Judy’s (best diner breakfast). For a drink, head to Mason’s Brewing.

Where to Stay Bangor is a small town, so you’ll want to compare prices on Booking.com and Airbnb to see what best suits your budget.  

Days 10-12: Moosehead Lake, ME

The calm waters of Moosehead Lake in Maine, USA

Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer.

For dinner or drinks, head to the Stress Free Moose Pub in Greenville.

  • Leisure Life – This accommodation is basic, but it’s in a great location (in Greenville), and the staff are super helpful.

Days 13-14: Mount Washington, NH

Mount Washington, New Hampshire as seen from the distance at sunset

Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).

Where to Stay You can stay in nearby Gorham or Littleton. Check Booking.com and Airbnb to see what best suits your budget.  

Days 15-17: Burlington, VT

The skyline of Burlington, Vermont as seen from over the lake

Some of my favorite things to do here are the following:

  • Wander Church Street – This pedestrian-only thoroughfare is the heart of the city. Café-hop, browse the bookstores and other shops, and take in the slow pace of life.
  • Get out on the water – Spend some time out on the water and soak up the sun. Boat rentals, cruises, paddle boarding, kayaking — you can do it all here. There are also several beaches you can lounge on, with North Beach being the most popular.
  • Visit Ben & Jerry’s – This is where the global ice cream brand originated. If you have more time, you can visit the nearby factory in Waterbury and see the “ice cream graveyard,” where Ben & Jerry’s commemorates its obsolete flavors.
  • Indulge in craft beer – Burlington is a craft beer mecca, home to over a dozen breweries. Go bar- or brewery-hopping to taste the best the city has to offer. Local favorites include Foam Brewers, Zero Gravity, Fiddlehead Brewing Company, and the Burlington Beer Company.

Where to Stay There are no hostels here, so compare prices on Booking.com and Airbnb to see what best suits your budget.  

Days 18-19: Green Mountain National Forest, VT

A solo traveler hiking in the Green Mountain National Forest

Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.

Since it’s a national forest, camping here is free (unless signs advise otherwise).  

Days 20-22: The Berkshires, MA

An old hiking sign in the forest near Mount Greylock in The Berkshires

Here are some things to see and do:

  • Hike Mount Greylock – Standing 3,491 feet tall and located in a state park encompassing over 12,000 acres, Mount Greylock is the highest peak in Massachusetts. There are several trails that lead to the summit (including a portion of the Appalachian Trail). The hike takes around 90 minutes, and the views from the top are absolutely breathtaking — you can see for miles!
  • Visit the Norman Rockwell Museum – Norman Rockwell, the prolific American painter and illustrator, spent much of his life in Stockbridge. A museum was established there to showcase his life and works, highlighting the evolution and impact of his art. Admission is $20 USD.
  • Explore Natural Bridge State Park – Located in North Adams, this park is home to a natural bridge of white marble (which is over 550 million years old) as well as an old marble quarry. There’s an easy trail around the bridge and quarry, and plenty of relaxing fields and meadows to picnic in. Parking is $20 USD for out-of-state residents.

Day 23: Amherst, MA

An aerial view of the UMass campus in Amherst, Massachusetts

Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson’s life. There are often events and poetry readings here, so check the website to see what’s on during your visit. Guided tours last 60 minutes and cost $15 USD. Currently closed for restoration work.

As for food, Antonio’s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I’m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.

Day 24: Back to Boston

It’s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston!  

Bonus Destination: Cape Cod, MA

A purple sunset on the beaches of Cape Cod, USA

Here are some things to see and do during your stay:

  • Go whale watching – From April to October, you can see finback, minke, and humpback whales, as well as dolphins and seals. Tours cost around $67 USD.
  • Hike or bike the National Seashore – Created in 1961 by JFK, this park spans over 43,000 acres. There are 11 hiking trails, as well as half a dozen cycling trials. All of them are well marked so it’s an easy way to stretch your legs and take in the beautiful landscape.
  • Visit some lighthouses – There are dozens of picturesque lighthouses around Cape Cod, some of which are open to the public. Don’t miss Nauset, Nobska, and Highland lighthouses.

New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I’m proud to have grown up in this region and encourage you to explore my backyard!

Book Your Trip to the United States: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe, so you always know no stone is being left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as it has the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it, as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

  • Safety Wing (for everyone below 70)
  • Insure My Trip (for those 70 and over)
  • Medjet (for additional repatriation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road, and I’m sure they will do the same for you.

Need an Affordable RV for Your Road Trip? RVshare lets you rent RVs from private individuals all around the country, saving you tons of money in the process. It’s like Airbnb for RVs.

Want More Information on the United States? Be sure to visit our robust destination guide on the USA for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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New England Winter Road Trip

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Last winter, the girls and I embarked on a New England winter road trip. We spent 9 days traveling through the New England states exploring all the fun winter activities. Our itinerary changed a couple times due to weather, but overall we had a fantastic vacation.

New England is a great road trip destination, since the states are so compact and close together. Plus during the winter, the roads are not scary like other parts of the US that get snow.

Day 1 of our New England Winter Road Trip:

We flew into Boston and was supposed to arrive around 11am, but unfortunately we had a flight delay. After arriving around 4:00, it took over an hour to get our car rental. We eventually got on the road to head to Portsmouth close to 5:30 pm.

With all the delays, we had no time to wander around Portsmouth before dark. Our original plan was to have a late lunch in Portsmouth, stroll around the historic downtown area, explore a nearby beach and then dinner.

At this point, we were exhausted. We grabbed fast food for dinner, checked into our hotel and called it a night. Not exactly a great start to the trip, but sometimes travel days are like this.

We stayed at Wentworth by the Sea, a Marriott hotel. It’s technically in New Castle, but very close to Portsmouth. Absolutely loved it! It is a charming historic hotel right on the ocean.

Wentworth by the Sea Hotel

Day 2- Portland, Maine

We woke up early and started our drive to Portland. It was only an hour away, so we didn’t have far to travel.

We spent the morning exploring all the lighthouses around the Portland area. This is such a beautiful area and the snow really adds to the charm. Although, I’m sure they are just as beautiful in the summer too!

Portland Headlight was the prettiest lighthouse we saw in my opinion. Spring Point Ledge Light was the most adventurous one! We walked over icy rocks to get to it. The last one we saw was Portland Breakwater lighthouse. There was too much snow and ice, so we didn’t walk up to this one.

Portland Head Lighthouse

For lunch, we ate at Flatbread Company. The pizza was delish, and the view even better! It’s right on the water. For dessert, we tried the Whoopie Pie. Apparently its a thing in Maine. It’s made of chocolate, so of course I loved it.

After lunch, we walked along the East End Beach. First time I’ve ever seen snow and ice on a beach! I wanted to visit the Eastern Cemetery but it was covered in snow and we were cold, so we skipped it.

East End Beach in New England Winter Road Trip

Our hotel for the night was located near Old Port, so we checked in early to ditch the car and walk around. Old Port was adorable! I love historic areas and this is one of the best! Cobblestone streets, charming shops, great restaurants and just steps away from the piers. We spent the rest of the afternoon exploring the area.

For dinner, we walked down to the pier and ate at Luke’s Lobster. When in Maine, lobster is a MUST! The grilled cheese lobster was pure yumminess. And again the views here are great!

For us Texans, we called it a night because it was COLD! We stayed at the Aloft hotel and the location was perfect! Walking distance to many shops and restaurants. They have a fun lounge and bar area that’s great to hang out in.

Day 3 of our New England Winter Road Trip

This was one of the days I was looking forward to the most, but I had to change plans last minute due to a snow storm coming in the next day.

Originally, We were going to drive to Jackson, New Hampshire and see snow sculptures from the snow sculpting competition, then head to Nestlenook Farms for ice skating. After, drive to North Conway where we would stay the night, hike to Diana’s Bath (A frozen waterfall), explore the downtown area and have dinner. The next day would include driving the Kancamagus Highway and seeing the Ice Castles in Woodstock, NH, then heading on to Burlington, VT. The Ice Castles are on my bucket list! But it did not happen this trip, so I’ll have to go back.

Kancamagus Highway

Instead, we drove to North Conway and explored the area for an hour or so. Then we drove the Kancamagus Highway. I’ve driven this in summer and its beautiful, but the snow makes it look like a winter wonderland!

After that, we drove straight to Burlington, VT. Checked into our hotel and had a pizza delivered from Big Daddy’s.

Big Daddy's Pizza

Day 4- Burlington, VT

We were ready to explore Burlington today! This is such a cute town, we couldn’t wait to see it. Our hotel was close to everything, so I didn’t have to worry about driving.

For a late breakfast, we ate at The Skinny Pancake. The blueberry crepes were amazing! Afterwards, we walked along Lake Champlain. There are great walking trails in Waterfront Park, although some of them were covered in snow and ice. We took a small break at the hotel to warm up a bit.

Church Stret

Our next destination was Church Street. Church Street is picture perfect! Like right our of a postcard! We explored several boutiques, coffee shops and bookstores. It was getting colder and started snowing, so we took frequent coffee and hot chocolate breaks.

For dinner, we ate at El Cortijo Taqueria. Considering that we are from Texas and have an abundance of amazing tacos, this place was pretty good.

In the evening, Church street is covered in lights which makes it even more beautiful! We didn’t stay to long though because it was COLD! Another early night in the hotel room.

Church Street

Day 5 -Drive To Boston

Today’s plans changed as well. We were going to get an early start today to explore Stowe and go horseback riding, but the weather didn’t cooperate.

We stayed at the hotel as long as possible to wait out the snow storm, but it didn’t let up. I decided to head to Boston anyways, because I’d already booked the hotel.

The drive should have taken around 3.5 hours, but it took us 7 hours! I am from Texas and do not drive well in this weather, so I did go slow. I was keeping pace with most of the cars on the road though and I’m glad I upgraded to an SUV.

We did finally make it to Boston and stayed in the downtown area by Faneuil Hall.

Day 6- Boston

I’ve been to Boston a couple times and love it! The city is full of history, delicious food and very walkable!

Our first stop was Quincy Market. So many food options!! I tried clam chowder for the first time and liked it. It’s perfect for winter in Boston! We tried many other treats from the numerous vendors there. All good.

We walked some of the Freedom Trail, browsed through shops and explored historic cemeteries. I am fascinated by old cemeteries. There are some that have people from the Mayflower buried here! The snow covered up a bunch of the headstones, so it was hard to see the dates.

Boston

Of course, plenty of stops for coffee and hot chocolate since it was cold. We made our way to the North End area. For dinner, we stopped at La Famiglia Spagnuolo’s, because one of the employees was on the street and convinced us to come in. It’s a small Italian restaurant and we loved the atmosphere. The food was delicious as well!

Day 7- Mystic, CT

The roads were much better today, so we continued on to Mystic Connecticut. But first, we took a detour to see Louisa May Alcott’s Orchard House. The girls are fans.

Our first stop in Mystic, was the Olde Mistick Village. This is a cute shopping village with unique shops. Franklin’s General Store is perfect for souvenir shopping! They have homemade fudge, locally made jams, pickles, salsas, syrups and more. Plus candles, books, glassware and fun jigsaw puzzles.

Another favorite was Cloak and Wand. This is perfect for Harry Potter fans! It’s a wizarding shop with a potion bar. They sell magical items, books and apparel. The potion bar serves custom hot chocolates and sodas. Since they are not affiliated with Harry Potter, they do not serve butterbeer. They do have a delicious substitute! We strolled around here for a couple hours.

Mystic is the cutest city! We enjoyed just driving around and looking at the scenery. Our next stop was downtown Mystic. We explored here for a couple hours before heading to dinner. We are big Julia Roberts fans, so we had to eat at Mystic Pizza for dinner! The pizza was delicious and I loved the atmosphere.

Mystic Pizza

We stayed at the Mystic Marriott Hotel. The hotel was fantastic. Very clean and staff was great.

Day 8- Newport, RI

Before leaving Mystic, we had brunch at Rise. It’s located in the downtown area. The food was great!

Next, we headed to Newport. The number one thing I wanted to do was the Cliff Walk. The Cliff Walk is located on the coast. The views here are amazing! One side is ocean and the other side are huge mansions! Some of the mansions are open for public paid tours. It was cloudy today, but I bet sunset would be phenomenal! We did not do the entire 3.5 mile walk, but did do a good portion.

Cliff Walk in Newport

After the Cliff Walk, we checked into our hotel. Our hotel was located in downtown within walking distance to shops, restaurants and attractions.

Newport’s downtown area is charming too! More cobblestone streets, charming buildings, unique boutiques, lots of food options and on the water! We strolled through downtown for a couple of hours and explored the wharf area. Then had dinner at Gas Lamp Grille.

Day 9 on our New England Winter Road Trip

It’s our last day and I decided to add on Salem , since the girls had never been. Salem is a bit of a detour from Boston where our flight was leaving, but we had plenty of time.

For breakfast, we stopped at the cutest little diner on the way. The Little Depot Diner is a renovated train car in Peabody, MA. The food here was delicious!

Then it was on to Salem. I’ve been here before and liked it. Today, not so much. I’m not sure if it’s because it was winter or covid, but hardly anything was open. Definitely a wasted trip.

Then it was on to the airport to fly home 🙁

Overall, we had a fabulous time on our New England winter road trip. I enjoyed exploring the area and hanging out with my girls. We do not have a true winter in Dallas, so being in real snow was incredible. The New England area is fairly easy to navigate even in snow storms. I did not have to deal with snow chains or steep mountain roads.

There are things that I still need to do, so I’ll be back for more winter fun. And summer fun. And fall fun 🙂

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12 Day New England Road Trip Itinerary

Kara Last updated: February 3, 2024 United States 8 Comments

New England Road Trip

Embark on an exciting New England road trip, exploring Cape Cod’s beaches, Maine’s coastal beauty, and the vast White Mountains of New Hampshire. This fast-paced itinerary is perfect for outdoor enthusiasts, offering a mix of sightseeing, town hopping, and hiking. Each destination has its unique charm, providing a well-rounded experience of the best sights in the American Northeast.

Table of Contents

About this New England Road Trip Itinerary

I did a similar version of this road trip with my very good friend, Jocelyn. We were just 18 years old and this was our first solo trip without parents.

Jocelyn and I loved each of the locations on this trip and enjoyed the ever-changing scenery. It was the first road trip we had ever planned, so there were many learning experiences to come from this.

The biggest challenge we had was fitting three states into a 10-day itinerary. While it was manageable, our days were long and allowed only a glimpse of each place. In this revised itinerary, we allocated an additional day on Cape Cod and in Portland so you can truly enjoy these locations. We also added optional day trips to allow you to customize the itinerary based on your preferences.

This itinerary necessitates a car. Be prepared for frequent driving, spanning a few hours almost every day.

This itinerary does not include Boston or the main section of Acadia National Park , though you can easily add these locations onto this itinerary if you have more time.

Drive to Stonington, ME | New England Road Trip Itinerary

Where You Will Stay on This New England Road Trip

Day 1-4: Cape Cod, Massachusetts Day 5-6: Portland, Maine Day 7-9: Camden, Maine Day 10-11: Lincoln, New Hampshire

What You’ll See on This New England Itinerary

  • Martha’s Vineyard
  • Provincetown

Portland, Maine

Cape Elizabeth

  • Camden, Maine
  • Isle au Haut, Acadia National Park

Kancamagus Highway

Franconia Notch State Park

New England Road Trip Itinerary: Day 1

Arrive on Cape Cod

Cape Cod is New England’s beach paradise, adorned with seaside towns, shopping districts, historical sites, and islands to explore. Many towns dot the cape, each hiding its own treasures and activities. Adding to its allure are picturesque cranberry bogs, scenic bike pathways, and iconic lighthouses. Just off the Cape’s shores lie the enchanting islands of Martha’s Vineyard and Nantucket.

On this itinerary, you will spend four days on Cape Cod , visiting Martha’s Vineyard, Provincetown, and other highlights in the area. On the first day of this itinerary, drive or fly to Cape Cod. If you’re coming from a distance, consider flying into Boston and renting a car from there.

Where to Stay on Cape Cod

Cape Cod is filled with idyllic beach towns to reside in. For convenient access around the island, it’s recommended to stay in a centrally located town. Some of the best options include Chatham, Hyannis, and Harwich. These towns all have plenty of shops and restaurants to visit, beautiful town beaches, and nearby activities.

During our trip, we stayed in Falmouth for its ease of access to Martha’s Vineyard. Its downside is its distance from Provincetown, the National Seashore, and other communities. But Falmouth itself is a scenic small town with many great restaurants and homey beach vibes. We loved our stay here.

Falmouth | New England Road Trip Itinerary

Falmouth Main Street

Here are some hotel recommendations for a stay in Falmouth:

There are a few InnSeason Resorts buildings around the Falmouth area. We stayed in the InnSeason Resorts Captain’s Quarters and greatly enjoyed our stay. The rooms were spacious with a large king-sized bedroom, two bathrooms, kitchen area, living room, and patio. This resort was right across the street from a white sand beach and was only a mile walk from the Main Street.

Falmouth InnSeason Resorts | New England Road Trip Itinerary

InnSeason Resorts Harborwalk is in an even better location, as it is only a half mile from Falmouth Main Street and is 5 minutes from the Island Queen Ferry. You will not get immediate beach access from this site, but you overlook a picturesque harbor.

InnSeason Resorts Surfside is 2 miles from the Falmouth main town, making walking here difficult (be mindful that parking in Falmouth can be a challenge). For this reason, I do not recommend this resort, however you do get beautiful ocean views.

Inn on the Sound  is another great place to stay in Falmouth featuring private beach access and rooms with an ocean view. The Inn provides an array of activities including tennis courts and horseback riding, and they serve a delicious breakfast each morning. The Inn is also in a great location, being only a mile from the Falmouth Main Street.

Note: Boston is another fantastic destination for a New England road trip. Discover more about things to do in our Guide to Boston. If you prefer to stay in Boston rather than on Cape Cod, you can still take a day trip to Provincetown to experience a Cape Cod highlight.

New England Road Trip Itinerary: Day 2

Cape Cod – Martha’s Vineyard

Martha’s Vineyard, a sizable island off the Cape Cod coast, boasts a variety of attractions including coastal towns, shopping districts, beautiful beaches, and picturesque clay cliffs. During our day trip here, we explored the island’s highlights: the delightful Oak Bluffs town, the lively Edgartown , and the serene coastal beauty of Aquinnah. These three locations captured the essence of Martha’s Vineyard, providing us with a fulfilling and enjoyable day.

Oak Bluffs | New England Road Trip Itinerary

For a full day guide, read our One Day in Martha’s Vineyard itinerary (coming soon).

What About Nantucket? Nantucket is another day trip destination from Cape Cod. We chose Martha’s Vineyard for its drivability, the allure of its red cliffs, and for the various towns to visit. But Nantucket holds its own treasures, with popular beaches, biking trails, and a fashionable shopping town. If you wish to travel to Nantucket, Hyannis town offers ferries to and from the island.

New England Road Trip Itinerary: Day 3

Cape Cod – Provincetown

Time on the road: (From Falmouth) 4 hours to and from Provincetown.

A trip to Cape Cod would be incomplete without seeing Provincetown. This lively town is brimming with shops, antique stores, art galleries, ice cream stands, restaurants, and it’s well-known for its welcoming LGBTQ+ community. The streets are bustling with a mix of people, cars, and bikers.

We spent the day shopping along Commercial Street, climbing to the top of Pilgrim Monument, and strolling along the pier. Set aside 4 hours minimum to explore the town, but you could easily spend a full day here.

Provincetown | New England Road Trip Itinerary

Surrounding Provincetown are several National Seashore beaches, three lighthouses, and a multitude of bike trails.

We went to Race Point Beach which sits on Cape Cod’s northernmost tip. The beach is good for sunbathing but not so much for swimming. Even in late July, the water was still very cold. Another thing to keep in mind about swimming is the wildlife nearby. We came across a large herd of seals sunbathing and swimming near the entrance to Race Point Beach. They were a joy to watch, but I wouldn’t want to run into them in the water.

Race Point Beach

We had heard about Race Point Lighthouse and figured it was a popular spot to visit. We decided to walk there from Race Point Beach, thinking it would be a touristy thing to do. However, we realized it’s actually a 4-mile round-trip hike to get there. After an hour of not seeing anyone else making the same walk, we decided to turn back. I do not recommend making this trip. From our experience, we recommend focusing your time on seeing Provincetown, and only making it to the beach if you have plenty of time to spare.

For more information about our Provincetown experience read our article, One Day in Provincetown (coming soon).

New England Road Trip Itinerary: Day 4

For your last day on Cape Cod take your pick of where you want to go. The Cape is dotted with historic towns, bike pathways, pristine beaches, and cranberry bogs to explore!

Cape Cod Rail Trail. If you love to bike, I recommend taking on the Cape Cod Rail Trail. It is a 27-mile bike path that runs through six Cape Cod towns, passing by ponds, salt marshes, and Nickerson State Park. It’s named after the old railroad system that used to operate along this route. While the trail itself doesn’t offer a lot of coastal views, you can easily veer off to reach coastal areas and National Seashore beaches. You’ll find bike rentals and parking options conveniently located along the path, allowing you to start at different points. Find more information about the Rail Trail and map here.

Cape Cod Rail Trail | New England Road Trip Itinerary

Cape Cod Rail Trail | Jim Bogosian/shutterstock.com

Visit Chatham. Nestled on the Cape’s shoreline, Chatham stands out as one of the most scenic towns, celebrated for its charming shopping avenues and maritime heritage. Nestled between waters on three sides, this place thrives as a hub for nature trails, biking routes, golfing, kayaking, fishing, and stunning beaches. Don’t miss the chance to explore Chatham Light and Stage Harbor Light, two captivating spots that enhance the town’s allure.

Chatham, MA | New England Road Trip Itinerary

Chatham | Exploring and Living/shutterstock.com

Visit Sandwich. Founded in 1637, Sandwich proudly holds the title of the oldest town on Cape Cod, rich with historical significance. Exploring Sandwich is a treat, with its historic streets, the intriguing Glass Museum, and the impressive Heritage Museums & Gardens. The town is also a haven for nature enthusiasts, offering expansive marshes, dunes, woodlands, a picturesque boardwalk, and access to the bay.

Spend the Day in Falmouth. Falmouth is a fantastic place to spend a restful day enjoying Cape Cod’s peaceful ocean atmosphere. Start your morning biking along the Shining Sea Bikeway, a 10.7-mile rail trail that runs from North Falmouth to Woods Hole. The leisurely takes you past marshes, seaside views, and cranberry bogs. After cycling down the peninsula, spend the afternoon in Woods End, a tiny fishing village with a few shops, restaurants, and a delightful bakery. Nearby, you can bike to the historic Nobska Lighthouse, or head over to Nobska Beach – a popular swimming spot.

Woods Hole, MA

New England Road Trip Itinerary: Day 5

Drive to Cape Elizabeth and Portland

Time on the road: (From Falmouth) 5 hours

Devote a day to drive to Portland, Maine. This drive takes about 5 hours in total, but you can add stops at coastal towns along the way. Either begin the drive early to ensure ample time to explore Cape Elizabeth and Portland, or take a leisurely drive and reserve Cape Elizabeth for the following day.

Note: If you want to add more time onto this trip, you could easily add on a day (or multiple days) in Boston. Learn more in our Guide to Boston.

Kennebunkport

Along the way to Cape Elizabeth, we stopped in Kennebunkport, a small coastal town on the southern end of Maine. Here visitors will find cute shops, a few restaurants, a very popular Clam Shack, and paddle boarding/ kayaking activities. Kennebunkport is a good stop if you want to shop or stretch your legs, but otherwise we were not impressed. It was difficult to find parking, we were eager to make it to Cape Elizabeth, and there was little here to see.

Kennebunkport | New England Road Trip Itinerary

Note: Rather than stopping in Kennebunkport, consider stopping in Portsmouth, New Hampshire. This larger maritime town has more to see and do, from a rich history, delicious restaurants, and boutique stores to shop in.

After a lengthy drive, you have arrived at Cape Elizabeth. Despite its relatively small size, this Cape is brimming with lighthouses and historical significance dating back to the American Revolutionary War. If you have energy, stop by Fort Williams State Park to see Maine’s iconic Portland Head Light. Or, if you are exhausted from the drive, save Cape Elizabeth for tomorrow and continue to Portland (which sits just above the Cape).

Portland Headlight | New England Road Trip Itinerary

Portland Head Light

The top sight in Cape Elizabeth is Fort Williams State Park, home to the iconic Portland Head Light. That is Maine’s oldest and most visited lighthouse. Short walking trails surround the Portland Head Light to see it from all angles. Daring visitors can also walk out onto rocks that lie just across the water from the lighthouse for another great view. Fort Williams State Park is open from April to mid-November from sunrise to sunset. Parking at Portland Head Light is $2 per hour and $10 per day for all non-residents.

Other places to visit in Cape Elizabeth include:

  • Portland Breakwater Light (Bug Light)
  • Crescent Beach State Park
  • Two Lights State Park

Crescent Beach State Park

Crescent Beach State Park | Alexey Stiop/shutterstock.com

Where to Eat on Cape Elizabeth

The Lobster Shack at Two Lights. This isolated lobster shack sits right along the rocky shoreline, providing sweeping views of the blue coast. The Lobster Shack at Two Lights is always bustling with friendly locals and travelers enjoying fresh lobster rolls and seafood delicacies.

winter road trips in new england

A Bite Into Maine. This critically acclaimed food truck is located inside Fort Williams State Park. They serve lobster rolls, chowder, and lobster grilled cheeses. Their lobster rolls hold critical acclaim from The Food Network, Food & Wine, and USA Today.

Find more things to do in our Guide to Cape Elizabeth.

By the time you reach Portland, chances are you’ll be exhausted. We recommend checking into your hotel and then treating yourself to a nice dinner to unwind.

Portland

Where to Eat in Portland

Portland is a foodie’s haven, where every block has another great restaurant to try. This makes narrowing down a list of where to eat difficult. Based on what I have gathered from TripAdvisor and travel bloggers, these are some of Portland’s top-rated restaurants.

Top seafood restaurants in Portland include:

  • DeMillo’s On the Water
  • Luke’s Lobster Portland Pier
  • Portland Lobster Company
  • Highroller Lobster Company

Portland DeMillo's On the Water

DeMillo’s On The Water

Some other great restaurants to check out include:

  • Fore Street
  • Evo Kitchen + Bar
  • Solo Italiano

Where to Stay

Courtyard by Marriott Portland Downtown/Waterfront

Situated right in the heart of downtown Portland, this hotel is conveniently close to many restaurants, shops, cafes, and the Old Port area. Its central location was a great advantage as we could easily explore the city on foot, without concerns about parking, taxis, or safety. The hotel staff was welcoming, and the rooms were tidy and cozy. Our experience staying here was highly enjoyable, and we felt that paying a bit more for the excellent location was definitely worthwhile.

Portland Courtyard Marriott

Other great hotel locations in downtown Portland include:

  • The Press Hotel, Autograph Collection
  • Canopy by Hilton Portland Waterfront
  • The Docent’s Collection
  • The Chadwick Bed and Breakfast
  • Hampton Inn Portland Downtown – Waterfront
  • Portland Harbor Hotel

Inn By the Sea

Just a short distance from Crescent Beach State Park, at the southern edge of Cape Elizabeth, you’ll find Inn By the Sea , a high-end oceanfront resort. It’s a perfect choice for anyone seeking a tranquil vacation escape. The resort provides a variety of rooms, including beach suites, multi-bedroom options, and single-bedroom accommodations. Additionally, the resort offers convenient beach access, pet-friendly suites, a soothing spa, upscale dining, and enjoyable activities for families.

New England Road Trip Itinerary: Day 6

I included an extra day in the itinerary because we both felt that spending more time in the Portland and Cape Elizabeth area would be truly worthwhile. Our initial visit felt incredibly rushed, and we found ourselves wishing for more time to fully enjoy these locations.

Portland

Things to do in Portland:

  • Walk the Portland Freedom Trail
  • Explore Cape Elizabeth
  • Go on a lobstering tour
  • Take a cruise around Casco Bay
  • Go on a whale cruise
  • Watch the sunset from a historic sailboat with the Schooner Company
  • Learn about Portland’s history from a Trolley Tour

Read our Guide to Portland to learn more about these activities.

Maine Travel Guide

New England Road Trip Itinerary: Day 7

Boothbay Harbor (Optional)

Time on the Road: 1.5 hours to Boothbay Harbor, then 1 hour to Camden.

We couldn’t pass up the opportunity to try and spot some whales in Maine. When I came across Cap’n Fish’s Cruises and their highly rated Whale and Puffin Cruise in Boothbay Harbor, I could not say no.

Given Boothbay Harbor’s convenient location between Portland and Camden, we decided to include it in our road trip, and it turned out to be a delightful experience. It provided a pleasant break from our long days of driving and sightseeing.

Boothbay Harbor

The first half of the cruise takes you into prime whale territory, providing an amazing experience. On what seemed like an average day, we spotted a few humpback whales beneath the surface.

The guides were exceptionally knowledgeable and engaging narrators, enhancing the overall experience. The second half of the cruise takes you to an island inhabited by puffins, adding an interesting dimension to the tour. Though the puffins were small and somewhat distant, it was still a cool addition to the tour.

Cap’n Fish’s Cruises provides a variety of tours tailored to showcase different types of wildlife over varying durations. I highly recommend considering one of their tours as an addition to your trip!

Drive to Camden. Spend the night in Camden, a coastal town with a delightful Main Street and easy access to outdoor adventures.

Camden

Note: If you want to spend time in Acadia National Park, I recommend staying in Bar Harbor instead of Camden. Read about how you can add on a visit to Acadia in this itinerary.

Where to Stay in Camden

Lord Camden Inn. Reside in a quintessential inn that is located on the main road in downtown Camden. The beautifully decorated rooms are spacious, and are equipped with minifridges and a balcony that overlooks the town. We loved our stay here, the staff was incredibly friendly, and parking was provided.

Camden

Where to Eat in Camden

Peter Ott’s on the Water. Looking for something more casual with a reasonable price? Peter Ott’s on the Water is a great seafood restaurant with scenic views of historic Schooner boats and the marina. This restaurant had a comfortable, friendly vibe with amazing service, and a wide variety of delicious foods.

Peter Ott's on the Water

Peter Ott’s on the Water

Long Grain. This more upscale restaurant has been featured in numerous publications for its variety of amazing Asian cuisine.

40 Paper. This Italian bistro and bar is located in the Knox Woolen Mill, a mill that was in operation from the mid 1800’s to the late 1900’s. With a menu that is frequently changing there is always something new to try throughout the year.

New England Road Trip Itinerary: Day 8

Isle au Haut

Time on the Road: 4 hours round trip

Isle au Haut is a secluded island in Maine’s Penobscot Bay, offering coastal hiking trails, scenic bike routes, and a peaceful fishing village. A significant part of the island is home to Acadia National Park, and its isolation from Bar Harbor keeps the crowds at bay, making Isle au Haut a dream escape for outdoor enthusiasts.

We loved our time on Isle au Haut, often feeling like the island was entirely ours. This was our favorite experience on our trip to Maine, though I only recommend it to experienced hikers, campers, and explorers, as this island is isolated. Hiking about the southern end of the island is the best way to spend a day here.

In our Isle au Haut Guide, learn more about how to take a day trip here.

Robinson Point Lighthouse Isle au Haut

Alternative Suggestion: If you are not up for a remote hiking experience, but still wish to take a day trip to a remote destination, visit Monhegan Island instead! This island is a haven for artists and historians. Some of the island’s main attractions are the artists’ colony, the Monhegan Museum of Art and History, the Monhegan Lighthouse, and peaceful walking trails. Ferries leave from three different spots on the mainland: the Monhegan Boat Line from Port Clyde, Hardy Boat Cruises from New Harbor, and The Balmy Days II from Boothbay Harbor, with each boat having multiple departure times to and from the island.

7 A.M. Drive to Stonington

Start the day early with a 2-hour drive from Camden to Stonington. This is the town where Isle au Haut Boat Services offers trips to and from Isle au Haut.

Year round this ferry takes visitors to Isle au Haut town, a small settlement on the north of the island. From mid-June to September, the ferry will also take visitors to Duck Harbor on the southern end of the island. For the best day trip experience, we recommend riding the ferry all of the way to Duck Harbor and spending the day hiking this side of the island.

Visit the official Isle au Haut Boat Services website for complete schedule listings and rates.

Stonington Maine Harbor

At the moment, reservations for the ferry cannot be made in advance. The ferry runs on a first come, first serve policy. Tickets are limited so it is important to reach Stonington at least an hour before the ferry departure so that you have enough time to reserve a spot. Round-trip and over-night tickets can be purchased on site. Parking is also available on site for all customers.

Make sure to pack food, water, sunscreen, and bug protection. There is no food available on the island outside of Isle au Haut town.

10 A.M. Ferry to Isle au Haut

Board the Isle au Haut ferry. The ferry ride between Stonington and Isle au Haut Town is 45 minutes long. The ferry will drop off passengers at Isle au Haut town dock, and then it will continue another 30 minutes to Duck Harbor, where the remaining passengers will land. There is only one ferry that runs between the three stops, and all passengers with a ticket are guaranteed a seat.

11:30 A.M. Explore Isle au Haut

Land in Duck Harbor and enjoy a beautiful day exploring the island!

Duck Harbor Isle au Haut

A loop hike up the Duck Harbor Mountain Trail, and then along the Goat Trail, Cliff Trail, and Western Head Trail makes for a wonderful day of exploration that encapsulates all of the island’s best views. This loop hike is a total of 4.5 miles. Read our Isle au Haut Guide to get more details about this loop hike.

The hiking trails here are not strenuous, but hikers need to stay vigilant and be able to hike across rocky terrain, over boulders, and along forested trails in a place where there are few people to turn to for assistance. If you have little hiking experience, I do not recommend hiking in Isle au Haut.

Hiking in Isle au Haut

4:00 P.M. Return Ferry to Stonington

Board the ferry at Duck Harbor to ride back to the mainland. Reference the Boat Services schedule to plan the exact time you’ll be leaving Duck Harbor. This time is only for Monday through Saturday June-September and may be subject to change.

5:30 P.M. Stonington to Camden

Have dinner in Stonington and then drive 2 hours back to Camden where you will sleep tonight.

Stonington doesn’t offer an abundance of dining options, but hunger after a day of hiking led us to explore. The standout choice in Stonington is Fin and Fern, conveniently located next to the Boat Services dock. However, it’s a more upscale dining option and it fills up quickly. Instead, we opted for a quick and budget-friendly meal at Stonecutters Kitchen. While the food wasn’t exceptional, it served the purpose for a cheap and easy meal.

New England Road Trip Itinerary: Day 9

Spend a day in Camden to enjoy this idyllic fisherman’s town. Take your pick of how you want to spend this day.

Camden Hills State Park. If you enjoy hiking, visit Camden Hills State Park, an excellent location for outdoor activities. Parking costs $6 for out-of-state adults. Within the park, two of the most renowned hiking trails are Mount Battie and Mount Megunticook. These relatively short trails offer captivating panoramic vistas that overlook the Camden area.

Camden Hills State Park

View from Mt. Megunticook

Sunset Sail. For those who want to experience sailing on a decade’s old schooner, Schooner Appledore hosts a relaxing and interactive sunset sail. The crew does an amazing job entertaining the passengers, allowing them to help hoist the sails, constantly keeping the drinks flowing, and walking around chatting with everyone on board. Each sunset sail hosts around 25 people so prepare for a bit of a crowd. Schooner offers both day sails and sunset sails, each lasting 2 hours. Find more information about timing and prices here.

Camden

Read our Guide to Camden to learn more about how to spend a day in Camden (coming soon).

New England Road Trip Itinerary: Day 10

Time on the Road: 3-hour drive to reach the Kancamagus Highway from Camden.

The Kancamagus Highway is one of New Hampshire’s most scenic drives, as it travels past rolling mountains, lush pine forests, and cascading waterfalls. Along the way are opportunities to complete several short hikes, in addition to quick overlooks to gaze over gorgeous mountain views.

This drive is the perfect way to experience the beauty of the White Mountains in a low effort way. Driving the highway is easy-going, for it follows a wide paved road. It is best driven in the fall when the leaves transform into their autumn glory.

8:00 A.M. Drive to the Kancamagus Highway

Drive 3 hours from Camden, Maine to Conway, New Hampshire. Conway is located on one end of the Kancamagus Highway.

11:00 A.M. Early Lunch

At the start of the Kancamagus Highway lies Cheese Louise , an artisan grilled cheese shack. Cheese Louise offers yummy grab & go meals that will fuel a day of exploration on the Highway. They serve multiple varieties of grilled cheese sandwiches, as well as some salad options. Everything we ate here was fresh and delicious!

11:30 A.M. Drive the Kancamagus Highway

Begin the drive of the Kancamagus Highway. There are many stops to take along the way including waterfall overlooks and short hiking trails. We were interested in just seeing the best sights, which we have listed below in order from Conway to Lincoln.

Albany Covered Bridge. This scenic covered bridge was built in 1858. New England has many covered bridges with the purpose of protecting trusses and decks from harsh weather. This a quick stop and is worthwhile to see one of these scenic bridges. Regular sized vehicles can drive through the bridge, and visitors can walk inside of it.

Albany Covered Bridge

Lower Falls. Lower Falls provides a scenic view of small waterfalls cascading over granite rocks. During the summer, it becomes a popular swimming spot, filled with children playing in the falls. If you’re seeking a quiet and tranquil experience, it might be best to skip this stop unless you’re interested in swimming.

Rocky Gorge. Rocky Gorge is a picturesque stop along the Kancamagus Highway. The Swift River flows through a narrow flume, creating a charming small waterfall. Visitors can walk onto the rocks when the water level is low, and there’s a bridge for great views. Additionally, visitors can cross the bridge and follow a short path to reach Falls Pond.

Rocky Gorge, Kancamagus Highway

Rocky Gorge

Champney Falls. Champney Falls, considered by some as a top experience and by others as a walk in the woods, unfortunately didn’t fit into our schedule. The falls are reached by a 3-mile round-trip hike, attracting those seeking a more immersive nature experience.

Sabbaday Falls. Sabbaday Falls is the most popular stop along the Kancamagus Highway, and for good reason! To reach the Falls there is a short 0.7 round trip hike along a wide gravel path. Boardwalks travel next to the rushing waterfall, granting visitors a close look into the gorge and crystal-clear pools.

Sabbaday Falls, Kancamagus Highway

Sabbaday Falls

The following overlooks each provide scenic views over forested mountains:

  • Sugar Hill Overlook
  • CL Graham Wangan Overlook

Pemigewasset Overlook

  • Hancock Overlook

Pemigewasset Overlook

5:00 Arrive in Lincoln

Arrive in Lincoln, NH. This town is a convenient place to stay during a trip to the White Mountains, since this small town is located only 10 minutes from Franconia Notch State Park, and it sits on one end of the Kancamagus Highway.

Where to Stay in Lincoln

Lincoln is a convenient place to stay during a trip to the White Mountains, since this small town is located only 10 minutes from Franconia Notch State Park, and it sits on one end of the Kancamagus Highway. Sadly, there is not much to see or do in Lincoln, and it is not the prettiest area to wander. It is best to spend your time inside of the park during a stay here.

We stayed at the Hampton Inn and it provided a standard and comfortable hotel experience. Its proximity to many of Lincoln’s restaurants was convenient for our stay.

Other highly rated hotels include the Lincoln Log Cabins (stay in your own private cabin with a view of the mountains), InnSeason Resorts Pollard Brook (a resort with one- and two-bedroom suites, making this a great pick for families), and Launchpoint Lodge (a beautiful property that is adult-only).

New England Road Trip Itinerary: Day 11

Franconia Notch State Park lies in the heart of the White Mountains National Forest. With forested ridges to climb, gorges to wander, lakes to play in, and signs for moose crossing, this is a park perfect for outdoor lovers, family road trippers, and weekend campers.

You have the whole day to see this park. Read our Guide to Franconia Notch State Park for a full list of things to do here.

We spent the day hiking the Franconia Ridge Loop , a challenging 8-mile hike that takes travelers to the summit of three mountains. With steep grades and considerable distance, it’s ideal for fit mountaineers seeking stunning views of New Hampshire’s forests and distant peaks. But despite its difficulty, completing this loop doesn’t require extensive hiking experience. This hike takes 6-8 hours to complete. Read more about our experience hiking the Franconia Ridge Loop here.

Franconia Ridge Loop

Of all of the activities we did in Franconia Notch State Park, hiking the Franconia Ridge Loop was our favorite as it provided the most beautiful views and rewarding experience. However, there are many other great things to do here that do not require extensive hiking. These experiences include:

Flume Gorge. Franconia Notch’s Flume Gorge is a beautiful outdoor adventure past cascading waterfalls, across historic covered bridges, and amidst New Hampshire’s pristine forest. Hiking the Flume Gorge is a top experience in Franconia Notch State Park, and its two-mile-long trail is possible for people of all ages to enjoy.

Flume Gorge Franconia Notch

Cannon Mountain Aerial Tramway and Ski Area. The Cannon Mountain Aerial Tramway is the nation’s first passenger aerial tramway and has been taking visitors to see its grand views for over 80 years. On a clear day, you can see the mountains of four states and Canada. We greatly enjoyed our experience at Cannon Mountain, and found it a great thing to do, especially for non-hikers.

Cannon Mountain

Echo Lake . Echo Lake is a scenic natural lake nestled amongst the White Mountains. Canoes, kayaks, and peddle boats are available for rent at the Lake, allowing visitors to take in its crystalline surface and wondrous views.

Artists Bluff Trail. A popular hike from Echo Lake is the Artists Bluff Trail. This is a 1.5-mile loop hike that takes hikers to a viewpoint over Echo Lake and Cannon Mountain. This hike is relatively easy and is many visitors’ favorite experience in the Park.

Echo Lake Artists Bluff Trail

View of Echo Lake in the fall from the Artists Bluff Trail | haveseen/shutterstock.com

New England Road Trip Itinerary: Day 12

Drive or Fly Home

Return home or continue your travels.

If you have some time in the morning, consider adding a short activity in Franconia Notch State Park. We chose to explore the Flume Gorge before heading home and found it to be a serene and enjoyable short walk. The walk around the Flume Gorge typically takes about an hour.

Best Time to Do This New England Road Trip

The best time to do this road trip is in September to early October when the summer heat fades from Cape Cod and New Hampshire’s forests start to become an assortment of reds, yellows, and oranges.

Note that ferry access to Isle au Haut’s Duck Harbor is only available until early October.

Franconia Notch State Park is subject to seasonal closures from late October to early May.

We did this road trip in early August and still loved the experience. We were able to enjoy warm summer days, lush green forests, and fully accessible trails, but the wow factor of the Northeast’s autumn foliage was missing.

If you have any questions about this New England road trip itinerary let us know in the comment section below.

More Information for Your Trip to New England

BOSTON: For information about Boston, read our article Best Things to Do in Boston . We also have a detailed guide on how to day trip to Plymouth, Lexington, and Concord from Boston.

NEW HAMPSHIRE: Don’t miss our article about the best things to do in Franconia Notch State Park and how to hike the Franconia Ridge Loop . We also have a guide to 10 great stops along the Kancamagus Highway .

MAINE: Don’t miss our article about the best things to do in Cape Elizabeth  and our guide to Portland.

ACADIA NATIONAL PARK: Check out our Acadia National Park Travel Guide for important travel information, sample itineraries, and how to plan your visit. For a list of must-have experiences, read our article Best Things to Do in Acadia National Park. Go off the beaten path and explore Isle au Haut.

USA ROAD TRIPS: Planning your next big adventure in the USA? Check our our USA Road Trip Guide for travel ideas and sample itineraries.

If this is part of a bigger road trip through the USA, visit our United States Travel Guide  for more inspiration and travel planning tips.

New England Road Trip

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Portland

Hi Trekkers,

In Kara’s New England road trip, day 11 mentions the Franconia Ridge Loop trail as a “hard 12-mile hike”. But the detailed section lists it as 8.27. If I follow your route as detailed, will I steer clear of the 12 mile version? I used to just assume when the kids were kids, if they can do it, I can. But now they are adult hiking beasts, so I want to make sure I know what I’m signing up for! Love the website and all of the content/guidance that it provides. I’ve been referencing it for years. Thank you.

Avatar for Julie

Hello Roy. Thank you for writing in and for pointing that out. I talked with Kara and the correct distance is 8.27 miles according to her GPS data and other sources also list the distance at roughly 8 miles. I have corrected it in this itinerary. It’s a challenging hike but 8 miles makes it much more doable! Cheers, Julie

Avatar for Michael Lowe

Looking for good retirement road trips in the USA

This is a good one. We have more to choose from on our article 18 Road Trips in the USA . Cheers, Julie

Avatar for Paul Lorden

I’m from the UK and planning a roadtrip around New England for later this year. We’re mostly hoping to visit the White Mountain National Forest (particularly Mt Washington, Crawford Notch, Kancamagus Highway, Franconia Notch) and then head over to Stowe before heading south through the Green Mountain National Forest.

Do you know if I would need any park passes or USFS passes or day passes to visit these areas please.

Hello Paul. You will need to pay a day use fee when you enter Franconia Notch State Park and a parking fee for stops along the Kancamagus Highway. But you don’t have any National Parks listed so you won’t need a park pass. Cheers, Julie

Avatar for Susan H

I am a huge fan of your Earth Trekkers website and refer to it often. I have utilized the state maps of your trips (example, Grand Teton, Yellowstone and Glacier) which gave a visual of the full route. I do not see a map for the 12 days in the Northeast.

That’s a good pickup. We will put it on our to do list and try to get it on here as quickly as possible. Cheers, Julie

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Things to do

The ultimate 10-day new england road trip itinerary.

New England, with its quaint villages, idyllic landscapes, rich history, and mouthwatering culinary experiences, is a treasure chest of delights waiting to be unlocked. From the rugged beauty of the Maine coastline to the vibrant, artistic vibe of Providence, this is a region that never fails to enchant.

If you’re up for the crisp smell of the ocean mingled with pine trees, the rustic charm of cobblestone streets lined with centuries-old houses, and the taste of the most succulent seafood freshly plucked from the sea, then you have to start planning your New England road trip!

» You might be interested in a shorter version with this Boston to Bar Harbor road trip itinerary.

Mt. Battie, Maine

» Looking for more travel inspiration in the United States ? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit . Here are a few more fabulous U.S. Cities to visit .

The only real problem is deciding what to do and see and how to fit everything into ten days. Lucky for you, we’ve done this road trip multiple times and have passed through these states on a number of different trips, so we have the knowledge to help you plan an amazing time on one of the best road trips in the United States .

Table of Contents

Essential New England Road Trip Info

Comprising six states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont -there’s a lot of ground to cover during a New England driving tour. It’s not a small amount of driving, despite how close together many of these states are. So if you’re planning to embark on this road trip, keep this in mind.

You can either fly into a set starting point – we recommend Boston – or you can drive in from where ever you’re located in the United States. In any case, you’re going to need a car – either your own or a rental car . If you’re renting, we suggest going through Discover Cars to get the best deals from all the top car rental companies in one place.

How to Get to New England

If traveling from Europe or another destination outside the States, you’ll fly into Boston for this itinerary. Considering the region’s most popular international airport, Boston Logan International Airport (BOS) is where your trip will start and end.

If Boston doesn’t work for you, you can also fly into New York City , Philadelphia, or even Washington, DC. It will just take you a little longer to drive to the start point of this road trip, but there is plenty to see along the way.

Connecticut in Fall

When Should You Do on a New England Trip?

Unless you’re a winter die-hard, the best time to visit New England is undoubtedly during the fall, from September to December, or spring, from March to June. 

Fall is when the landscape takes on a magical element with changing colors in every shade of gold, orange, red, and brown imaginable. Aside from that, the crisp, clear fall air and the New England sun bursting through the morning mists are second to none, making it one of the best fall destinations in the USA .

If you can’t swing a fall road trip, the second best time is during spring. This is before the heat of the summer really sets in, so temperatures will be mild and enjoyable. I would definitely not go in summer, if at all possible, because it can get really hot and humid.

New England Road Trip Itinerary

Are you ready to buckle up and join me on a 10-day road trip across these six picturesque states? I’m thrilled to share this thoroughly curated itinerary that will ensure you make the most out of this journey, exploring the hidden gems as well as the must-see spots.

Whether you’re a history buff, a foodie, a nature enthusiast, or simply someone who enjoys the thrill of exploring new places, this 10-day New England road trip has something for everyone. So pack your bags, put on your favorite road trip playlist, and let’s hit the road.

Boston, Massachusetts (Day 1)

boston harbor

After arriving in Boston, Massachusetts , you can jump directly into the first day of your trip by visiting Boston. Drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, you’ll find a million historical things to see alongside plenty of sports bars to grab a beer in at the end of your day. While there’s no way to see the best of Boston in one day, we suggest you include these highlights on your first day:

  • Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
  • Explore the Boston Tea Party Ships and Museums
  • Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
  • Grab a few snapshots of America’s most photographed street, Acorn Street
  • Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem, Massachusetts & Portland, Maine (Day 2)

salem

Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you’ll drive for about 40 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. If you’re visiting during October, prepare for an overload of everything spooky. No matter when you’re in town, here are some spots you shouldn’t skip:

  • The Salem Witch Museum
  • Salem Witch Trials Memorial
  • The House of the Seven Gables

When you’re done exploring spooky Salem, jump back on Route 127. After about an hour and forty minutes, you’ll reach Portland, Maine. 

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews and distilleries. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

  • Visit Fort Williams Park and the Portland Head Light
  • Tackle a brewery tour of Portland to some local craft breweries
  • Shop the local boutiques and specialty shops of Old Port
  • Grab a sunset view along the Eastern Promenade
  • Eat lobster rolls at Luke’s Lobster on the pier

Tours to look out for while you’re in Portland:

  • Old Port Culinary Walking Tour
  • Cusco Bay Sea Kayaking Tour
  • A Walk Through Time Tour in Portland 

Where to stay: Portland Regency Hotel & Spa

Bar Harbor & Acadia National Park, Maine (Day 3)

Bar Harbor, Maine

Your third day along this New England trip requires an early start and a three-hour drive, but the rewards are totally worth it. Driving from Portland to Bar Harbor, the beach town gateway to Acadia National Park, prepare for some out-of-this-world scenery.

Along the route, you’ll pass through a few towns worth a stop. The first is Bristol, where you can spend a minute or two at the Pemaquid Point Lighthouse , then stop at the Camden Hills State Park in Camden to see the view from the top of Mt. Battie.

After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park. You need a U.S. Park Pass to get in. If you’re going to be visiting more than one park in the year, you should definitely consider getting the America the Beautiful annual pass, which is just $79.99 from REI.

On Maine’s largest island, Mount Desert Island, the 47,000-acre Acadia National Park has dramatic mountains, picturesque lakes, and endless miles of hiking trails. It’s one of the biggest draws to this part of the U.S.

The top three things to add to your Acadia itinerary include:

  • Hiking to the summit of Cadillac Mountain (vehicle reservations are required for Cadillac Summit Road from May 25 through Oct 22). Book online.
  • Kayaking on Swan Lake
  • Biking or driving the Park Loop Road. The Park Loop Road can be very crowded. Have a backup plan if the area you wish to visit is full.

Where to stay: Bar Harbor Inn

White Mountain National Forest, New Hampshire (Day 4)

White Mountain National Forest

While you technically did venture into stunning New Hampshire earlier in your road trip, day four is all about heading to and roaming around one of the state’s top attractions. The drive to get there is another 3 hours 30 min drive, so get up early!

Topping most driving tours of New England, especially those focused on New Hampshire, White Mountain National Forest is a beautiful collection of natural landscapes. The best thing about the National Forest is that there are many unique activities to indulge in regardless of what time of year you’re visiting.

  • In springtime, thanks to warmer weather and melting snow, the forest delivers the perfect setting for hiking and camping.
  • During the summer, you can fill your day by hiking, fishing, or canoeing.
  • When fall arrives, you should set out to drive New Hampshire’s scenic Kancamagus Highway.
  • Wintertime brings with it a lot of snow-capped mountains fit for winter sports enthusiasts at numerous ski resorts.

Where to stay: The Inn at Thornhill & Spa

Stowe, Vermont (Day 5)

Stowe

Once you’ve said farewell to New Hampshire, it’s time to head to NEK or the North-East Kingdom of Vermont. It’s a 1 hour 30 minute drive. Known for its spectacular green mountains, eye-catching lakes, and charming small farms, the state is a buzzworthy must-visit.

On the way to Stowe, you’ll stop in Waterbury for a genuine pilgrimage to the ice cream empire and the original store of Ben & Jerry’s.

Next up is a short 20-minute drive north to the ski resort town of Stowe. This world-famous ski destination showcases an authentic small-town charm, a lively main street, and some iconic steepled churches.

Be sure to check out some of Stowe’s one-of-a-kind local favorites, such as Laughing Moon Chocolates, Shaw’s General Store, and The Deep End (the hippest pizza place in the state). Other options here include:

  • Skiing at the Trapp Family Lodge
  • Hiking in Green Mountain National Forest
  • Heading on a scenic drive on Mountain Road

Where to stay: The Lodge at Spruce Peak

Litchfield & Mystic, Connecticut (Day 6)

Mystic Seaport Connecticut

Another early start on day six, you’ll drive down the Route 100 Scenic Byway, Vermont’s longest highway, through Wilmington, across the border into Connecticut. First stop of the day? Litchfield; a charming New England town brimming with local history. It’s a 4-hour drive to get there.

Founded in 1719, today, the town is a popular tourist destination known for its antique shops, numerous art galleries, and historic homes.

Delving further into Connecticut, you’ll head east to the town of Mystic. This historic seaport sits snuggly on the Mystic River and is most famous for its maritime heritage and the setting of the 1988 film Mystic Pizza .

Here are some highlights in Mystic:

  • Visit the Mystic Seaport Museum , one of the largest in the world
  • Explore early colonial farm life at the Denison Homestead
  • Dive into some aquatic adventures at the Mystic Aquarium
  • Hike a trail or two in Bluff Point State Park

Where to stay: Hilton Mystic

Newport, Rhode Island (Day 7)

newport coast

Continuing the coastal New England road trip, the next stop along your journey is in Rhode Island. Although it’s the smallest state in the US, it is home to some of the country’s most historic towns, most notably Newport. This is only an hour drive.

This seaside town, once a summer retreat for America’s most wealthy families, boasts breathtakingly stunning mansions built during the Gilded Age and is quite the sight to behold. Beyond that, you’ll find pristine beaches and some of the best seafood in the country here.

When you’re planning your day in Newport, be sure to include these must-do activities:

  • Stroll along Cliff Walk, a coastal 3.5-mile pathway hugging the Atlantic Ocean
  • Indulge in some retail therapy along Bellevue Avenue and Thames Street
  • Head out wine tasting at Greenvale Vineyards
  • Tour the famous Newport Mansions
  • Explore Bowen’s Wharf or take a boat cruise from Long Wharf
  • Relax on the sands of Easton Beach

Where to stay: Newport Marriott

Cape Cod (Day 8)

cape cod

Next up, and after an entire week on the road, it’s time for some rest and relaxation on the flexed arm of Massachusetts, in Cape Cod, a 1-hour 30-minute drive. Sitting on a peninsula in the state’s southeastern region, Cape Cod has long been a summer destination for the rich and famous.

Now if you’ve ever wondered why New England beach vacations are so popular, the almost 560 miles of coastline that encircle Cape Cod provide a clear answer. Yes, there are many great towns here worthy of a stay, but for this road trip, you’ll spend the day and night in Sandwich.

The official oldest English settlement in Cape Cod, Sandwich, dates back to 1639 and stuns with calm beachfront, quaint eateries, and a vibrant historic district. Fill your day in Sandwich with some of these standouts:

  • Breakfast at Cafe Riverview
  • Stroll along East Sandwich Beach
  • Visit Sandwich Boardwalk
  • Explore the Sandwich Historic District
  • Indulge in the best lobster in town at Mattakeese Wharf

Where to stay: Sandwich Lodge & Resort

Plymouth, Massachusetts (Day 9)

Plymouth Massachusetts

What would an itinerary for a New England road trip be without a stop in Plymouth? That’s why your second-to-last day in the area is all about exploring the town that dates back to 1620. It’s a 30-minute drive from Cape Cod.

Today this quintessential New England town is most known as the site where the very first Thanksgiving took place and is home to Plymouth Rock. Steeped in history, this is where the Pilgrims first landed way back when.

With all that history, here are a few top spots you should visit while in Plymouth:

  • Explore Plimoth Patuxent , a living history museum with a replica of the Mayflower ship
  • Grab a few snapshots at Plymouth Rock and delve into the Pilgrim Hall Museum
  • Roam around Plymouth’s historic downtown harbor area, home to several notable buildings such as the Plymouth Courthouse
  • Cap off your day with a stroll along Plymouth’s famously historic waterfront and catch the sunset over Cape Cod

Where to stay: Thomas Sea Suites at Harbourtown

Boston, Massachusetts (Day 10)

Boston harbor

Finally ending your epic 10-day New England road trip, you’re back in Boston . Luckily the drive from Plymouth to Boston is only 45 minutes to an hour, so you can start the day a bit later and still be back in Beantown with some time to spare for any extra activities.

We’d recommend fitting anything you didn’t have time for on day one into your final day. If you’ve got a few extra hours, here are some other Boston highlights to add:

  • For history lovers, pay a visit to the USS Constitution Museum or the Paul Revere House
  • Art lovers should definitely head to the Isabella Stewart Gardner Museum and the Museum of Fine Arts
  • Sports fanatics should take a one-hour tour of Fenway Park or catch a Boston Red Sox game ( check their calendar here )
  • For food lovers, be sure to check out our foodie guide to Boston .

Where to stay: Hyatt Centric Faneuil Hall Boston

Wrapping Up Your Road Trip Through New England

There you have it – the best road trip through New England you could possibly do in ten days. Although numerous other attractions and standout activities can be included on any trip, this New England trip itinerary features the best of the best.

Of course, you can play around with other vacation ideas in New England or discover hidden travel tips heading off-the-beaten-path. Now all you have to do is decide when to go and prepare for some exciting road-tripping in New England.

Be Prepared For Travel

Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

  • Find and book the best hotel (our favorite booking site is Expedia)
  • Research flight options (our favorite tool is Skyscanner )
  • Book a tour (we always use Viator to find the best tours)
  • Rent a car through Discover Cars (they search the best deals for you!)

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Laura

Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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Adventures in New England

Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

things to do on Martha's Vineyard

47 Fabulous Day Trips in New England

winter road trips in new england

Whatever season you are visiting, New England has many spots perfect for day trips. We have green forested mountains, rocky coastlines, colonial history, and extraordinary seafood. If you plan a New England road trip, this New England day trip guide can help you plan where you should visit. I am blessed that many of these spots are close to my home base of Rhode Island. Boston is an even more ideal base. Please enjoy this local’s guide to the best day trips in New England.

Newport RI bike rides

  • Spend the day walking through the paths of Sachuest Point National Wildlife Refuge in Middletown, Rhode Island, with abundant wildlife and overlooks to the ocean. After exploring, head down to Flo’s Clam Shack for a true New England lunch.
  • Visit another of Rhode Island’s prettiest spots, Napa Tree Point in Westerly. Across the bay, you can also visit the Watch Hill Lighthouse. Although you can’t go into the lighthouse, a small museum is open in the summer. Enjoy lunch or the sunset from the ritzy Ocean House Hotel deck.
  • Take a quick ferry ride over to Block Island , Rhode Island, where you can enjoy the beaches, see its two lighthouses and the famous Mohegan Bluffs, and listen to live bands at Ballards Beach Club.
  •  If you want to explore a more upscale island, visit Nantucket Island in Massachusetts.
  • Take a ferry from Boston or drive down Cape Cod to reach the outer Cape and Provincetown, Massachusetts, a colorful town with gorgeous sand dunes. Read my Outer Cape Guide.
  • Take a bike ride on Cape Cod. Check out my list of the best bike trails on the Cape.
  • Martha’s Vineyard , Massachusetts, is my favorite of the New England islands. It is full of cute towns, historic gingerbread houses, ponds, beaches, and Kennedy history. You can catch a ferry from multiple spots in Massachusetts and Rhode Island.
  • Head up to the White Mountains in New Hampshire for a fall drive, waterfall hikes, ski resorts, or to take the kids to an amusement park.
  • Explore the Cliff Walk and enormous early 1900s mansions in Newport, Rhode Island. Another day trip idea near Newport is to catch a polo game at the Newport International Polo Fields, then have dinner at Newport Vineyards.
  • Spend the day visiting a vineyard which often have beautiful restaurants. Southern Connecticut has a wine trail , and Maine has interesting fruit wines. Wineries can be found throughout the region.
  • Take a ride to Jamestown, Rhode Island. This island in the middle of Narragansett Bay has a historic grinding windmill to tour and excellent cider donuts at Windmist Farm. After those activities, take a ferry over to Rose Island and Newport.
  • For another day trip in Jamestown, have lunch on Main Street and then visit Beavertail State Park. This park has a lighthouse to tour, a lawn perfect for kite flying, hiking trails, and some of Rhode Island’s most panoramic sunset views.
  • If you are looking for something to do in the fall, be sure to visit a pick-your-own apple orchard. Most of them also have some other activities, such as stores or rides, and many sell fresh apple cider donuts.
  • Even better, you can see apple cider being made at a cider mill, such as BF Clyde’s in Mystic. The place is like a carnival with live music and food in the fall. Right up the road is a historic cemetery surrounded by stone walls, a very common New England site.
  • Speaking of New England carnivals, the largest one occurs in the fall in Springfield, Massachusetts- the Big E . Aside from the normal carnival activities and food, the Eastern States Exposition has copies of all five New England state houses filled with local food and goods.
  • If you aren’t in Springfield when the Big E is open, there is still plenty to fill a day in the area. Visit the Yankee Candle Factory, the Basketball Hall of Fame, or the Springfield Museums.
  • Maine is famous for its blueberries, but you can also go blueberry picking in any New England state.
  • It is easy to fill a day in Mystic, Connecticut. It has the Mystic Aquarium, a historic seaport museum, a cute Main Street, and a working drawbridge.
  • Essex, Connecticut , sits on the banks of the Connecticut River. It is worth taking the ferry across the river, having lunch among the colonial houses on Main Street, and seeing Gillette Castle and the opera house. Nearby is The Florence Griswold Museum, the spot of the beginning of American Impressionism.
  • Visit New Haven, Connecticut, to try some of New England’s most famous pizza and see the campus of Yale University.
  • Wethersfield, Connecticut, is the oldest town in the state. It has a pleasant, walkable old town and many historical museums.
  • Visit a sugar shack. Vermont is known for its maple syrup, but any New England state has sugar shacks open in winter to see the syrup-making process.
  • Hunt waterfalls along the Kancamagus Highway, New Hampshire. This highway has some of the best foliage in the fall.
  • Woodstock, Vermont , has been named the quintessential New England town with its darling downtown, historic inn, and multiple covered bridges.
  • Hike Mount Washington, New Hampshire, the highest peak in New England. If you are not up to the challenge, you can drive up or take the train. There are also many other worthwhile shorter mountains to climb, such as Mount Major, Mount Monadnock, and Mount Tumbledown .
  • Visit a lavender or sunflower farm. Summer provides ample opportunities to tour flower fields. Check out my New England flower field guide.
  • During summer, lupines bloom in New Hampshire and Maine. Plan a drive to see them.
  • The highlight of Shelburne, Massachusetts, is the Bridge of Flowers, but there are also many other things to do, such as hiking.
  • The Mohawk Trail is a mountainous road through the Berkshires of Massachusetts. While there, stop to hike or explore small towns and farms.
  • Salem, Massachusetts, is the home of the Salem Witch Trails and the stomping grounds of Nathaniel Hawthorne.
  • Boston, Massachusetts, was at the center of the new United States of America. 16 significant historical sites can be visited by following the Freedom Trail.
  • Plymouth, Massachusett, is the site of the first permanent Pilgrim settlement in the United States. You can visit the historical village museum, or even celebrate a Thanksgiving dinner there now.
  • Old Sturbridge Village is a recreation of an 1830 colonial village in Massachusetts.
  • Rockport, Massachusetts, is famous for its beaches and inspiring seaside views.
  • Visit an aquarium- Either the Mystic Aquarium or the New England Aquarium in Boston.
  • New Bedford, Massachusetts , is an old whale town with a strong Portuguese presence. It has a whaling museum and the church that inspired Moby Dick.
  • Visit a cranberry bog. You can even tour one and wade in it. Read about my experience.
  • Go back in time to Concord, Massachusetts, with the transcendentalists at Walden Pond, or check out American Revolution battle sites.
  • Take a whale watch. They are available all around the coastline.
  • Get out onto the water in New Hampshire’s Lake District. One of my favorite stops is Meredith on Lake Winnipesaukee.
  • Take a road trip through the Green Mountains of Vermont, stopping at waterfalls, art galleries, and at the Ben and Jerry Factory.
  • Burlington, Vermont, sits on the banks of Lake Champlain and has a vibrant art and history scene.
  • Take a canoe trip or a float down a river.
  • Portland, Maine, lies on the coast of southern Maine. It has excellent food, hiking, and shopping. Read my article about 47 fabulous things to do in Portland.
  • Take the half-hour ferry ride from Portland to Peaks Island, Maine, where you can spend the day bike riding around the island.
  • Drive up the Maine coast, which is filled with lovely waterfront towns like Ogunquit and Old Orchard Beach.
  • The northeast’s oldest national park is Acadia National Park . Ideally, you would have more time to explore this wooded park along the cliffs of Maine’s coast, but at least get yourself here for a day.

best new england day trips

Are you planning a trip to New England? Do you have any New England road trips that you love that I missed? Please let me know in the comments.

Whether you are looking for day trips in New England or help to plan a New England road trip, read on for ideas. #BestNewEnglanddaytrips #NewEnglandUSA #NewEnglandTravel

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8 thoughts on “47 Fabulous Day Trips in New England”

Gosh so many things to do. I spent a working week in Boston/Harvard many years ago, but we didn’t have much time to venture out, the only trip we did was to Saleem. I think that I need a return trip to visit Martha’s vineyard, do some whale watching, and walk on some of those trails.

I can see I need to plan a very long visit to New England. Or plan many trips to enjoy this great list of day trips in New England. I love the variety in the activities you have highlighted. And that there are things for all seasons. We definitely need to pick a few things and plan a first visit.

I’m headed to New England on a mini-roadtrip in a month, so I loved reading this list. I’m planning to drive the Kancamagus Highway based on your recommendation from another post. What are your favorite stops along it? Thanks!

Definitely take a few waterfall hikes. Search for my New Hampshire hikes post. The views will be stunning from the lookouts!

There are so many great options for day trips in New England, and it’s awesome that you don’t have to drive for hours and hours just to cross one state border! I would really like to visit Block Island. I think it is exactly what I would love as a traveler – natural beauty, small town vibes, and unique landmarks to visit such as the lighthouses.

Hillstead in Farmington Connecticut is a really special place. A beautiful old home filled with the most wonderful impressionist paintings. The grounds are spectacular as well.

What a great list of day trips! I would love to visit Acadia National Park with my family.

It’s gonna take quite some time to complete this list of incredible destinations. Some of these destinations I have gone to. Now I have been provided with other great destinations to try! Warm Summer Regards!

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10 Routes That Make For The Perfect New England Road Trip

W ith imposing mountain ranges on one side, and a beautiful coastline that overlooks the Atlantic Ocean , the New England region definitely has to be on anyone's bucket list when it comes to wanting a versatile road trip that could be as short as cruising along Connecticut, to as lengthy as following all the way along the region's coastal landmarks .

Whatever the case may be, some of the most famous United States road trip routes can be found in New England, serving as relaxing pathways and being a great way of showcasing both the land's natural beauty and the charming towns along the way .

Olympic Trail Scenic Byway

Starting off strong, and entering from the east side of New York, the Olympic Trail Scenic Byway begins with a first-hand view of the majestic Lake Ontario and ends at the Vermont side of Lake Champlain.

  • The trail gets its name due to going straight through the historic village of Lake Placid , which is known for having hosted the Winter Olympic Games several times in the 20th century.

The whole length will be met by cozy mountainous villages, towns, and peaceful lakes to stop by and turn a trip into an adventure. And, if that wasn't enough, the whole route has the Adirondack Mountains follow along in the distance for the perfect landscape in the background of each picture taken.

  • Length: 170 miles
  • Route: Sackets Harbor → Keeseville

There's a much shorter version of the trail that connects Keeseville with Lake Placid.

Maine's Coastal Tour

Maine's coastline is a long and beautiful stretch of land that perfectly meets with the ocean for amazing views every second of the way.

The whole road can be either taken in small sections or just going from one point to another and turning into a several-day vacation that takes the best from the most picturesque side of Maine .

  • Length: 272 miles
  • Route: Kennebunkport → Bar Harbor

Related: Discover The Charm Of New England: 10 Essential Stops On The New York City To Boston Route

Vermont Route 100

Out of all the states that make the region of New England, Vermont has got to be the most stunning when it comes to natural landscapes comprised of huge forests, beautiful lakes, and picturesque mountains throughout the whole state.

Route 100 makes for a drive that goes from one end of Vermont to the other, going through all sorts of highlights like magical roadside castles and amazing views of the Green Mountains basically from start to finish.

  • Length: 217 miles
  • Route: Moss Glen Falls → Stamford

Related: Exploring The Beauty Of The Florida Keys On A Road Trip Along The Overseas Highway

Kancamagus Scenic Byway

Making for a totally surreal experience to be lived during fall, the Kancamagus Scenic Byway consists of a much shorter drive that can still be considered a perfect New England road trip.

Filled with the aesthetic beauty and rich history of New Hampshire, the route has been designated an American Scenic Byway, with the main highlights of the trip being the luscious forest pathways inside the White Mountain National Forest and first-hand encounters with clear rivers and waterfalls.

  • Length: 34.5 miles
  • Route: Bath → Conway

Mohawk Scenic Byway

As a route that showcases Massachusetts' history, culture, and natural beauty, the Mohawk Scenic Byway joins the Connecticut River Valley with the historical venues of the Berkshire Mountains .

The route goes through what once was a footpath used by Native Americans, well before it was turned into the state’s first designated scenic auto touring road, and along historic villages to make for great attractions that serve as marvelous breaks between driving.

  • Length: 69 miles
  • Route: Connecticut River Valley → Berkshire Mountains

Old King's Highway

Following along historic route 6A, Old King's Highway is famous for being both the oldest road leading to Cape Cod and for having been a massive part of the region's history, serving as a trail for Native Americans to pass by and later becoming a cart path for farmers to transport their produce.

Nowadays, it's used as a scenic driveway along the coastline of Massachusetts for a short road trip or to get to one of the many beautiful beaches .

  • Length: 58 miles
  • Route: Sandwich → Cape Cod

Park Loop Road

Passing right through Acadia National Park on Mount Desert Island , Park Loop Road takes visitors on a 3-hour-long trip through the park's most scenic route and most popular attractions to be found, such as the Heart of Acadia, Cadillac Mountain, and Jordan Pond.

However, due to being such a popular route, there's bound to be a lot of traffic, especially during peak travel seasons such as summer and fall, so be prepared to share the road with plenty of people.

  • Length: 27 miles
  • Route: Paradise Hill Road → Sand Beach

Related: Road Trip Rules: 10 Towns You Need To Visit On Route 93

Skiers Paradise

As a much shorter alternative to experience the snowy side of Vermont, this route goes by what's known as Skiers Paradise , a set of mountains, slopes, and wonderful ski resorts perfect for daredevil tourists .

It's not necessary to go up the mountains to fully appreciate the landscape, though, as being able to ride across this snow wonderland is more than enough to make for an unforgettable road trip.

  • Length: 80 miles
  • Route: Stowe → Woodstock

Bold Coast Scenic Byway

Also turning a much longer route into a more manageable drive, the Bold Coast Scenic Byway goes through 125 miles of Maine's coastline from the southeast region and passes by the bordering area of Acadia National Park for amazing views throughout the whole way.

What makes this one of the best road trips in New England, is that it also celebrates the Bold Coast way of life by going through the most prolific fishing villages for a chance to taste some of the best seafood in the country .

  • Length: 125 miles
  • Route: Milbridge → Eastport

Rural Connecticut

For a more quaint and peaceful drive along farms and meadows, why not travel across the rural side of Connecticut? Sure, it might be much flatter and quieter than every other route on the list, but that's exactly what makes it stand out.

Just pass by farmsteads and peaceful towns as the wind slowly blows on the fields.

  • Length: 40 miles
  • Route: Old Norwich → Woodstock

10 Routes That Make For The Perfect New England Road Trip

Inspired Routes

17 Exciting Winter Road Trips USA: Scenic and Unexpected Routes You’ll Love

Posted on Published: November 17, 2023  - Last updated: November 28, 2023

Who says road tripping has to end when summer is over? Whether you’re hoping to escape the cold or hit the snowy ski slopes, here are the most amazing winter road trips around the US!

winter road trips view of lighthouse along coast with dusting of snow

This post may contain affiliate links. For more info, see my  disclosures .

For some parts of the US, winter transforms landscapes into breathtaking scenes with snow-covered mountains, frozen lakes and dazzling white trees. Yet some regions in the US offer an escape from the snowy weather. Seeking sun is like an escape plan from the winter gloom!

So, which is better for you?

This list of the best road trips in winter takes you on routes like through quaint snowy New England towns or the sunny Florida beaches. Whether you love skiing and winter hikes or desert landscapes and palm trees, this list has something for everyone!

Must-see video: winter road trips

Map of road trips in winter

From marveling at the frozen waterfalls in Oregon to exploring desert landscapes in Arizona, these winter road trips should not be missed.

Check out the map below to start planning your US winter road trip Each icon on the map represents a city or stop along the routes below.

By the way, since I haven’t been everywhere (yet), I’ve enlisted the help of some of my fellow travel writers to prepare these recommendations for the best US road trips in winter. Enjoy!

Packing list for road trips in the winter

best us winter road trips view of white mountain and snow covered trees with view into the distance

It’s no secret that temperatures drop throughout the United States during the winter months. Even Florida sees chillier nights than what you may be expecting. In order to have an enjoyable winter road trip, it’s important to be prepared.

Here’s a packing list to get you started!

  • Snacks/food and water. Perfect for any weather, you’ll want to stay fueled during your road trip adventure. My family especially loves trail mix , beef jerky and fresh fruits and veggies for snacks.
  • Reusable bottles. More eco-friendly than single use plastic, fill up at restaurants, national park refill stations or your hotel/accommodations.
  • Collapsible cooler. Keep your cold items cold when needed, and fold it down to store or pack it away.
  • Satellite communicator. Critical for outside communication in an emergency, this device allows for 2-way communication, even if you don’t have cell phone service. This satellite communicator has traveled with me everywhere for years!
  • First aid kit. Another emergency item. This travel-size kit is small enough to pack in a suitcase if your’e flying to your road trip destination, too.
  • GoPro. Capture really cool road trip footage (when you’re not driving, of course). My GoPro has traveled the country – and the world with me, actually, and I wouldn’t leave home without it.

road trip snacks view of container of fruits and veggies in car

What to pack for road trips to cold climates…

  • Extra layers. In case it’s colder than you expect when adventuring around. Don’t forget the hats and gloves, too!
  • Blanket. For emergencies or just to stay extra cozy!
  • Hand warmers. Another handy item just in case.

Best US winter road trips

Let the winter road trip planning begin! Below you will find the very best winter road trips in the United States. From coast to coast and beyond, this list has some really fun ideas!

1. Denver to Albuquerque

garden of the gods colorado view of red rocks against snowcapped mountains during winter road trips

  • Distance: 449 miles
  • Recommended time: 2 – 7 days

One of the very best winter road trips is the drive from Denver, Colorado, to Albuquerque, New Mexico! With adventures around every turn, this road trip is so amazing in the winter.

Interstate 25 south from Denver in to New Mexico is such a gem. There are so many places to stop and things to see along the way! You could spend a day (or more) in Denver seeing the main sights before heading south.

Be sure to spend some time in Colorado Springs, including Pikes Peak and Garden of the Gods. (My favorite trail in the park is the Siamese Twins Trail .) From there, if you have the time, take the quick detour to see America’s highest suspension bridge – the Royal Gorge Bridge and Park in Canon City.

Next, spend a day exploring Great Sand Dunes National Park – an underrated park in the USA! And during the winter, you’ll likely encounter very few crowds, making it extra peaceful.

As you enter New Mexico, you’ll want to visit Taos, and specifically the Taos Pueblo  indigenous village. Taos Ski Valley is also a popular wintertime activity if you want to hit the slopes!

Next is Santa Fe, which is full of southwestern charm with plenty of museums and indoor activities to do in winter. Be sure to visit Santa Fe Old Town for amazing food, artisans selling crafts and so much more.

Finally, as you make your way to Albuquerque, you could spend a day – or many – enjoying Old Town Albuquerque, Sandia Peak Tramway and even hiking the Petroglyph National Monument.

During the wintertime on this Denver to Albuquerque road trip you can expect snow, especially at high elevations. Keep an eye on the weather and come well prepared for the drive.

Recommended by me – Nikki of Inspired Routes

2. The Oregon Coast (an underrated region on this list of winter road trips USA)

winter road trips USA view of snowy town with sign that reads NYE Beach

  • Distance: 364 miles
  • Recommended time: 4-5 days

If you’re looking to escape the snow for a bit, head to the Pacific Ocean and plan an  Oregon Coast road trip ! The entire route is on Highway 101, with 364 miles from Astoria to Brookings, Oregon.

The entire drive can be done in 7 hours, but it’s definitely recommended to spend your time seeing all the sights over a few days instead. Plan for the trip to take 4-5 days and to make plenty of stops throughout the day.

Driving along the Oregon Coast is a great place to enjoy a winter road trip, because the weather is great. There are rarely road closures because of snow!

Winter is also considered shoulder season on the coast . You may encounter more rainy days than sunny ones, but if you are prepared with some good rain gear, you’ll get a lot of popular beaches to yourself!

You will also be able to find plenty of affordable hotels and cabins along the coast. You’ll get the best deals on entry fees, accommodations, and travel costs in the winter season.

The Oregon Coast is special for a lot of reasons, but the biggest one is whale watching! During the months of December and January, you can spot whales making their annual migration south . Visit the OPRD Whale Watching Center in Depoe Bay for more information!

There are also lots of gorgeous hiking trails along the coast, and the winter season provides perfect peace and solitude from the crowds.

If you love the outdoors and are looking for ways to get outside this winter season, head over to the Pacific Northwest! It’ll surely be one of the best US winter road trips you’ll ever take!

Recommended by Emily of The Mandagies

3. Florida Keys (a favorite on this list of best road trips in winter)

two bridges leading to island in florida keys winter road trips USA

  • Distance: 165 miles
  • Recommended time: Minimum of a weekend and maximum of a week

One of the best winter road trips in the USA is a Florida Keys road trip from Miami to Key West. Not only is this drive stunning but it is best enjoyed in the winter when hurricane season is over. Plus, the daily highs are in the 70s F while daily lows are in the 50s F. 

To start, this route will take you from downtown Miami, where you can stop at the Perez Art Museum and Biscayne Bay National Park. This is a great place to go snorkeling since the park is free to enter and is covered by beautiful water. 

Next, continue to the Everglades and go on a fun airboat ride before heading to John Pennekamp Coral Reef State Park in Key Largo. H ere, you can do a bit of scuba diving among some of the only living coral in the country.

Take some time to explore the beautiful waters of Key Largo as you jet ski, kayak, and scuba dive through cool offshore wrecks. 

When you’re ready, continue your road trip and stop for lunch at Robbie’s Waterfront . This way you can feed the giant school of Tarpons here before learning about local wildlife at the Dolphin Research Center and the Turtle Hospital.

You can then get out and walk along the old 7-mile bridge before driving from the middle keys to the lower keys. 

End your trip in Key West where you can do a day trip to Dry Tortugas National Park, sample some Key Lime Pie, and explore the Ernest Hemingway Home.

Recommended by Victoria of Florida Trippers

4. Seattle to Leavenworth, Washington

winter road trips view of Leavenworth WA with cute downtown buildings decorated for Christmas

  • Distance: 117 miles
  • Recommended time: 3 days

If you’re looking for a wintery wonderland road trip, through pine trees and mountains covered in snow, make the two hour and 15 minute drive east from Seattle to Leavenworth, Washington.  You could obviously drive this all in one go, but the incredible alpine landscape is best savored. 

Make your first stop in the cute town of Skykomish, which is surrounded by Snoqualmie National Forest, home to some of the best snow-shoeing trails in the area!

Continuing on your journey, consider a stop at Scenic Hot Springs. They are a unique series of tubs with steamy water, tucked 2.2 miles up into the Cascade Mountains. The springs are on private property so you’ll need to book a permit to make the trek here well in advance. 

Next up, Stevens Pass Ski Resort is one of the most popular ski resorts in Washington, with an eye-popping 1,125 acres of skiable terrain. It offers something for beginners and advanced skiers and snowboarders alike, with 37 major runs and 10 chairlifts. 

Finally, your end destination during this road trip in the winter will be Leavenworth, a charming Bavarian-themed town that looks straight out of the  Sound of Music .

While Leavenworth is adorable all year round, it explodes with Christmas cheer in the wintertime, with over half a million Christmas lights festooning its downtown. And good news—even if you’re visiting past the holidays, the decorations here actually stay up through February!

While you’re here, book a stay at any of the Bavarian-style  hotels in Leavenworth , like the Bavarian Lodge or the Blue Elk Inn , so you can get cozy in the town and enjoy a steaming mug of  gluhwein  or two.

The mountains passes along the main road you’ll take, US 2, can get large amounts of snow in the wintertime and close in inclement weather.

Keep an eye on the Washington Department of Transportation website for closures and pack some tire chains in your ca r. They come in handy (and can even be legally required in some instances) when it’s particularly snowy out!

Recommended by Jess of Uprooted Traveler

5. New England (one of the best winter road trips in the Eastern US)

  • Distance: 465 miles (Round-trip to and from Boston)
  • Recommended time: 7+ days

While a snowy, winter road trip through the charming towns of New England may not be a popular one to take this time of the year, it’s most definitely a magical and cozy option!

Between tons of options for skiing, cozy inns, covered bridges, fantastic dining, and easy to navigate roads, it has everything for a wonderfully memorable road trip in the Northeast.

The best place to start any New England road trip, even in the winter, is Boston. This gorgeous city is worthy of a day or two on its own, but also offers the most flight options, and is centrally-located to many popular destinations.

Winter is the off-season in Boston, too, which means you’ll find some fantastic hotel rates!

Next, head off to Vermont, where you’ll find quaint villages and picturesque winter scenery at every turn. Stowe and Woodstock are the best towns to visit in  Vermont in the winter , and you’ll find great ski resorts here, adorable Main Streets, covered bridges, and winter activities during your visit.

Next, make your way over to New Hampshire’s White Mountains, where you can enjoy more world-class skiing, and book a stay at a cozy cabin or a homey inn. Take a sleigh ride or go ice skating at Nestlenook Farms in Jackson , ride The Cog to roast marshmallows on Mount Washington, and book a table at the lovely Christmas Farm Inn’s restaurant.

Lastly, make your way through Maine, where you can see some of the beautiful lighthouses in their off-season (and if you’re lucky, catch them after a gorgeous snowfall).

Maine is also home to some of the best breweries in New England (Portland has over 60 of them!). This is a great time of year to sample all the local brews while enjoying the spectacular coastline – which you’ll probably have all to yourself. 

End your time in Maine by visiting the coastal town of Kennebunkport, and book dinner and hand-crafted cocktails in a private fish shack at Batson River, which are decorated perfectly for winter on the inside. 

While New England does average about 90 inches of snow each winter, the roads are generally safe to drive on, as plows come through often . However, it’s a good idea to rent or drive a car with snow tires for added peace of mind during your road trip.

Recommended by Sam of New England Wanderlust

6. San Francisco to Lake Tahoe

skiing in Lake Tahoe down hill through trees view of best road trips in the winter

  • Distance: 200 miles
  • Recommended time: 2-3 nights

For anyone looking for a beautiful winter road trip through the mountains, this is for you! The route from San Francisco to Lake Tahoe takes you through the Sierra Nevada Mountains to end at Tahoe City , one of the major towns on the North Shore of Lake Tahoe.

The route travels exclusively along Highway I-80, which traverses from coast to coast through the northern states!

This route is perfect during winter because you will see the gorgeous snowfall once you start climbing the Sierra Nevada Mountains. The evergreen trees are something special when covered in snow and something everyone should see at least once!

Lake Tahoe is absolutely stunning when covered in snow, and there are so many  things to do in Tahoe in the winter !

Along the route, you will travel through Donner Pass, which is an infamous pass in the Sierra Nevada Mountains. It gets its name from the Donner Party, who tragically got stuck while traveling through the mountains by wagon. Donner Memorial State Park is located near the pass, and is worth a visit while on your trip.

When traveling from San Francisco to Lake Tahoe during winter months, it is important to be prepared for driving in the snow.

Although snow plows frequently plow the snow along the highway, there is tight regulation by rangers on who can go on the highway during snow storms to ensure the safety of all travelers. A car with 4-wheel drive or chains is often required on this route when there is snowfall, and the rangers will ensure all travelers have either before entering the Sierra Nevadas. 

Road closures can happen, and will be available to view on  Go Tahoe North . Road closures are typically only present during severe winter storms , with the road closure lasting anywhere from hours to days depending on the severity.

This route gets heavy traffic during the holidays, and on Friday afternoons as the Bay Area residents come to Tahoe for a weekend ski trip! To avoid traffic, plan to leave early in the day or during a weekday is possible.

Recommended by Jess of Travel + Tannins

More road trips in winter

Are you packing your winter coat or bathing suit for your winter road trip? Keep reading for more of the best US winter road trips!

7. Big Island of Hawaii (a perfect road trip in the winter for sunshine)

Onomea Falls big island hawaii view of water falling off mossy rocks in jungle landscape

  • Distance: 125 miles
  • Recommended time: 3+ nights

If you are looking for one of the best road trips in winter, then head to the Big Island of Hawaii.

This fun road trip starts in  downtown Hilo  and takes you around the island. Although you can do this in one day, I recommend spending at least 3 nights to fully appreciate the island. Staying overnight at any of the places along the way will make your visit and experience more impactful and fun without needing to rush.

The total distance around the island is about 125 miles or 3 hours in each direction . But you will definitely want to stop at many points along the way.

Start by driving down the Belt Road through the Hamakua coastline. Here, you can visit scenic roadways like the Onomea scenic drive. Be sure to save time for a stop at the beautiful Hawaii Tropical Bioreserve and Gardens.

Then, continue on to Akaka Falls. It’s one of the most striking waterfalls and natural garden to visit.

As you traverse along cliff roadways, you can stop by the western town of Honoka’a and then see the largest gluch area of Wapio Valley from the observation area lookout. 

Lunch can be in the Paniolo town of Waimea with some shopping fun at Parker Ranch or the many daily public markets in the area.

Continue down the belt road to Kona side and visit Waikoloa area and the gorgeous white sandy beaches in the area. Kona town is historic with a fun old downtown to explore. You’ll also find The Summer Palace and gorgeous stone church of Mokuaikaua.

You might want to stay overnight in Kona or you can continue on towards the Hawaii Volcanoes National Park. On your way down to the south of the island, be sure to visit the Green Sand beach or the Black Sand Beach at Punalu’u.

The national park is the biggest attraction of the island and can easily be a day trip on its own. You might want to consider an overnight stay to enjoy some hikes, vistas, visit to lava tubes and gorgeous fern forests in the park area.

After the national park, continue back towards Hilo to do more exploring in the old town and many lush gardens , waterfalls and fun outdoor activities and adventures.

Recommended by Noel of This Hawaii Life

8. Bryce to Capitol Reef via Escalante, Utah

road trips in the winter view of orange spires and rock valley with snow in Utah

  • Distance: 150 miles 
  • Recommended time: 4-6 hours

Southwestern Utah is a beautiful destination for a winter road trip. Most sights will be far less crowded, allowing you to visit the state’s finest landmarks in peace .

Winter temperatures range from 11°F to 38°F, which makes a warm car the best way to explore Utah during this season.

Take a scenic drive from Bryce Canyon to Capitol Reef via UT-12 for a winter wonderland road trip. This 150-mile road connects two national parks via Dixie and Fishlake National Forests . Budget at least 3.5 hours to complete the drive and another 1-2 hours to stop at the viewpoints. 

This route reaches a maximum elevation of 9,593 ft . Other than a few small patches of ice, the drive is accessible year round, and is one of the best routes for sightseeing during an Utah national parks road trip . It’s still a good idea to check the national park websites for road and attraction closures after heavy snowfall.

You will likely drive across a snowy landscape, which makes this one of the best road trips in the winter. Get ready to be mesmerized by Utah’s winter colors. Red rock, green pine trees, white snow, and blue sky are a combination to see. These views are sure to make this winter road trip a memorable adventure.

You should save about half a day to explore Bryce Canyon and Capitol Reef. You can enjoy the park overlooks right from your car. But pack snacks, layer up, wear sturdy shoes , and bring crampons if you plan on hiking. Be sure to take your Interagency pass to save on the entrance fees.

Recommended by Anastasia of Travel Realist

9. Niagara Falls to New York City (one of the best winter road trips USA)

winter road trips with view of NYC skyline and bridge with water in foreground

  • Distance: 410 miles

One of the best winter road trips to do on the east coast is from one of the biggest natural attractions to one of the biggest cities in the world. This Niagara Falls to New York City road trip is one of a kind.

There is a beautiful scenic road from the Niagara Falls, to Buffalo, Syracuse to New York. The route is known for its stunning scenery, with picturesque views on the vast forests, and charming small towns.

It snows a lot in this region and the temperature in winter ranges from 20° to 35°F. In fact, Syracuse is one of the snowiest cities in the United States . It creates a white winter fairytale that becomes especially magical at the Niagara Falls, the starting point of the road trip. 

Then, visitors can head east to Syracuse and the Ithaca area. There are stunning parks and waterfalls in this region and you should explore it for one or two days. Taughannock Falls State Park and Buttermilk Falls State Park become frozen wonderlands in winter.

If you want to visit a third park before reaching New York, Harriman State Park offers stunning hikes and has beautiful lakes. 

Last but not least, New York in winter is wonderful to experience the festive atmosphere. You could see a snowy Central Park, enjoy seasonal Christmas shows and even sleep in a skyscraper in Midtown Manhattan which is the  best area to stay in New York for first-timers .

Recommended by Soline of On The Road Diary

10. Phoenix to Page, Arizona

wavy slot canyon with orange walls in Antelope Canyon Arizona

  • Distance: 273 Miles
  • Recommended time: 2-3 Days

One of the best road trips in winter is from Phoenix to Page Arizona. While Phoenix and Page are less than 300 miles apart, there are a few great stops between them.

In fact, you pass directly through two of my favorite towns in Arizona – Sedona and Flagstaff. The  best of Phoenix  includes museums and outdoor activities so spend some time there if you can.

For the best road trip itinerary, I recommend spending one night in Sedona on your way up. While in Sedona be sure to take a Pink Jeep tour of the red rocks area to admire the scenic views and unique terrain.

Between Sedona and Page, stop in Flagstaff for a half day. It’s a great stop for lunch while being surrounded by the amazing alpine scenery.

Then, spend one or two nights in Page, depending on your schedule. Some of the  best things to do in Page  are hiking and outdoor adventure tours. Two must-see sights in Page are Antelope Canyon and Horseshoe Bend.

To see Antelope Canyon, you must take a tour due to local regulations. However, it’s well worth the time and money to see these iconic slot canyons. Horseshoe Bend is a quick hike that takes around 1 hour total.

Many people think of Arizona as a hot desert state. While that is true for places like Scottsdale and Phoenix, the north of Arizona is quite different.

Winter temperatures in Sedona, Flagstaff, and Page are often in the 30’s – 40’s. There’s even a ski area in Flagstaff!

Overall, a winter road trip from Phoenix to Page is guaranteed to be super scenic and will show you the diversity of the state’s geography. 

Recommended by Lauren of The Traveling Moore

11. Highway 30A, Florida (one of the warmest and best road trips in winter)

road trips in winter view of Panama City 30a with teal water white waves and city in distance

  • Distance: 24 miles 
  • Recommended time: 2 to 6 hours 

One of the most fun road trips in the Florida Panhandle is taking a drive along Scenic Highway 30A in South Walton County. 

The winter is a perfect time to visit since it’s the slow season. You can expect temperatures in the low 60’s for a high and 40’s for a low in the winter months.  

This stretch of highway is located on the backroads between Destin and Panama City Beach and winds along the Gulf Coast.   Start by visiting Topsail Hill Preserve State Park which is in Santa Rosa Beach , and has several walking trails and a secluded beach area. 

If state parks are your thing, then you’ll also want to visit Grayton Beach State Park and Point Washington State Forest, both on or near 30A. 

While in Santa Rosa Beach, visit Gulf Place, Ed Walline Beach Access, and Dune Allen Beach.  

As you make your way east, recommended stops are Blue Mountain Beach and the Blue Mountain Beach Creamery.  If you love seafood, grab a lobster roll at Chiringo in Grayton Beach.  There’s also the popular Red Bar and AJ’s nearby. 

Arguably, the most iconic part of 30A is  Seaside, Florida , where you take a step back in time in this slow beach town.  

You can’t miss Airstream Row food trucks since they’re located on 30A as you enter Seaside.  From here, you’re right by the town square, shops, waterfront restaurants, and the Van Ness Butler Beach!

Seaside is most known for being the place where the Jim Carrey movie, The Truman Show, was filmed.

Recommended by Wayne of Always on the Shore

12. Las Vegas to Zion National Park

winter road trips in the USA view of road through red rocky cliffs

  • Distance:  151 miles (2 hours if driving non stop)
  • Recommended time:  4 days

Las Vegas to Zion National Park is a great short (and safe) road trip to take in winter as the roads are in good condition, even if it snows . You would not expect road closures along this route as it follows major highways (Interstate 15 then Highway 9).

While you can technically make this trip in a day and it’s even one of the best day trips from Las Vegas . However, it would certainly be a mistake to only spend one day in Zion , as it is one of the best national parks in the USA!

There are also some great stops to make along the way including the very photogenic Valley of Fire State Park, Lake Mead and Toquerville Falls. If you are traveling with friends or as a couple, you can also make an overnight stop in the town of Mesquite Nevada which is a mini Vegas in the desert.

Winter is a  great time to visit Zion National Park  as there are way less crowds and still lots of fun activities to do! You can still hike the popular Angel’s Landing in winter, provided there is no snow.

Hiking the Narrows is also a possibility in winter with appropriate gear including a dry suit. Alternatively, you can do the easy and quick Canyon Overlook Trail , which has amazing views for less effort.

Expect the weather to be cold with a possibility of snow. Winter in Vegas reaches lows of 28 °F . You can expect Zion to reach a few degrees lower as it is located at a higher altitude.

Recommended by Bett of Utah Vacationers

Road trips in the winter continued…

In case you haven’t decided where to road trip this winter yet, here are more options – whether you’re seeking sunny weather or perfect ski conditions.

13. Albuquerque to Taos, New Mexico (an underrated winter road trip for ski-enthusiasts)

southwest architecture on building on an American road trip through the southwest over wintertime

  • Distance: 266 miles 
  • Recommended time: 5-7 days

Traveling through New Mexico is magical during the winter! One of the ideal routes starts in Albuquerque, the state’s largest city with biggest airport, heading north on the iconic Turquoise Trail (State Route 14).

This scenic highway leads travelers through historic mining towns and the picturesque Sandia Mountains.

Spend a few days in  Santa Fe , the state’s capital and primary tourism destination (1 hour from Albuquerque). You can explore art galleries, museums, and the historic adobe architecture of the city . The Old Town is walkable.

The winter season brings a unique charm to the city, with holiday markets like the Santa Fe Indian Market Winter Showcase and the Canyon Road Farolito Walk, where thousands of luminarias (paper lanterns) light up in the streets on Christmas Eve. To warm up on chilly winter days, get a bowl of the famous Green Chile stew, a Santa Fe specialty.

Continue further north to Taos Ski Valley, which is an hour and a half from Santa Fe. You’ll find wintery white slopes, and offerings for skiers of all levels. Visitors can also enjoy snowboarding, snowshoeing, and relaxing in hot springs like the famous Ojo Caliente Mineral Springs Resort & Spa.

Travelers should be prepared for winter weather in New Mexico, which can vary from mild to cold temperatures, especially in the high-altitude regions. The daily temperature in winter in Santa Fe is 48 degrees.

From December to February, snowfall is common, making road conditions unpredictable. Check weather forecasts and road conditions regularly, as occasional road closures can occur due to snowstorms, especially in the Taos Valley.

If flying back home, travel back to the Albuquerque Airport to complete your journey.

Recommended by Eleanor of Elevate Your Escapes

14. Lincoln to Conway, New Hampshire

waterfall in snowy mountain scene during a winter road trip through New Hampshire

  • Distance: 34 miles
  • Recommended time: 1-2 days

If you’re looking for a picturesque winter road trip destination, look no further than New Hampshire. The state has  charming New England towns  straight out of a Hallmark movie as well as stunning four-season mountain scenery. 

One of the best ways to experience this natural beauty is by taking a road trip along the Kangamangus Highway. 

Start your road trip along the Kangamangus Highway, a 34 mile stretch of road through New Hampshire that offers stunning views of the White Mountains . I’d suggest starting in Lincoln and taking the highway to Conway for optimal views.

The highway will remain open in the winter but be sure to keep an eye on the weather. I’d also suggest 4-wheel drive on your vehicle . Always drive prepared with water and blankets in case of an unexpected breakdown. 

Take the Kangamangus Highway to the town of North Conway. This charming town is known for its quaint storefronts, delicious restaurants, and outdoor activities .

Outdoor activities such as skiing, snowboarding, and even four-season fun can be found in North Conway making it an ideal destination for adventurers.

It was named one of the Top 10 Best Small Towns in America for Adventure, offering an exciting winter ski scene. There are six mountain resorts providing state-of-the-art lifts and trail grooming.

This road trip is perfect for those who want to view a combination of quaint towns and stunning snowy scenery.

Temperatures will be quite cold in the winter from 40-10 degrees Fahrenheit so make sure you are prepared. Winter (as well as fall) is considered high season in New Hampshire so make any hotel bookings well in advance.

Recommended by Sierra of Your Guide to Wandering

15. California deserts

best US winter road trips with view of crazy mountains in orange brown and mustard colors

  • Distance: 880 miles
  • Recommended time: 6 days

If you are looking to do a winter road trip in the western part of the country, consider a  California deserts road trip ! Starting and ending in Los Angeles, this road trip offers balmy weather, sunny skies, and some of the most majestic landscapes in the USA.

Fly into Los Angeles, pick up your rental car, and get ready to be wowed as you head first to Death Valley National Park, the hottest and driest place in the country. Spend a full day exploring the many sights here.

Then drive through the starkly beautiful Mojave National Preserve to California’s other great desert national park, Joshua Tree, which actually straddles two deserts.

Next, take a city break in Palm Springs, with its mid-century modern architecture and great eateries.

Then drive to Borrego Springs, where you will explore Anza-Borrego Desert State Park, which features oases and badlands. Finally, return to LA!

You’ll find great weather along this route in the winter, with daytime highs in the 60s and 70s. Nights will get cold, though, so bring layers if you want to gaze at the night skies!

Roads are usually open along this route in the winter, but you’ll want to check right before you go. Bring sun protection and remember to stay hydrated during this epic winter road trip in the US!

Recommended by Dhara of Roadtripping California

16. Denver to Glenwood Springs, Colorado (another favorite on this list of best US winter road trips)

snowy mountain with skier and blue sky

  • Distance: 157 Miles
  • Recommended Time : 6 hours with stops

In the heart of the Rocky Mountains, you will find one of the most gorgeous road trips in winter in the US. The popular route connecting Denver, CO to Glenwood Springs, CO takes travelers on a magical journey on I-70 passing through mountain towns, ski resorts, and jaw-dropping scenery.

Along the route, you will find many amazing points of interest including the world-famous Red Rock Ampitheater, Loveland Pass Viewpoint, Frisco, CO, and multiple ski resorts.

Just off the interstate, you will find Copper Mountain Ski Resort , known for its massive Superpipe that you can see right off I-70!

Additionally, this drive is home to one of the most beautiful stretches of highway in America, the Glenwood Canyon. This picture-perfect 12.5-mile stretch of road weaves travelers through a canyon following the Colorado River.

During the winter months, this drive turns into a winter wonderland. This means it can become very dangerous, so having the proper equipment and tires for your car is importan t. In fact, sometimes it’s even closed due to the weather!

When driving this route in winter, it is important to be flexible with the weather and drive safely. The drive from Denver, CO to Glenwood Springs, CO takes drivers through some of the most spectacular mountain scenery with many fun stops along the way.

Recommended by Danika of Destination Danika

17. Fort Pierce to Fort Lauderdale, Florida

view of lifeguard stand and palm trees on beach at sunset in Florida

  • Distance: 110 miles
  • Recommended time: at least one weekend.

Driving from Fort Pierce to Fort Lauderdale, Florida is undoubtedly one of the best winter road trips USA for travelers to explore. This route is considered to be one of the best routes during winter for two main reasons.

Firstly, you will be driving through some of the  warmest places in Florida , featuring warm and mild temperatures and sunshine, ranging from 62 to 81 degrees . This makes it the perfect escape from the chilly weather of northern states.

Secondly, there are several interesting stops along the way – both manmade and natural – that are worth exploring.

The quiet shores of Hutchinson Island are the perfect place to have the beach all to yourself. Soft sand, lush palms, and blue ocean stretch for miles.

The Riviera Marina at Palm Beach is a great place for snorkeling and stand up paddleboarding, for anyone looking for fun water sports. You can even paddleboard to small islands and islets off the shore!

Also on the way is Boca Raton, a city known for its golf courses, green parks and beaches. Animal enthusiasts will find a butterfly garden and a sea turtle sanctuary here, too . Downtown is the well known Boca Raton Museum of Art, with modern and contemporary collections for the art lovers.

Once you reach Fort Lauderdale, a lot of exciting venues await. Plentiful museums and an active nightlife grace the city of Fort Lauderdale.

One important thing to note while traveling during this period is that it gets dark quite early, so it’s essential to plan accordingly. Be sure to start all water activities well before sunset.

Overall, driving from Fort Pierce to Fort Lauderdale Florida during winter is a fantastic choice, with the striking landscapes along the route making the trip even more memorable.

Recommended by Monica from This Rare Earth

Winter road trips recap

vivid color lake with trees and snowy covered rocks and mountains in distance

Gah! So many good options, right?! Whether you’re looking to keep those Vitamin D levels in check or seeking outdoor activities with brisk air, there’s so many great routes to take during the best US winter road trips.

From Florida to New England, Utah to Oregon, the possibilities seem endless when it comes to adventure in the winter months in the USA.

Here’s a quick recap of the best winter road trips in the US!

Best road trips in winter

  • Denver to Albuquerque
  • The Oregon Coast
  • Florida Keys
  • Seattle to Leavenworth, Washington
  • New England
  • San Francisco to Lake Tahoe, California
  • Big Island of Hawaii
  • Bryce to Capitol Reef via Escalante, Utah
  • Niagara Falls to New York City
  • Phoenix to Page, Arizona
  • Highway 30A, Florida
  • Las Vegas to Zion National Park
  • Albuquerque to Taos, New Mexico
  • Lincoln to Conway, New Hampshire
  • California deserts
  • Denver to Glenwood Springs, Colorado
  • Fort Pierce to Fort Lauderdale, Florida

Related posts to read next: 29 Amazing Road Trips USA: Scenic (& Underrated) Routes You’ll Love 30 Gorgeous West Coast Road Trip Routes You Gotta See to Believe 26 Absolute Best (and Underrated) Fall Drives in the US You’ve Gotta See to Believe 23 Incredible RV Vacations: Scenic RV Road Trips You Need to Take

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17 exciting winter USA road trips with 3 photos of snowy and beach destinations

Saturday 25th of November 2023

So many amazing suggestions on here! Bryce Canyon has been on my list for the longest time - looks stunning with a bit of snow. Also, stunning photos 😍

Friday 1st of December 2023

Oh yay Haylee! Sounds like a trip to Bryce Canyon National Park is in your future. It's one of my favorites on this list for sure!

Saturday 18th of November 2023

What a great variety of road trips you've covered. Coming from New England, id choose the Florida trip.

Tuesday 21st of November 2023

Great choice Amy! Gotta love that sunshine and warm weather during the wintertime 🏖️

This is an amazing collection of road trips. I'd love to do them all in time!

Oh yay Sara! Glad you found some inspiration here :)

New England Scores

  • Boston Bruins

Berkshire Bank Hockey Night In New England: Projected Bruins-Kraken Lines, Pairings

Boston concludes its four-game road trip in seattle.

The Boston Bruins wrap up their four-game road trip against the Seattle Kraken at Climate Pledge Arena on Monday night.

Boston has needed overtime in five consecutive contests, the previous two concluded as overtime losses for the Black and Gold. Meanwhile, the Kraken are coming off a loss to the Minnesota Wild on Saturday.

Kevin Shattenkirk and Parker Wotherspoon will play alongside one another on Boston’s third pairing. Derek Forbort won’t play Monday after missing a team meeting.

Anthony Richard will get the chance to play on the Charlie Coyle line with Brad Marchand on the opposite wing.

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Puck drop from Seattle is scheduled for 10 p.m. ET. You can watch it live on NESN after an hour of pregame coverage.

Final Score

Check out the lines and pairings of both teams here .

BOSTON BRUINS (34-12-13) Brad Marchand — Charlie Coyle — Anthony Richard Jake DeBrusk — Pavel Zacha — David Pastrnak Danton Heinen — Morgan Geekie — Trent Frederic James van Riemsdyk — Jesper Boqvist — Justin Brazeau

Matt Grzelcyk — Charlie McAvoy Mason Lohrei — Brandon Carlo Kevin Shattenkirk — Parker Wotherspoon

Linus Ullmark

SEATTLE KRAKEN (24-22-11) Jared McCann — Matty Beniers — Jordan Eberle Jaden Schwartz — Alex Wennberg — Oliver Bjorkstrand Eeli Tolvanen — Yanni Gourde — Andre Burakovsky Tomas Tatar — Kailer Yamamoto — Brandon Tanev

Vince Dunn — Adam Larsson Jamie Oleksiak — Will Borgen Brian Dumoulin — Justin Schultz

Philipp Grubauer

Presented by Berkshire Bank, the official bank of NESN’s Boston Bruins coverage.

About the Author

winter road trips in new england

Sean T. McGuire @BySeanMcGuire

Digital Content Producer for NESN.com

One half of the NESN.com media boys. Bill Belichick once told me I asked a "Good question," and I think he meant it. Then again, a social media stranger once hated me for trashing Tua Tagovailoa.

In This Article

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  • Hockey Night in New England

Featured image via Brian Fluharty/USA TODAY Sports Images

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IMAGES

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COMMENTS

  1. 21 Best New England Winter Getaways (Even For Non-Skiers!) 2023-2024

    Even if you don't ski, there's so much to do in the winter in New England, including ice skating, fireside dinners, relaxing spas, snow tubing, scenic drives, and sampling all the seasonal flavors in some of the best restaurants in the Northeast.

  2. Best 5 New England Winter Drives

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  3. 23 Coziest New England Winter Getaways to Take in 2024

    The Best Winter Getaways in New England 1. Newport, Rhode Island 2. Burlington, Vermont 3. Rangeley, Maine 4. Boston, Massachusetts 5. Stowe, Vermont 6. Westerly, Rhode Island 7. Hartford, Connecticut 8. North Conway, New Hampshire 9. Nashoba Valley Ski Area, Massachusetts 10. York, Maine 11. Manchester, Vermont

  4. EPIC New England Road Trip Itineraries (2024)

    Winters are long and can be bitter cold and summers feel unfairly humid and short. Winter will complicate driving conditions - but the views will be extraordinary. The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

  5. The Flexible New England Road Trip Itinerary You Need in 2024 ️

    Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list.

  6. 10 Road Trips That You Can Take Through Snow-Covered Mountains In New

    Scenic wintertime road trips through New England offer the perfect opportunity to experience the tranquility and beauty of a fresh snowfall and stunning vistas. Travelers can immerse themselves in ...

  7. The Ultimate New England Road Trip Itinerary (Updated 2023)

    From coastal cities and towns to mountain resorts, New England is the perfect place for road trips. Once the cold weather is behind us, Bostonians like myself set out for day trips, weekend getaways, and even multi-week road trips to see all this region has to offer.

  8. New England has one of America's top winter road trips, according to

    November 4, 2020 A rural route in New England full of quaint country stores and plenty of natural beauty was recently named a top winter road trip in America by Travel + Leisure magazine....

  9. 16 New England Winter Getaways

    For history buffs, the historical landmarks along the Freedom Trail are a must-see on your winter road trip itinerary. Interested in some day trips in New England in the winter? A rental van offers the chance to visit Cambridge, home to Harvard University, and spooky Salem, known for the famous witch trials.

  10. The Ultimate 10-Day New England Road Trip Itinerary

    This New England road trip itinerary visits Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island and captures as much of New England's charm, beauty, history and quirkiness as possible in ten days - with plenty of stops for witches, ghosts, and lobsters along the way. Take it away, Anna! Table of Contents

  11. 5 Must-Do Adventures On Your Winter Road Trip Through New England

    5 Must-Do Adventures On Your Winter Road Trip Through New England Escape the city and hit the road. By: Chris Mongeau + Save to a List Winter in New England can be brutal, and while this year hasn't exactly been the worst, it's still early March and there's a very good chance we could get hit with more snow and cold spells again.

  12. 9 Best New England Road Trips to Take Throughout the Year

    Whether it's spring, summer, fall, or winter, there's a road trip (or two) for each season. View of Horsehead-Marbella, an historic house near Beavertail State Park. Photo by Trevor Fairbank/Shutterstock New England may be known for its autumn reds and yellows, but to us, there's no bad time to cross the region by car.

  13. 71 BEST Tips New England Winter Road Trip (Selected)

    New England Winter Trip Winter in New England is a magical time of year. With its picturesque landscapes, charming towns, and abundance of outdoor activities, this region offers a unique and unforgettable winter experience. ... 71 BEST Tips New England Winter Road Trip (Selected) Jan 10, 2024. 0 People Read. Table of Contents. New England ...

  14. The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options

    Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, Vermont · November 8, 2022 The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options!) 2024

  15. New England Winter Road Trip

    NEW ENGLAND WINTER ROAD TRIP STRATTONKILLINGTON RESORTSUGARBUSH RESORTLOON MOUNTAINSUNDAY RIVERSUGARLOAF Take a trip to New England for access to one of the planet's most highly saturated skiing and riding areas —including six Ikon Pass destinations all within five hours of each other.

  16. Guided Winter Adventures in New England

    Guided Winter Adventures in New England. From snowshoeing rolling trails to riding horseback through the woods, let a professional guide show you the best of a New England winter. By Yankee Magazine. Dec 20 2018. Summiting New England's highest mountain might be the ultimate winter adventure, but it's not to be undertaken lightly.

  17. Road-Tripping New England: My Suggested Itinerary

    Days 10-12: Moosehead Lake, ME. Moosehead Lake is just 2.5 hours north of Bangor. It's the second-largest lake in New England and the largest in the state. Spanning over 75,000 acres, it's perfect for fishing, boating, hiking, and relaxing. You can rent a boat or jet-ski, camp, or stay at one of the lodges.

  18. New England Winter Road Trip

    New England is a great road trip destination, since the states are so compact and close together. Plus during the winter, the roads are not scary like other parts of the US that get snow. Day 1 of our New England Winter Road Trip: We flew into Boston and was supposed to arrive around 11am, but unfortunately we had a flight delay.

  19. 12 Day New England Road Trip Itinerary

    7 A.M. Drive to Stonington. Start the day early with a 2-hour drive from Camden to Stonington. This is the town where Isle au Haut Boat Services offers trips to and from Isle au Haut. Year round this ferry takes visitors to Isle au Haut town, a small settlement on the north of the island.

  20. The Ultimate 10-Day New England Road Trip Itinerary

    Salem, Massachusetts & Portland, Maine (Day 2) Salem, Massachusetts. Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you'll drive for about 40 minutes to reach Salem.

  21. The Ultimate New England Road Trip Itinerary

    Last updated on February 9, 2024 New England exceeded all expectations. It was my small-town Gilmore Girls dream brought to life - I'm not sure I've ever used the word "charming" quite so often. Plus the nature blew my mind. From Acadia to the White Mountains to the forests and lakes of Vermont, every state has something spectacular to offer.

  22. 47 Fabulous Day Trips in New England

    September 24, 2022 by Jamie Italiane Whatever season you are visiting, New England has many spots perfect for day trips. We have green forested mountains, rocky coastlines, colonial history, and extraordinary seafood. If you plan a New England road trip, this New England day trip guide can help you plan where you should visit.

  23. The Best Time To Visit New England In 2024 + A Month By Month Guide

    Driving around New England in the winter is also a concern, but generally, ... The BEST 7 Day New England Road Trip Itinerary (Plus 5 & 10 Day Options) Best New England Resorts & Spas;

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    Passing right through Acadia National Park on Mount Desert Island, Park Loop Road takes visitors on a 3-hour-long trip through the park's most scenic route and most popular attractions to be found ...

  25. 17 Exciting Winter Road Trips USA: Scenic and Unexpected Routes You'll Love

    This list of the best road trips in winter takes you on routes like through quaint snowy New England towns or the sunny Florida beaches. Whether you love skiing and winter hikes or desert landscapes and palm trees, this list has something for everyone! Must-see video: winter road trips Map of road trips in winter

  26. Hockey Night In New England: Projected Bruins-Kraken Lines, Pairings

    The Boston Bruins wrap up their four-game road trip against the Seattle Kraken at Climate Pledge Arena on Monday night. Boston has needed overtime in five consecutive contests, the previous two ...