best towns to visit in westchester ny

• Westchester County Points of Interest

Towns in Westchester County: Top 8 Most Unique Spots

• October 8, 2023

There are so many incredible places to see near Greenwich, you’ll hardly know where to start! Find more towns in Westchester County and beyond by downloading our free Greenwich, CT Vacation Guide!

8 of the Best Towns in Westchester County to Visit

Just a short drive from Greenwich, you’ll find a wide variety of fascinating towns to explore in Westchester County. Here are just a few of the most popular among our guests that we’re sure you’ll love as well!

White Plains

Also known as the commercial hub of Westchester, White Plains, NY is an affluent suburban community. Many visitors travel to this town to take advantage of the fantastic restaurants and shopping opportunities. In fact, the downtown area of White Plains offers a variety of shopping districts and malls filled with well-known New York-based stores. From high-end brands to affordable souvenirs and merchandise, you’ll find it all!

Formerly known as the village of Rye, New York , this charming waterside town received its official charter as a city in 1942. Since then, it has seen a variety of visitors who are eager to discover the rich history of the area. Rye sits on the National Register of Historic Places and is also home to an Art-Deco style amusement park and the popular Rye Playland . You’re sure to love the abundance of things to do including ice skating, thrilling rides, lounging on the beach, and much more!

Sleepy Hollow

Yes, this town does not just exist in the folk legend. It is a very quaint village located about 30 miles north of New York City. Here, you’ll find the Rockefeller State Park Preserve , a lovely wooded hiking trail with many examples of varied habitats. If you wander into the famous cemetery of Sleepy Hollow , you’ll find the graves of influential figures in American history including Washington Irving and Andrew Carnegie. Do you find it a coincidence that this tiny town is known as one of the most haunted places in America considering it is presumably the setting for one of America’s most chilling legends.

Just south of Sleepy Hollow, Tarrytown is not as famous as its neighboring village. But there are plenty of attractions, activities, and things to do in Tarrytown, NY , throughout the year, not just in the Halloween season. The main street feels like a Norman Rockwell painting, with a much more diverse dining scene. And the parks in the hills overlooking town and down by the Hudson River are splendid.

Waccabuc, New York is a hamlet and lake town near Lewisboro. It is commonly known by the locals as “New York’s secret suburb” and houses a collection of privacy-loving C.E.O’s and bright stars. Despite is quiet and laid-back atmosphere, there are many things to do! Visitors come to Waccabuc to see the stunning real estate and Castle Rock , a popular cliff jumping destination.

City Island

This unique little island hamlet isn’t part of Westchester County anymore. It seceded from the county and joined New York City in 1898. But it’s just off the coast of the Bronx and Westchester County. And a summertime visit to the City Island neighborhood is a shorter (and cheaper) trip for a quaint New England fishing village vibe.

Croton-on-Hudson

Most people just pass through the Croton train station, but there’s more here to explore than just that. The most historic of the things to do in Croton-on-Hudson, NY , is visiting Cortlandt Manor, especially in the fall for the Great Jack O’Lantern Blaze.

The original center of American filmmaking, Mamaroneck is still an artistic center. It’s still the home of Archie Comics. But its clusters of historic villages and verdant landscapes along the peaceful waterfront of Long Island Sound is a draw in an of itself. Some of the more unique spots to visit in Mamaroneck include the Skinny House, and, of course, the waterfront parks. And the village of Larchmont, NY , has a distinctly French feel, thanks to the staff at the French-American School of New York.

Pound Ridge

Up in the Northwest corner of Westchester County, the town of Pound Ridge, NY , is famous for its rolling hills and woods. Meaning: not a lot of people here. But there does appear to be a high concentration of celebrities, and the hiking trails at Ward Pound Ridge Reservation and other parks is splendid. Plus, you can score a NYC-level meal at the Inn at Pound Ridge, or work on your swing at the Pound Ridge Golf Club.

Return to Stanton House Inn for the Ultimate Greenwich, CT Experience

After exploring the various towns of Westchester County, we invite you to come back and enjoy the enchantment of Greenwich in our historic inn. From here, you’ll be able to reach the best Fairfield County destinations and the most cute towns in Connecticut , as well.

Recognized as one of the most romantic bed and breakfasts in Connecticut, The Stanton House Inn is a destination for couples. Our beautiful guest rooms exude historic charm while the rest of the inn warmly welcomes visitors with lovely decor and tranquil ambiance. Don’t forget to take advantage of our inn’s exclusive vacation packages and extras ! Book your stay at the Stanton House Inn today and we look forward to welcoming you soon!

Updated and republished: October 8, 2023

Related posts:

Leave a Reply Cancel Reply

Your email address will not be published. Required fields are marked *

Name  *

Email  *

Add Comment  *

Save my name, email, and website in this browser for the next time I comment.

I accept the Privacy Policy *

Post Comment

Westchester County

Located just north of New York City on the East bank of the Hudson River, Westchester County is an easy trip by train or by car.  The Historic Hudson River Towns along Westchester’s Hudson shore offer travelers charming downtowns with antique shops, art galleries and restaurants galore. Visitors can explore historic sites that tell stories of days gone by, from colonial America, to the homes of author Washington Irving, industrialist Jay Gould and the Rockefeller family. The riverfront always beckons with delighful spots for walks and picnics, while hiking, sailing and kayaking provide outdoor adventures for all ages. Plenty of cultural experiences, such as art museums and performing arts , will thrill and delight visitors. Member communities in Westchester stretch from Yonkers to Peekskill , many  with train depots and all with Main Streets to explore. Come visit Westchester County, close to New York City while serving as the gateway to the Hudson Valley.

Briarcliff Manor

The hilly, tree-lined streets of this thriving village, which occupies 70 percent of the combined areas of Ossining and Mount Pleasant, are dotted with the mansions of millionaires who came to the village after the turn of the century. Some are still privately owned but many have been subdivided into housing developments.

Briarcliff Manor was the vision of Walter Law, who in 1890 retired from the carpet business and moved to what was...

The Village of Buchanan is located in the northwestern corner of Westchester County on the eastern bank of the Hudson River, 20 miles north of White Plains. The Village is part of the Town of Cortlandt.

Many village residents are employees of the Indian Point Power plant, now owned and operated by Entergy Corporation, an integrated energy company engaged primarily in electric power production, retail distribution operations, energy...

One of the largest municipalities in Westchester County, The Town of Cortlandt encompasses two incorporated villages, several hamlets and even more neighborhoods. Each has distinctive characteristics, but they are united by their magnificent common heritage. The town, boasting almost 15 miles of Hudson River shoreline, extends from the Bear Mountain Bridge in the north to the Croton River. The City of Peekskill and Town of Yorktown borders...

Croton-On-Hudson

The Village of Croton-on-Hudson has a history of welcoming a diversity of newcomers to its almost five square miles set between the Hudson and Croton Rivers. Kitchawanc Native Americans are supposed to have greeted Henry Hudson himself on the shores of Croton Point, and later allowed the Tellers, one of the first European families to arrive, to farm on the promontory.

The Van Cortlandt family, whose Manor House is open regularly to...

Dobbs Ferry

Called a typical Hudson River village, Dobbs Ferry is unspoiled by tract homes and shopping malls, retaining the quaint flavor of an American small-town. The village offers visitors the chance to walk amidst breath-taking views of the lower Hudson River and the Palisades on the river's western banks. Walking tours of historic and architecturally interesting homes and buildings are offered, many highlighting the unusually rich collection of...

Hastings-On-Hudson

Were it not for the spectacular view of the George Washington Bridge spanning the Hudson River with the Manhattan skyline backdrop, one would find it hard to believe that the charming village of Hastings-on-Hudson was a mere half hour train ride to Grand Central Station.

The Village has a fascinating history with many distinguished artists, performers, writers and scholars who contributed to its cultural past and present. Among its...

The New York Times once wrote, "Irvington is the kind of village, that when you sneeze, 50 people will say 'bless you.'" This caring and welcoming attitude has drawn residents, including many well-known stars of stage, screen, television and radio, and tourists alike.

From its quaint shops to its beautiful homes and spectacular Hudson River views, Irvington is a classic example of the best of the Historic Hudson River Towns....

Mt. Pleasant

The Town of Mount Pleasant is located in central Westchester County, New York approximately thirty miles north of New York City. It is bounded on the north by the Towns of New Castle and Ossining, on the south by the Town of Greenburgh, on the east by the Kensico Reservoir and the Town of North Castle and on the west by the Hudson River. Within its boundaries lie the incorporated villages of Pleasantville, Sleepy Hollow, and a small portion...

The Town and Village of Ossining comprise one diverse community built on rolling hills overlooking the Hudson River. The community, originally named Sing Sing after the native American Sint Sinck tribe, was renamed Ossining in 1901 to distinguish the community from the Sing Sing Prison, after a boycott of prison-made goods hurt businesses in the town.

Still the site of Sing Sing Prison, Ossining boasts a crescent of 19th Century...

The glorious views of the Hudson Highlands from the City of Peekskill emphasize its strong relationship with the history of the nation. George Washington considered the area a strategic key to the defense of the nation. He established headquarters at the Birdsall House and there, against his better judgment, signed Benedict Arnold's command of West Point. Peekskill was razed twice by the British during the Revolutionary War, and some of the...

Sleepy Hollow

A visit to the village of Sleepy Hollow takes you directly to the area made famous by author Washington Irving. It is here you'll find the Old Dutch Church, the Sleepy Hollow Cemetery and nearby Pocantico River, brought to life in literature by Ichabod Crane's legendary encounter with the Headless Horseman.

Experience the beauty of the Hudson River with a stroll through Kingsland Point Park, where visitors can also see the historic...

A trip to Tarrytown offers visitors the perfect complement of history, dining, shopping and nature -- not to mention entertainment and first class lodging. From the majestic Hudson River views, including the Tappan Zee Bridge, to its Historic Districts showcasing 19th and 20th century architecture to its many unique shops and fine restaurants and hotels, Tarrytown offers something for everyone.

It was in Tarrytown that America's first...

The largest city in Westchester County, Yonkers offers visitors the best of all worlds. From its major shopping district along Central Avenue to the peace and tranquility of the Lenoir Nature Preserve, Yonkers has something for everyone.

The Hudson River Museum of Westchester is one of the county's jewels, offering historical and environmental displays and learning centers as well as the county's only planetarium. A highlight in the...

Things to Do

Westchester County is the heart of New York, with a variety of amazing destinations that includes grand Rockefeller properties, well-preserved 18th-century homesteads and picturesque farming villages that dot the countryside. Plus, our shows, fairs and festivals are second to none – from the annual Riverfest summertime celebration showcasing Yonkers' redone waterfront to top productions staged throughout the year at a variety of performing arts centers.

The county offers year-round fun, but with a serious side that lets you get down to business. After all, Westchester is "New York's Intellectual Capital", where a highly educated workforce resides and constant inspiration comes from world-renowned colleges, universities and research centers. Here, among our variety of attractions, meeting spaces and accommodations, you can be productive and still play hard, too!

Although "the city" often refers to New York, Westchester boasts "the cities" –  New Rochelle ,  Yonkers  and especially  White Plains , the county's commercial and cultural hub. They each offer their own urban vibe, with culture and nightlife in abundance.

Westchester is for everyone with many resources for travelers with disabilities . For the kid in all of us, Westchester is home to  Playland , a Long Island Sound amusement park with family-friendly entertainment. Fun for LEGO fans young and old,  LEGOLAND Discovery Center  in Yonkers is an interactive world where kids can let their imagination run wild with creative inspiration at every turn. At the other end of the county – and the energy spectrum – Westchester is also home to Bedford, a picturesque Colonial town with quaint boutiques set amid rolling estates with celebrity residents.

There's So Much To Do

Check out some of our other highlights:.

Chic Shopping

In White Plains,  The Westchester  satisfies even the most discerning fashionista, with more than 150 upscale stores, including Neiman Marcus, Burberry, Gucci and Brooks Brothers.  Westchester's Ridge Hill  is a sophisticated outdoor shopping, dining and entertainment destination in Yonkers, and nearby, the  Cross County Shopping Center  offers favorites such as H&M, Macy's and Zara. Several other shopping destinations are located within the county, and its downtowns offer boutiques, art galleries and specialty shops. Even the rural countryside entices shoppers with antiques shops, artisan products and farmer's markets.

Outdoor Adventure and Splendor

Westchester County is graced with natural beauty. This backdrop is ideal for the active person looking for a place to  hike, bike and explore . Explore treasures like  Teatown Lake Reservation  and the Westchester County Farm Trail .

Helicopter Adventures over Westchester

Explore hidden gems and well-known landmarks from the air with Wings Air's scenic helicopter tours departing from Westchester County Airport. Helicopters seat two to six passengers and are available seven days a week, weather permitting. 30- and 45-minute tours are offered year round, all ages welcome. If you're feeling extra adventurous, you can try piloting your own helicopter under the supervision of a certified flight instructor. For more information, visit  wingsair.net  or call (914) 202-3440.

Water, Water Everywhere

Westchester is a paddler's paradise and boater's bliss, bordered by the Hudson River and Long Island Sound and bisected by large, scenic lakes.  George's Island  and  Croton Point  parks are just two of many places providing access to the Hudson, but some people prefer the ambiance of the pristine, 900-acre, three-mile-long Cross River Reservoir.

Along Long Island Sound, rent an umbrella and beach chair at  Playland's beach  or cool off in the pool. The city of New Rochelle is home to the county's second busiest park,  Glen Island Park , which boasts a beautiful crescent-shaped beach.

There’s always something going on in Westchester. For more great resources on things to do, visit ArtsWestchester , westchestergov.com and Westchester Magazine . 

North America Chevron

United States Chevron

New York Chevron

The Perfect Weekend in Westchester, New York

At first glance, Westchester doesn’t quite fit the bill for an exotic weekend away. Beautiful? Yes. Quaint? Absolutely. But Westchester as a travel destination? Yet with its convenient location—it starts a mere 12 miles from Manhattan —and 450 square miles of riverfront parks, trails, historic sites, and cultural attractions, it’s time to rethink New York’s famous county. According to the 2015 census, Westchester County is home to almost one million people living among its picture-perfect towns, Tudor homes and smaller urban environments—and for good reason. Not only is Westchester rich in natural landscapes, but with its robust road and transit connections, it’s an easy trip from New York City, Connecticut, and New England . It’s no wonder then that Manhattan’s most powerful families built their weekend castles in Westchester in the early 19th Century, and since then it has grown into one of the most luxurious and accessible suburban enclaves in New York, complete with top class restaurants (one James Beard award-winning spot included), numerous hiking trails, and grand old buildings to explore.

The Bedford Post Inn.

CHECKING IN:

In 2007 Westchester residents Richard Gere and Carey Lowell refurbished Bedford Post Inn , an eight-room inn dating back to the 1860s. Situated in the center of tony Bedford, it offers daily yoga and has two restaurants on site: The Barn offers casual lunch and breakfast, while Campagna is a high-end dining experience where a meat-heavy menu is sprinkled with local ingredients. Rooms are tranquil and geared towards relaxation, with neutral hues, canopy beds, and working fireplaces—we recommend booking a room with a terrace overlooking the wooded grounds. With its rustic-chic vibe, the inn lures a cosmopolitan crowd who desires an upstate-style getaway without having to travel far.

Meanwhile, 19 miles south in White Plains, Westchester’s urban hub, is the The Ritz-Carlton New York, Westchester , a full-scale resort with 38 suites, a state-of-the-art business center, indoor rooftop pool, decadent spa program, and Laurent Tourondel’s BLT Steak. It has all the familiar trappings of a Ritz-Carlton property and, given its central location, different areas of Westchester County can be accessed with ease by both car and rail.

DAY 1: GO BACK IN TIME

Spend the day on Westchester’s Southwestern edge and learn how the region’s most beloved characters once lived. Fuel up at Black Cat Café , where Irvington’s early risers feast on monstrous egg burritos, traditional French toast, and steel cut oatmeal all featuring organic, hormone-free, and non-GMO ingredients. Then make your way to Sunnyside , a charming river view house on 10 acres that was home to author Washington Irving, best known for short stories Rip Van Winkle and The Legend of Sleepy Hollow . The tour guides, who are dressed up in formal looks of the time, love to explain how Irving designed the grounds himself with an arrangement of garden paths, winding wisteria vines, and water vistas inspired by buildings in Scotland and Spain.

Next stop is Lyndhurst , also known as the Jay Gould estate, one of the country’s prized Gothic Revival homes. Designed in 1838 by Alexander Jackson Davis, the property is complemented by 67 acres of landscape and features a comprehensive collection of original decorative art works. Take a few selfies before stopping for a lunch at the Bridge View Tavern in Sleepy Hollow, and admire the views of the Hudson River and Tappan Zee Bridge over burgers, barbecue platters, and craft brews outside in the beer garden. Afterwards, walk off the meal among the cyclists and runners on the river’s promenade and head towards the Sleepy Hollow Lighthouse . Though not active, it still draws visitors for its towering stature, tours and ecological exhibits. Finish the day at hilltop residence Kykuit , a 40-room manse built by oil tycoon John D. Rockefeller that features works by Pablo Picasso, Henry Moore, and Alexander Calder. Make sure to check out the property’s cavernous Coach Barn, with its collection of classic cars and horse-drawn carriages.

Assuming you booked a reservation exactly 60 days ahead (the maximum allowed time, and spots fill up almost immediately), visit Blue Hill at Stone Barns for a lavish “on the farm” dinner prepared by James Beard-winning chef Dan Barber. If you arrive early enough, walk over to the Stone Barns Center for Food and Agriculture, where you can join a guided tour and visit the greenhouse, planting fields and livestock. But even if you don’t, be prepared for an eye-opening culinary experience—the tasting menu, which changes daily, is generally agreed to have pioneered the farm-to-table movement now found across the country.

The Katonah Museum of Art.

DAY 2: GET OUTDOORS

A country day begins with a country-style breakfast at The Barn at Bedford Post, where Bedford locals and hotel guests kick off the morning with gourmet egg sandwiches on brioche, Dutch pancakes with New York maple syrup, and house-made granola and yogurt. If you can move afterwards, head to Outhouse Orchards in North Salem for a quintessential farm experience. Since the late 1800’s the Outhouse family has farmed the land and created a destination for visitors to enjoy sweeping views of the region—plus, it’s the place to pick apples, take hayrides and pose on the pumpkin patch over donuts and cider. Don’t forget to pick up a homemade apple pie or pumpkin cheesecake before leaving. While the bulk of applepicking takes place in the fall, it makes for a scenic walk throughout the year.

Work off your morning snack at Mountain Lakes Park , Westchester’s northernmost county park with 1,082-acres of trails, lakes and spectacular views. Take your pick of activities, from hiking to ice skating to fishing or, if you’re feeling adventurous, the park’s challenging ropes course. You’ll earn your lunch at Purdy’s Farmer and the Fish , a community-oriented restaurant in an antique, country-house setting with superb seafood (take advantage of the raw bar) and vegetables plucked from the outside garden. Spend the afternoon walking the Katonah Museum of Art , a 10,000 square feet building that houses major exhibitions—currently on display is an extensive exhibit of Matisse drawings—and hosts traveling shows, lectures and workshops.

Finally, end your day with dinner at the Inn at Pound Ridge , Jean-Georges Vongerichten’s casual yet elegant restaurant offering down-to-earth food with ingredients sourced from Hudson Valley and New England farms. You can’t go wrong with fresh ricotta and cranberry compote on grilled sourdough before moving onto the parmesan-crusted organic chicken.

Dinner at the Inn at Pound Ridge

DAY 3: HIT THE SHOPS

It may not be Madison Avenue, but Westchester encompasses a premiere luxury shopping experience that can rival the best of Manhattan. Greet the morning over smoothies at The Westchester , the high end mega-mall in White Plains that houses stores from the high-end (Gucci, Michael Kors, Tiffany) and medium-end (J.Crew, Sephora, Tory Burch). Once you’ve canvassed every floor, head to low-key Sal’s Pizza in Mamaroneck for one of the restaurant’s much-adored Sicilian pies. Arrive early or join the daily line snaking the sidewalk, filled with tourists and locals craving near-perfect dough, milky cheese, and fresh tomato sauce.

If it’s warm enough, stroll over to Harbor Island Park , also known as the “jewel of Mamaroneck.” This 4.5-acre park overlooks one of the loveliest harbors in Long Island Sound and offers impressive vistas of the sailboats cruising by Gold Coast Connecticut homes. In September, the park stages the Harbor Island International Beer Festival , with 200 breweries, 20 food vendors, and live music and entertainment. But if more shopping awaits, pop into nearby Scarsdale and hit up independent boutiques selling everything from luxury women’s fashion to upscale puppy treats. Stop by Beginnings Boutique , which offers contemporary women's and men's clothing from brands like Diane von Furstenburg, Robert Rodriguez, J. Brand, and Alice & Olivia.

And at the end of the day, grab a drink at the Lazy Boy Saloon before devouring the famous wings at Candlelight Inn, an unassuming dive bar with a cult “in the know” following throughout the greater New York area.

Recommended

Concorde Hotel New York

Arlo Williamsburg

New York Travel Guide

By signing up you agree to our User Agreement (including the class action waiver and arbitration provisions ), our Privacy Policy & Cookie Statement and to receive marketing and account-related emails from Traveller. You can unsubscribe at any time. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

10 Best Things to Do in Westchester, NY

By: Author Jessica Lam

Posted on Published: August 25, 2023  - Last updated: October 2, 2023

Categories New York

Thank you to Westchester County Tourism & Film for sponsoring this post on the best things to do in Westchester, NY. As always, all opinions are my own.

Searching for the best things to see and do in Westchester, NY ?

Adam and I recently went on a romantic weekend getaway in Westchester County, and it was absolutely amazing.

Westchester County has so much to offer, from centuries-old landmarks and historic sites, to incredible dining experiences, to beautiful nature.

It’s also a great easy getaway from Toronto, whether you’re looking to drive or fly – it’s about an hour drive from New York City or 8 hour drive from Toronto.

Here are some of the best things to do in Westchester County, New York!

Be sure to also follow me on Instagram and TikTok – I share a lot more content on those platforms that don’t make it to the blog!

Plan your trip to New York

If you’re planning a trip to New York , you might find these posts helpful:

• Looking for more things to do in Westchester? Hit up the best restaurants or takeout spots in Westchester .
• Road tripping around Upstate NY? Check out my guides on Lake Placid , Ithaca , the 1000 Islands , or Chautauqua County .
• Visiting New York City? Check out my 24 hour NYC itinerary , weekend NYC itinerary , or the best winter activities in NYC .

Best things to do in Westchester County, NY

• Wander through Untermyer Gardens

The Untermyer Gardens is one of the most beautiful gardens we’ve ever seen, and you can find this gem in Westchester County.

This historic 43-acre public park and gardens was created over a century ago by Samuel and Minnie Untermyer, and it’s part of the couple’s former 150-acre estate.

Samuel Untermyer was one of the most prominent lawyers of his time, and he was the very first lawyer in America to earn a $1 million fee on a single case!

The Walled Garden was definitely our favourite part of the entire gardens, and even the entrance to it was absolutely stunning.

This enchanting garden oasis is the perfect place for a romantic stroll, with so many beautiful sights and scenic views within the gardens.

Walking through the gardens literally felt like walking through a real-life fairytale!

The classical architecture, lush florals and greenery, and reflecting pools make the Untermyer Gardens such a unique spot to visit.

Don’t forget to head up to the Temple of Love, where you’ll get gorgeous views overlooking the Hudson River.

The Untermyer Gardens are completely free to visit, but they do accept donations to aid in maintaining and restoring the gardens.

They also host a variety of fun ticketed events including concerts, sunset yoga, and art workshops!

If you’re interested in seeing more, I’ve got a TikTok video featuring the Untermyer Gardens .

LOCATION: 945 N Broadway, Yonkers, NY

• Go on a mansion tour at Lyndhurst Mansion

A mansion tour at Lyndhurst Mansion is an absolute must for any history buffs.

This 19th century estate is one of America’s finest Gothic Revival mansions, with its intricate stonework, lavishly-decorated rooms, and Tiffany stained glass windows.

It was so cool learning about the history behind this majestic property, which changed hands between three prominent New York families over the decades.

Moving companies weren’t a thing back then, so every piece of furniture and decor within the mansion was accumulated between the different families!

We found it so fascinating to get a peek into how the wealthy lived back in the day, or even how people in general used to live.

The mansion had no plumbing back then, so servants had to fill the bathtub by hand, and families shared the same bathwater!

Of course, as technology evolved, electricity, heating, and plumbing were eventually introduced into the home.

Lyndhurst Mansion Bowling Alley

You can also see the mansion’s bowling alley that was built in 1894, but sadly you won’t be able to throw any balls, as it’s just there for preservation purposes.

Inside the bowling alley is also a tribute to both Helen Gould and Madam C. J. Walker (whose former estate is next door), both incredible and inspiring women who did a lot for the community during their time.

There’s also a beautiful rose garden on the property, but we sadly didn’t have a chance to see it during our visit!

Also, a fun fact: if you’ve seen The Gilded Age (which you can watch on Crave ), they actually filmed some scenes at the Lyndhurst Mansion!

LOCATION: 635 S Broadway, Tarrytown, NY

More historic sites in Westchester County

If you love visiting historic sites, here are some other cool spots worth adding to your Westchester itinerary:

• Kykuit : former estate to four generations of the Rockefeller family, beginning with John D. Rockefeller, who was once the richest man in America
• Washington Irving’s Sunnyside : former home of Washington Irving, author of “The Legend of Sleepy Hollow”
• The Armour-Stiner Octagon House : the only known fully domed octagonal residence in the world

• Explore Croton Gorge Park

Croton Gorge Park is a stunning 97-acre park at the base of the New Croton Dam, and the dam actually supplies New York City with all of its drinking water!

It’s also the third largest hand-hewn structure in the world, behind the Pyramids of Giza and Great Wall of China.

The original dam was built in the mid-19th century and was the largest dam in the world at the time, and the new dam was built in the early 20th century.

The park is the perfect spot for a picnic, and they’ve got plenty of picnic tables and grassy areas for you to lay out picnic blankets.

You’ll even get to enjoy scenic views of the picturesque waterfall while enjoying your picnic!

Entrance to Croton Gorge Park is $10 per vehicle (or $5 for park pass holders) from May through Labor Day, and free during the rest of the year.

There’s also a free parking lot on Croton Dam Road, right off of Croton Gorge Park (the road), with a footpath that leads you along the top of the bridge.

The bridge is pedestrian-only, and it offers up stunning views from every corner.

We visited both the park and the top of the bridge, and the views all around were amazing!

Throughout the year, people even do fishing, sledding, and cross country skiing at the park.

LOCATION: 35 Yorktown Rd, Croton-On-Hudson, NY

• Visit the Village of Sleepy Hollow

Yes, I’m talking about that Village of Sleepy Hollow that we all grew up hearing about!

This real-life Halloweentown was the inspiration behind Washington Irving’s “The Legend of Sleepy Hollow”, and the author is actually buried in the Sleepy Hollow Cemetery.

It was really cool visiting some of the most iconic sites in Sleepy Hollow, including the Sleepy Hollow Cemetery, Old Dutch Church, Headless Horseman Bridge, and Headless Horseman Statue.

Other fun facts about Sleepy Hollow: all of the street signs are orange and black, and the local high school’s team mascot is the Headless Horseman!

Halloween season is definitely the best time to visit Sleepy Hollow, with really fun events like The Great Jack O’Lantern Blaze , where you get to see over 7,000 illuminated pumpkins.

• Stroll along the different waterfront areas

Westchester County is bordered by the Hudson River to the west and the Long Island Sound to the east, so you’ll find plenty of gorgeous waterfront areas.

We really enjoyed checking out all the different waterfronts and enjoying all of the views!

Strolling along the riverside esplanade at the Scenic Hudson RiverWalk Park at Tarrytown was really nice, and it was also located by the really cute historic Tarrytown train station.

While you’re here, stop into The Bakehouse of Tarrytown , an adorable old-fashioned bakery and café within the train station!

The Ossining waterfront has two really cool structures if you’re lookin’ for a good photo opp.

We saw quite a few people kayaking and SUP boarding along the Hudson River, which would be a really fun activity if you wanted to get out on the water!

If you’re looking for somewhere to dine, 3 Westerly is an amazing seafood restaurant located along the waterfront, and Bigfoot Creamery is a fantastic ice cream kiosk next-door.

The Yonkers waterfront has a really nice walking path with stunning views, and they even host live outdoor concerts during the summer months.

We also saw people SUP boarding along the river here!

Be sure to stop into Dolphin Restaurant for an incredible seafood cuisine and Lost Borough for unique ice cream flavours.

All of the waterfront areas were really nice to explore, and they’d be especially nice to walk along for a post-dinner sunset stroll.

There are a lot more waterfront areas around Westchester County, but these were just the ones we visited!

• Kayak or SUP board along the Hudson River or Long Island Sound

With the beautiful bodies of water surrounding Westchester County, you’ve gotta get out and do something fun on the water!

We definitely would’ve gone kayaking or SUP boarding if there was time on our schedule.

We saw people out on the water when we visited different waterfronts around Westchester, and it looked like a lot of fun!

There are a good number of sport rental shops that offer kayak, canoe, and SUP board rentals in Westchester.

P.S. If you’re in the mood for rollercoasters, you can also visit Playland Park located alongside the Long Island Sound!

• Go café hopping

Get caffeinated at one of Westchester’s many cute cafés and coffee shops.

We wanted to have as much time to explore Westchester as possible, so we had quick café breakfasts during our entire weekend trip.

We love hitting up cafés and trying unique coffee drinks and pastries, so we were happy to check these spots out!

Coffee Labs Roasters

Coffee Labs Roasters, an artsy little coffee shop in Tarrytown.

There were quite a few people typing away on laptops or having chats with friends on a Friday morning, and it was a really nice atmosphere.

You absolutely need to try the Miel Lavender (their version of a lavender latte), which is definitely one of the best coffee drinks I’ve ever had.

LOCATION: 7 Main St, Tarrytown, NY

Muddy Water Coffee & Cafe

Muddy Water Coffee & Cafe is another really great and friendly coffee shop in Tarrytown.

It’s a great spot for takeout in Westchester , and they’ve got plenty of food options, from soups to samosas!

Their empanadas are a must-try – I had the black bean and mushroom empanada, and it was amazing.

I was in the mood for a unique summery drink, and they made me a cold brew lemonade, which I don’t think was on the menu!

LOCATION: 52 Main St, Tarrytown, NY

Other cafés we would’ve loved to have tried were Bluestone Lane (their brunch looks fantastic) and Mimi’s Coffee House (they have build-your-own avocado toast!)

• Go on an ice cream tour

Adam and I are big ice cream fanatics, and we always love trying unique ice cream flavours.

You’ll find plenty of fantastic ice cream shops in Westchester offering everything from the classics to more funky creations.

Lost Borough Ice Cream

Lost Borough Ice Cream is a super cool spot in Yonkers with a really fun interior and plenty of fun flavours handcrafted in small batches.

The Lavender Honey + Walnuts flavour was to die for, and we also really enjoyed the Coconut Sorbet.

Aside from ice cream and sorbets, you’ll also find banana pudding and boba (or bubble tea, to my fellow Canadians!)

LOCATION: 1 Larkin Plz, Yonkers, NY

Bigfoot Creamery

Bigfoot Creamery is a super cute ice cream kiosk in Ossining that serves up their own handmade ice cream alongside guest flavours, and you can find them at Henry Gourdine Park.

We tried an amazing Birthday Bash ice cream from Perry’s, a New York-based ice cream chain that’s been around for over 100 years!

LOCATION: 1A Westerly Rd, Ossining, NY

Other spots we would’ve loved to try include Longford’s Ice Cream for their small-batch ice cream and Village Creamery for their unique homemade flavours!

• Dine at the incredible restaurants in Westchester

Westchester County is a foodie’s haven, with so many fantastic restaurants offering up all kinds of cuisines.

We tried several amazing restaurants during our visit to Westchester County, which I’ll share our experiences about below!

Creative wood-fired pizzas are what you’ll find at this rustic and graffiti-covered spot in Dobbs Ferry.

We adored the unique Everything 2.0 pizza, which featured everything spice, egg sauce, a spicy house-made sausage, mozzarella, and parmesan.

Adam also got the Griddle Burger, which was really good!

LOCATION: 14 Cedar St, Dobbs Ferry, NY

Dolphin Restaurant

Dolphin Restaurant is a lovely riverside restaurant in Yonkers serving up Mediterranean-inspired seafood cuisine.

We enjoyed the 8oz Angus Burger and Crispy Flounder, and the complimentary garlic bread was super good.

It was my first time trying flounder, and it was delicious and seasoned to perfection!

LOCATION: 1 Van Der Donck St, Yonkers, NY

This upscale waterfront restaurant in Ossining serves up elevated American fare in their nautical-inspired space.

We got the Crunchy Rice Cakes, Wagyu Steak Tartare, and Roasted Halibut, and everything was fantastic.

They’ve also got a really beautiful riverside patio if you’re in a patio mood!

LOCATION: 3 Westerly Rd, Ossining, NY

Goosefeather

Goosefeather serves up Cantonese fusion cuisine at their gorgeous restaurant at the Tarrytown House Estate on the Hudson , a beautiful historic hotel in Tarrytown.

Chef Dale Talde is behind the menu at Goosefeather, who’s been on cooking shows like Top Chef and Chopped !

Every dish we tried on the menu was impeccable, but my favourite was definitely the Spicy Salmon Tartare.

Goosefeather also has a fantastic brunch menu, but sadly we weren’t able to fit brunch here into our schedule.

The Kung Pao Chicken & Mochi Waffles really caught our eye on the brunch menu, but they do have a Mochi Waffle dessert on the dinner menu!

LOCATION: 49 E Sunnyside Ln, Tarrytown, NY

More note-worthy restaurants in Westchester County

Blue Hill at Stone Barns is a two Michelin Star farm-to-table restaurant in Tarrytown, and reservations are very exclusive.

They also offer a more casual cafeteria experience during lunch hours.

There are over a dozen Bib Gourmand restaurants in Westchester as well, including:

• Dubrovnik for upscale Croatian delicacies
• RaaSa for modern Indian cuisine
• Shiraz Kitchen for Mediterranean sharing plates

A brunch spot we really wanted to try during our visit was Mt. Kisco Diner , but sadly it didn’t fit into our schedule.

They serve up an epic selection of pancakes and all-day breakfast, including their Cookie Monster Pancakes (which are blue!) and Cannoli Pancakes.

There are a lot of incredible restaurants in Westchester County , and we can’t wait to come back and try more spots!

• Stay at the historic Tarrytown House Estate on the Hudson

We stayed at the gorgeous Tarrytown House, a historic estate dating back to the early 1800s, during our stay in Westchester County.

The 26-acre property is absolutely stunning, and we loved that they blended the historical architecture with modern structures.

We enjoyed evening strolls around the property during both nights we stayed here, and it was so lovely.

We loved how serene our stay at the Tarrytown House Estate was, and it was only less than a 10 minute drive to get into the main downtown area of Tarrytown!

They’ve got one of the most incredible gyms I’ve ever seen in a hotel , and they’ve also got a basketball court, tennis court, and indoor and outdoor swimming pools.

We loved staying in Tarrytown and being so close to so many incredible restaurants and cafés.

The hotel is also only a few minutes’ drive away from Lyndhurst Mansion and Washington Irving’s Sunnyside!

If you’re looking for somewhere to stay during your stay in Westchester County, the Tarrytown House Estate on the Hudson would be a fantastic option.

🏨 Book a stay at the Tarrytown House Estate on the Hudson on Expedia

🏨 Book a stay at the Tarrytown House Estate on the Hudson on Booking.com

Best things to do in Westchester County:

These were some of the best things to do during your visit to Westchester County, New York!

If you want a breakdown of our full weekend itinerary, here it is:

We flew from Billy Bishop Toronto City Airport (YTZ) in Toronto to Newark Liberty International Airport (EWR) in New Jersey, which was only about an hour flight.

We then grabbed our car rental and drove about an hour from Newark over to Yonkers.

• Lunch at Dolphin Restaurant
• Dessert at Lost Borough Ice Cream
• Explore Untermyer Gardens
• Dinner at Goosefeather

This was our only full day in Westchester County, so we wanted to make the most of it!

• Breakfast at Coffee Labs Roasters
• Lunch at 3 Westerly
• Dessert at Bigfoot Creamery
• Dessert at The Bakehouse of Tarrytown
• Explore Lyndhurst Mansion
• Dinner at The Parlor
• Explore Sleepy Hollow

We had a quick last breakfast in Westchester before returning our car rental at the airport.

• Breakfast at Muddy Water Coffee

Westchester is such a fantastic and easy getaway from Toronto and there’s so much to see and do, whether you’re a history buff, foodie, or nature lover.

Have you been to Westchester County before? What are your favourite things to do in this beautiful part of New York State? Let me know on Twitter or Instagram !

Be sure to keep up with me on  Instagram , TikTok ,  Twitter , Facebook , and  Pinterest  if you aren’t already!

Feel free to subscribe to my weekly newsletter to get my blog posts delivered straight to your inbox.

Like this post? Pin it for later!

Sharing is Caring

Help spread the word. You're awesome for doing it!

10 Best Towns Westchester County

Hash-mark 10 best towns in westchester county (2024).

• New Rochelle
• Dobbs Ferry
• Briarcliff Manor

hash-mark 1. Rye

Rye is the best place to live in Westchester thanks to its wonderful character, stellar safety record, and proximity to NYC.  Rye is a small town on the coast near the Connecticut border that offers the quaint charm of a New England town with gorgeous architecture and a walkable downtown area. Plus, it’s less than an hour into Grand Central on Metro-North.

Rye offers all the benefits of a small town with easy access to urban amenities. It has excellent public schools, low crime, and plenty of golf courses, restaurants, and community centers. Plus, the city features over 454 acres of public green space that is open to everything from hiking to birdwatching. Rye has something to offer everyone with a good blend of serenity and excitement.

hash-mark 2. New Rochelle

Another one of the best towns in Westchester is New Rochelle. This town is located at the southern end of Westchester County, right outside New York City. It offers a nice blend of suburban atmosphere and urban excitement. Its downtown area is on the rise and features a burgeoning art scene, as well as an impressive selection of bars, restaurants, and shopping.

It also offers award-winning public schools and one of the lowest crime rates in New York. Plus, it’s only a 30-minute train ride into New York City, making it perfect for commuters. New Rochelle is ideal for those who enjoy the energy of a major city without all the hassles of living directly in Manhattan. 

hash-mark 3. Bronxville

Another one of the best places to live in Westchester is Bronxville. This small village in southern Westchester County is located about 15 miles outside of Midtown Manhattan. It’s a small yet highly desirable area with some of the most expensive real estate in New York. It offers a quaint, small-town charm with an easy commute into Manhattan.

Bronxville High School is ranked among the best in the country and is well known for its competitive sports and academic programs. Plus, it features a bustling downtown area with plenty of great mom-and-pop shops, bookstores, and local restaurants. Bronxville features a picturesque atmosphere that looks like something out of a movie. But it’s also very expensive, and the average home in the village is over $1.4 million.

hash-mark 4. Dobbs Ferry

Dobb’s Ferry is also one of the best towns to live in Westchester County, as it offers beautiful nature in a tranquil setting and an easy commute to NYC. It’s a peaceful area with gorgeous tree-lined blocks and friendly neighbors. In 2014, it became the first city in New York State to be designated a Climate Smart Community for its dedication to sustainability.

It’s known to be a family-friendly village with excellent public schools and plenty of parks and community centers readily accessible. Waterfront Park, for instance, is located along the banks of the Hudson River and features playgrounds, sports fields, and plenty of open green space. Mercy College is also located in Dobbs Ferry, offering educational and employment opportunities. Dobb’s Ferry is ideal for those who want a safe place to raise a family with an easy commute into Manhattan.

hash-mark 5. Irvington

Irvington is another one of the best places to live in Westchester County. This small suburban village is located within the city of Greenburg, right next to Dobb’s Ferry along the Hudson. The village is known for its affluent residents and was ranked by Bloomberg as 54th on a list of America’s wealthiest places. Irvington features a half-mile-long main street area full of unique shops and restaurants.

Irvington has a relaxed atmosphere and friendly community with convenient access to Manhattan, only 40 minutes by car or Metro-North. It also features a variety of local attractions, such as the Irvington Theater, which regularly hosts live plays and films. Irvington is a lively yet laid-back village with charming energy that many residents love.

hash-mark 6. Edgemont

Edgemont, also known as Greenville, is   another popular village within the city of Greenburg that is one of Westchester’s most coveted areas. Originally designed as a summer destination for wealthy Manhattan residents, Edgemont features some gorgeous homes in the antique colonial style. The village is also known for its great public schools, which US News and World Report ranked as the 14th best in the state and 87th best in the country. Edgemont is also a city for the affluent and was ranked number 22 on Bloomberg’s list of wealthiest places in America. But if you have the budget, the village offers fantastic schools, high quality of life, and easy access to Manhattan. 

hash-mark 7. Chappaqua

Chappaqua is a hamlet in the town of New Castle, located in northern Westchester County. Located less than an hour outside of Manhattan, Chappaqua is a popular bedroom community with a Metro-North station that stops at Grand Central. The village has been home to various famous residents, including Bill and Hillary Clinton, hedge fund manager Bill Ackman and actor Ben Stiller. It’s a small yet inviting town with plenty of parks, great schools, and a low crime rate. While Chappaqua is still fairly expensive compared to the national average, housing prices aren’t quite as high as some of the towns located directly outside Manhattan. 

hash-mark 8. Briarcliff Manor 

Briarcliff Manor is also one of the best towns Westchester County. It is located about 30 miles north of New York. It’s been nicknamed the village between two rivers for its position in between the Hudson and the Pocantico Rivers, and it offers a nice blend of nature and convenience.

The town was known as the home of wealthy New York families like the Rockefellers, the Astors, and the Vanderbilts, and there are several historic mansions in the village. Briarcliff Manor also has about 180 acres of public recreational facilities and parks, which are maintained by the Village’s Department of Public Works. Briarcliff Manor is still considered an affluent suburb, but for those with the budget, it’s a great place to raise a family and still commute to New York. 

hash-mark 9. Scarsdale

Scarsdale is a peaceful village in Southern Westchester County. It’s known for its welcoming community, which hosts frequent volunteer programs and public events. Just 35 minutes from Manhattan, it’s a town full of commuters but offers the peaceful atmosphere of a suburb with tree-lined streets and open green space. Plus, it has a brand-new public library, well-regarded schools, and a Metro-North station that leads right into Manhattan. Scarsdale is also considered very affluent and was ranked by Bloomberg as one of the richest towns in the United States.

It’s easy to see why Scarsdale is considered one of the best towns in Westchester County, as it offers residents a high quality of life and easy access to urban amenities. 

hash-mark 10. Tarrytown

Tarrytown is a village in the city of Greenburg located north of Irvington and Dobbs Ferry along the Hudson River. The village features a quaint main street with a great selection of local restaurants and boutiques. The Tarrytown Music Hall is at the heart of the downtown area and hosts performances by famous musicians and comedians.

The Hudson River Walk is another local attraction that features an esplanade along the water with green space filled with native plants. With a laidback atmosphere and direct access to Grand Central, Tarrytown is another popular destination for commuters in search of a quiet place to raise a family. 

Share this article

• Route planner

Westchester County

The best walks and hikes in Westchester County

Want to go hiking in Westchester County to explore more of this corner of New York? In this guide, we’ve reviewed our full collection of hikes and walking routes in Westchester County to bring you the best hiking routes in the region. To see which of our walks in Westchester County is the right one for you, browse real tips and photos uploaded by other hikers—and see what they had to say about each walk.

Plan. Save. Navigate. Your best adventures await.

Start today with a free komoot account.

Old Croton Aqueduct via Upper Trail loop — Rockefeller State Park Reserve

Turkey mountain trail loop — turkey mountain park.

Let us show you the way with the komoot mobile app

Anthony's nose via camp smith trail — bear mountain state park, sleepy hollow to swan lake via barnyard hill — rockefeller state park reserve, yellow & hawk watch trail loop — butler sanctuary, red & blue trail loop — mianus river george preservation, buttermilk hill via old orchard trail — rockefeller state park reserve, swan lake loop – rockefeller state park preserve, raven rock overlook loop — ward pound ridge reservation, teatown lake reservation loop — westchester county.

Our Tour recommendations are based on thousands of activities completed by other people on komoot.

Popular around Westchester County

Find the perfect Tour

Explore the most popular tours in westchester county.

Easy hikes in Westchester County

Road Cycling Routes in Westchester County

Cycling in Westchester County

MTB Trails in Westchester County

Running Trails in Westchester County

Waterfall hikes in Westchester County

Gravel biking in Westchester County

Discover the most popular attractions in Westchester County

Attractions in Westchester County

Lakes in Westchester County

Didn’t find what you were looking for? Check out more Hikes throughout Westchester County below and find the perfect Tour in your destination.

• Sleepy Hollow
• Mount Vernon
• Port Chester
• Lake Mohegan
• Jefferson Valley-Yorktown
• White Plains
• Franklin Delano Roosevelt State Park
• Hastings-On-Hudson
• Salt Hill State Forest
• Briarcliff Manor
• Golden'S Bridge
• Rockefeller State Park Preserve
• Yorktown Heights
• Pelham Manor
• Eastchester
• Scotts Corners
• Croton-On-Hudson
• Dobbs Ferry
• Donald J. Trump State Park (French Hill Unit) (Closed)
• Montrose Point State Forest
• Mount Kisco
• New Rochelle
• Pleasantville
• Bedford Hills

Explore more of New York : Browse the best Hikes in other regions.

• Essex County
• New York County
• Ulster County
• Rockland County
• Orange County
• Greene County
• Tompkins County
• Hamilton County
• Suffolk County
• Putnam County
• Warren County
• Washington County
• Schuyler County
• Erie County
• Herkimer County
• Columbia County
• Onondaga County
• Ontario County
• Bronx County
• Saratoga County
• Oneida County
• Clinton County
• Albany County
• Kings County
• Monroe County
• Dutchess County
• Niagara County
• Yates County
• Seneca County
• Richmond County
• Sullivan County
• Lewis County
• Delaware County
• Franklin County
• Cattaraugus County
• Cayuga County
• Chautauqua County
• Schenectady County
• Fulton County
• Wayne County
• Chemung County
• Broome County
• Rensselaer County
• Nassau County
• Steuben County
• Livingston County
• Queens County
• Cortland County
• Madison County
• Wyoming County
• Allegany County
• St. Lawrence County

7 Charming Historic Towns In NY To Visit Right Now

For when you're looking for a quick getaway–especially with the approaching fall season–plan a trip to one of these gorgeous historic towns in New York.

We’re not saying we don’t love living in New York City, but sometimes we just need a change of scenery, and from small towns to charming beach towns to these underrated towns there are so many places to explore.

And with fall travel on our mind we’re lucky enough that New York is filled with stunning historic towns to explore that offer breathtaking scenery–think: sprawling mountains , glistening blue lakes , and rolling hills–and they all make for quite the perfect quick escape or day trip from NYC!

World Atlas highlighted seven of New York’s most beautiful and well-preserved historic towns that should be on everyone’s New York travel itinerary.

From towns that saw action during the Revolutionary War to the town that was the birthplace of baseball, these towns add to the state’s charm, showcase America’s history, and draw visitors from all over. Here are seven historic towns in NY to visit, as according to World Atlas:

1. Cooperstown

Nestled near Otsego Lake in central New York, Cooperstown is a small village surrounded by hills founded in 1786 by William Cooper (the father of renowned American novelist James Fenimore Cooper).

Most known as being the home to the famous National Baseball Hall of Fame and Museum, upwards of 300,000 visitors walk the streets of Cooperstown each year to admire its waterfront views, 19th-century architecture, and Revolutionary War history.

🚗 ~3.5 hours

2. Skaneateles

We’ve suggested a trip to the Central New York town Skaneateles many times–it’s one of the most underrated towns in NY to take a trip to, one of the most picturesque small towns in NY, and a perfect Labor Day getaway. But the town is mostly known for its beautiful lake (formed by glaciers millions of years ago) and diverse architecture.

Skaneateles is enveloped by gentle hills, is home to a charming downtown marked by tree-lined streets, and is filled with beautifully diverse architectural styles. The town has a rich history and its historical landmarks include the John D. Barrow Art Gallery and The Sherwood Inn which was founded in 1807.

Situated on the eastern side of Cayuga Lake in Central New York as part of the Finger Lakes region, Aurora features stunning water views, picturesque rolling hills, and a downtown filled with historic buildings and many well-preserved attractions.

The town was once home to six Native nations though revitalization efforts supported by Pleasant Rowland, creator of the American Girl brand, has since added a new charm to the town.

4. Cold Spring

Cold Spring was founded in 1730 by Thomas Davenport and got its start as a small trading post along the Hudson River before becoming a major industrial hub during the Civil War. The town was officially incorporated in the mid-1800s.

Today, Cold Spring showcases many well-maintained 19th-century buildings and, being its surrounded by the Hudson highlands, features stunning river views.

🚗 ~1.5 hours

5. Seneca Falls

Located in the Finger Lakes district on the Seneca River, Seneca Falls, which was first settled in 1787, is a historic hub for women’s rights due to it hosting the 1848 Seneca Falls Convention. Today, the village is the site of the National Women’s Hall of Fame.

Beyond its history, Seneca Falls is known for its charming downtown with water views and Victorian architecture. It’s also believed to have inspired the fictional Bedford Falls in Frank Capra’s It’s a Wonderful Life !

6. Sackets Harbor

Founded in 1801, Sackets Harbor played a key role in the War of 1812, serving as the headquarters for the army, navy, and marines. The village’s Madison Barracks provided housing for soldiers during the war and later became a ship building center in World War II.

As the village sits on the eastern edges of Lake Ontario, Sackets Harbor features picturesque waterfront views and its downtown is filled with stunning 19th-century architecture such as the Sackets Harbor Battlefield State Historic Site.

7. Ballston Spa

Ballston Spa was established two years before the Revolutionary War and has since become a popular destination for visitors from all over due to its natural spring.

Beyond the spring, however, the village is also home to Victorian-style homes, historic landmarks, and attractions such as the National Bottle Museum and Saratoga County Historical Society, which make it a must-visit.

TYPE IN YOUR SEARCH AND PRESS ENTER

10 Unique & Fun New York Towns You Didn’t Know You Needed To Visit

*FYI - this post may contain affiliate links, which means we earn a commission at no extra cost to you if you purchase from them. Also, as an Amazon Associate I earn from qualifying purchases. Check out our Privacy Policy and Disclosure. for more info.

The following list of New York towns to visit is brought to you by New Yorker, Aurie Ceylon from  hey, it’s aurie ! Read on for some of her top recommendations !

Completely biased opinion: New York State is the best . 

I love exploring New York, and I always say that I will probably (definitely) never live anywhere else, because why would I? From small towns to bustling cities, beaches to mountains, lakes to rivers, and – oh yeah – Niagara Falls! – we truly have it all. 

There are tons of exciting nooks and crannies of New York State to explore, spanning from Long Island to Upstate and beyond… but where can you find the most exciting hidden gems of New York? The obscure, sleepy, and sometimes forgotten small towns!

Rich with history, scenery, architecture, and food, these towns, villages, and hamlets give the Empire State its charm.

Unsure where to begin? Don’t worry, I’ve got your back. Stick with me as we explore a list of unique and fun New York towns you seriously did not know you needed to visit!

Save this List of New York Towns for Later!

You’ll be very glad you did.

Prepare for some of the most breathtakingly charming views of your entire life (says the wildly unbiased New Yorker who just went to Beacon for the first time ever!) .

Without a doubt, Beacon is one of the most idyllic and picturesque towns in New York State. Located on the eastern shore of the Hudson River, Beacon is a small but mighty upstate riverside town that is well worth the trip. Just a 90-minute drive from the hustle and bustle of New York City, Beacon feels like you’ve wandered light years away to a quaint, rustically stunning town that rivals every Hallmark movie you’ve ever seen.

What to do in Beacon: Stroll the winding and seemingly endless Main Street, where you’ll find yourself over-saturated with vintage shops, cafes, record stores, boutiques, and a surprising array of multicultural cuisine. Follow the street through the town (make sure to stop at El Nica in the Hudson Valley Food Hall for the best Nicaraguan steak of your life) until you reach Fishkill River. There, you can marvel at South Beacon Mountain, an overwhelming mass that seems to swallow the town whole. 

Bonus : If you’re there on a Sunday, you must stop by the Beacon Farmers Market !

A perfect day for the rustic wanderer. 

2. Port Jefferson

I can’t gush enough about this adorable maritime town. Located on the north shore of Long Island and originally incorporated in the mid-17th century, this historic waterfront village is nothing short of a tourism hot spot and real estate gem. With stunning ‘painted lady’ Victorians, quaint coffee shops and bookstores, and even the ruins of a cliffside PINK MANSION (rumored to be the former home to a European duchess!), Port Jefferson is full of places to explore. Its stunning location on the Long Island Sound guarantees breathtaking waterfront views, year round. 

What to do in Port Jeff: Spend the day exploring the shops on Main Street (or up and down the residential roads, marveling at historic homes). Grab dinner at PJ Lobster House , one of Port Jefferson’s top-rated places for informal-yet-mouthwatering seafood. (This Long Islander has been dining at the Lobster House since I was a kid, and it never disappoints!) End your night with homemade ice cream and fudge from Port Jefferson Ice Cream Cafe and sunset at the marina. 

Want to stay in Port Jeff overnight? Book a room at Danfords Hotel & Marina , located on the water in the heart of Port Jefferson. Along with an on-site spa, wellness center, and top-rated restaurant, guests can also park their boats in the marina! It doesn’t get more maritime than that.

An idyllic town for the nautical wanderer !

3. New Paltz

Tucked away in the mountainous woods of Ulster County, New Paltz is the quiet college town you’ve been looking for.

With multicolored shops and restaurants lining the main street and Paltz Point views bordering the town, it feels like you’ve basically stepped onto the set of Gilmore Girls .

On top of being a dream for woodsy adventurers, New Paltz is also home to SUNY New Paltz, one of the top liberal arts colleges in the Hudson Valley region. Only a 90-minute drive from New York City, New Paltz has the rustic and historic feeling of a world very far away from the chaos of city life.

What to do in New Paltz: Grab breakfast at Main Street Bistro or B Side Grill , which will undoubtedly be chock full of locals, students, and families (especially on weekends!). Walk along Main Street, exploring the dozens of used bookstores and novelty shops, OR head to Mohonk Preserve and take in over 8,000 acres of forests, fields, and streams. 

Perfect for the woodsy wanderer .

4. Greenport

As a Long Islander who had never been to Greenport, I didn’t know what to think about this mysterious north shore town, especially on a trip during one of the coldest weeks of the year.

But, I’m here to say: Greenport is incredible , even off-season.

Bordered by the Long Island Sound, Greenport Harbor, and Pipes Cove, Greenport is a tiny, picturesque waterfront town that takes a good long snooze in the colder months.

But, while seasonal shops and restaurants close up for the winter, the hamlet thrives on community and local tourism. With only 2,100 residents, winter in Greenport feels like you have the entire incorporated village to yourself! But, not to fear, friends. From wineries to local diners, there is something for every winter wanderer…even those who can’t stand the cold!

Fun Fact: For the history buffs (and perhaps, paranormal buffs?), check out The Old Greenport Jail. Built in 1917, the terribly tiny-and-spooky jailhouse was in use until the Greenport police department was disbanded in 1947, after a history of scandals! Walk by after dark, if you dare!

What to do in Greenport: Start your day with breakfast at the charmingly vintage Crazy Beans (the gluten free pancakes are amazing! ), then stop by The Old Greenport Jail for a dose of passerby history. Stroll to the water, then hop on the ferry to Shelter Island, an even quieter and more mystifying seasonal hamlet. Dine on Shelter Island or – for wine lovers – head back to the mainland and check out Kontokosta Winery for breathtaking cliffside views and the best Chardonnay of your life (not kidding). Grab dinner and listen to live music at First & South (get the Mac & cheese!).

After that, grab your bottle of Kontokosta wine and head home! That’s the thing about seasonal towns…they close early!

Ideal for the tiny townie coastal wanderer !

5. Bearsville

Hiking, abandoned hotels, Buddhist monasteries… Am I describing the next big Coen Brothers movie? No, friends. Welcome to Bearsville.

Located in Ulster County, Bearsville is the high altitude meditative escape you didn’t know you had to see. With a population of only 700 and a very wooded atmosphere, it’s easy to miss this tiny hamlet! But, for the wanderers looking for an overlooked adventure, this is the place for you. Take the only slightly terrifying drive up Overlook Mountain, where you will catch glimpses of the breathtaking (and jaw-dropping) views that await you at the very top! 

Fun Fact: For those looking for a bit of ominous history, check out the Overlook Mountain House ! Originally built in 1841, Overlook Mountain House was destroyed by not one but TWO fires, one in 1875 and again in 1923! The house was used as a hotel, and even as a meeting place for a top-secret society in the 1920s. It is now part of the Catskill Forest Preserve and sits, undisturbed and publicly accessible, on the Overlook Mountain trail. 

What to do in Bearsville: Hike the extremely steep and rocky trek up Overlook Mountain, stopping along the way to check out the abandoned and ever-spooky Overlook Mountain House! When you reach the summit of Overlook Mountain – for the daredevils – climb the very shaky observation tower for panoramic views of the Catskill Mountains. Once you’ve descended Overlook, stop by the Karma Triyana Dharmachakra Monastery for some much needed (publicly accessible) peace and quiet. 

A perfect destination for the adventurous (and meditative!) wanderer .

6. Kingston

Cobblestone streets, historic colonials, a bookstore winery. Are you sold yet? Welcome to Kingston, New York’s original state capital. From stunning stone-clad architecture to a vibrant downtown center, Kingston is a breath of historically fresh air. 

Fun Fact: Kingston is the only city in Ulster County. It is also the Empire State’s original state capital. But did you know that Kingston was once burned to the ground? During the American Revolutionary War, the city was burned down by the British in 1777 as punishment for aiding Patriots. The city was later rebuilt and flourished in the 19th century for its natural cement, as well as its railroad and canal connections to other hubs around New York State. Today, Kingston is known for its stunning riverfront and mountain views, as well as its incendiary colonial history.

What to do in Kingston: Stroll the stone sidewalks and cobblestone streets, taking in stunning views of 18th century homes, then shop at Kingston’s Uptown Farmers Market and lose your mind buying raw honey and soft cheese (why do soft cheeses always taste better upstate?). When you’ve sufficiently shopped til you’ve dropped , head to dinner at Front Street Tavern or pop across the street to the oh-so-charmingly-historic Hoffman House Tavern , located in a preserved 1679 stone house! Before you call it a night, stop by Rough Draft Bar & Books for – you guessed it – a glass of wine and a quick read.

A great escape for the historical wanderer .

7. Woodstock

Calling all quirky artsy folk ! This is the town for you. Located in Ulster County, Woodstock is a bohemian dream.

With a historic town center and the Catskills bordering the town’s edges, it’s easy to imagine meandering through the foliage and marveling at the quaint shops and cafes all day long. A mecca for artists, musicians, and general ‘quirky’ travelers, Woodstock feels like the warm, vibrant, charming, and colorful town you’ve been looking for. 

What to do in Woodstock: Aside from the ever-glorified annual Woodstock Film Festival , take in the charm of boutiques and shops on Tinker Street! Grab the best noodle bowl of your life at Yum Yum Noodle Bar (I’m serious!), and indulge on fudge, truffles, and Woodstock merchandise at one of the many oddball shops.

If you don’t leave with at least one oversized tie-dye shirt and a box of fudge, you did it wrong.

Feeling musical? Take a Rock’N’Roll History Tour , where you’ll stroll the streets and hear stories about Bob Dylan, Janis Joplin, and more!

A must-see for the hippie-dippie wanderer .

Montauk is the complete opposite of everything glitz and glam. Located on the south shore of Long Island and bordered by the Atlantic Ocean and Block Island Sound, this seaside village is just about as authentic as Long Island gets. For tourists and wanderers looking to avoid the oh-so-trendy neighboring beaches of The Hamptons, you can’t skip this Lobster-encrusted jewel. Yes, lobster .   

Fun Fact: Montauk is the easternmost point in New York State! It has been nicknamed “the end of the world” for its vast and seemingly endless views of the ominous Atlantic Ocean. 

What to do in Montauk: Check out Montauk Point State Park , home to New York State’s first lighthouse, a well preserved relic now protected by the Montauk Historical Society. Commissioned by President George Washington in 1792, Montauk Point Lighthouse is the fourth-oldest active lighthouse in the United States! Located at the easternmost tip of New York, visitors can climb the 137 iron steps to the top, where you can take in 360 degree breathtaking views of Long Island, the Atlantic Ocean, and beyond.

Want to explore “the end of the world” overnight? Book a room at Montauk Manor , Montauk’s national landmark hotel!

This is a must-see for the adventurous (and heights-thrilled!) wanderer .

9. Shelter Island

Remember the tiny waterfront town of Greenport? Well, I’ll let you in on a secret: If you hop on the ferry (all you need is a $3 token!) and cruise 5 minutes across the Shelter Island Sound, you will find yourself on a 12-mile seasonal island, populated by quiet tourists and overflowing with nautical and historic homes.

With a population of over 3,000 Long Islanders, it sounds like Shelter Island should be a bustling town. But, trust me – Shelter Island (especially in the winter months) is as sleepy as sleepy gets. With most of the popular restaurants and breweries shuttered and dark during the off-season, I would definitely recommend saving this trip for the warmer months. 

What to do in Shelter Island: When you’ve finished marveling at the original shutters and wooden shingles of the 18th century homes, stop for lunch at the oh-so-authentic Commander Cody’s Fish Shoppe . This ‘no frills’ local gem is chock full of Long Island favorites. From fried oysters to pulled pork, you’ll leave stuffed and happy. For a cute throwback, pop into Shelter Island Heights Pharmacy , where you can sit at the 1950s-style counter and slurp down strawberry milkshakes and cheese fries. If you’ve still got room for more, stop by Sunset Beach for breathtaking waterfront views and fancy French fare. 

Looking to explore the island overnight? Book a room at Shelter Island House – a top rated B&B-style hotel, located a few steps from Crescent Beach!

This spot is a must for the sleepy upscale townie wanderer .

BONUS: Astoria

Okay, I know what you’re thinking: This is the part where the New York City-based writer talks about how amazing her neighborhood is, right? Absolutely! Let’s talk about Astoria. 

Astoria is located in Queens (one of the five boroughs of New York City) on the East River. A stone’s throw away from Randall’s Island, The Bronx, and Manhattan’s Upper East Side, Astoria is a commuter’s dream come true. It also has breathtaking views, incredible food, and outrageous real estate. Astoria is bordered by 4 other Queens neighborhoods: Long Island City, Woodside, Sunnyside, and Elmhurst. What does this mean? A culturally, religiously, and ethnically diverse metropolis with never-ending things to do, places to go, and food to eat (huzzah!). 

What to do in Astoria: Where do I begin? Bar and brunch hop on Ditmars Boulevard or 30th Avenue, check out the oldest beer garden in New York City at Bohemian Hall & Beer Garden , take in outdoor art installations at Socrates Sculpture Park , dine on incredible Greek food at Gregory’s Corner Taverna or Amylos Taverna (get the lemon potatoes, trust me ), then take in the NYC skyline at sunset from the ever-idyllic Astoria Park. 

*Bonus* – There’s even a carnival in the summer!

Astoria is a must for the city-loving wanderer .

Did I miss any of your favorite towns in New York?

Let me know in the comments so I can add more recommendations to the New York list!

My Go-To Travel Favourites:

🧳 Eagle Creek: My favourite packing cubes

💳 Wise: For FREE travel friendly credit cards

🍯 Airalo: My go-to eSIM

🏨 Booking.com: For searching hotels

📷 Sony A7IV: My (amazing) camera

✈️ Google Flights : For finding flight deals

🌎 WorldNomads: For travel insurance

🎉 GetYourGuide: For booking activities

Leave a Comment Cancel reply

By using this form you agree with the storage and handling of your data by this website. *