places to visit in berkshire for couples

THE 10 BEST Couples' Activities & Things to Do in Berkshire

Best things to do in berkshire for couples.

• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• Good for Couples
• Budget-friendly
• Good for Big Groups
• Good for Kids
• Good for a Rainy Day
• Hidden Gems
• Good for Adrenaline Seekers
• Adventurous
• Honeymoon spot
• Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

1. Windsor Castle

2. St. George's Chapel

3. Windsor Great Park

4. Basildon Park

5. Theatre Royal Windsor

6. Windsor & Eton Brewery

7. Stanlake Park Wine Estate

8. Ascot Racecourse

9. The Watermill Theatre

10. Black Park

11. Boulter's Lock and Ray Mill Island

12. Dinton Pastures Country Park

13. Tally Ho Stables

14. Dorney Court

15. Forbury Gardens

16. Welford Park

17. Langley Country Park

18. Kennet & Avon Canal

19. Nature Discovery Centre

20. Royal Ascot

21. Donnington Castle

22. Caversham Court Gardens

23. The Long Walk

24. Hungerford Wharf

25. Feathers and Fur Falconry Centre

26. Combe Gibbet

27. Harris Garden

28. Escape Reading

29. Genting Casino Reading

30. TimeTrap Escape Rooms

What travellers are saying

Attractions in the Berkshires for Romantic Couples

Massachusetts' Berkshires are an Ideal Destination for Fun-Loving Couples

The sylvan Berkshire Mountains have for centuries lured artists and writers, millionaires and scoundrels (these were often one and the same), and romantic couples just like you in search of fun, entertainment, and a bit of culture. Graced with natural beauty, the Berkshires also boast some of the loveliest cultivated scenery in America. When a romantic couple decides to spend time here, that becomes a backdrop for days of fun and exploration. What's not to be missed? These are some top attractions in the Berkshires for a couple in love to explore.

The Mount: A National Historic Landmark

Vincent Sardone

Opened in 1902, The Mount became author Edith Wharton's haven. The Gilded Age mansion was designed in accordance with the principles she espoused in The Decoration of Houses ; many consider this a seminal book in the field of interior design. Not only did Wharton create a house and garden of proportion, harmony, and symmetry, she also authored some 40 books in 40 years, including The Age of Innocence and The House of Mirth .

A restoration work in progress, The Mount (entrance fee) hosts cultural events (check the website for the schedule). Have a drink and listen to live jazz summer weekend evenings on the terrace overlooking the formal gardens. The Mount is open May through October and on weekends in November and December. 2704, 2 Plunkett St, Lenox.

Hancock Shaker Village: A National Historic Landmark

It might not seem like a couple's first choice of a place to visit for fun in the Berkshires — after all, the Shakers were a religious sect dedicated to simplicity, community, and celibacy . Their heyday extended from 1783 to 1960. Given their lack of fecundity, it's unsurprising that none are left.

Yet their good works live on, proving that you can get a lot done when your mind is on other things. At Pittsfield's 1,200-acre Hancock Shaker Village (entrance fee), learn about the group and how they lived via a short video. Adjacent galleries display the distinctive chairs, tools, and boxes their busy hands fashioned. Then stroll the grounds to see the round barn, historic buildings, and garden that are the enduring fruits of their labor. 1843 W Housatonic St, Pittsfield.

Norman Rockwell Museum

Known as the man who illustrated covers of The Saturday Evening Post with visions of a wholesome and optimistic Americana, Norman Rockwell lived and painted in Stockbridge. This museum (entrance fee) dedicated to Rockwell was designed by architect Robert A.M. Stern and features a 15-minute biographical video that describes his life, his work, and his values. The museum's collection consists of more than 600 of Rockwell's patriotic paintings as well as his many magazine covers. Visitors can also step into an authentic recreation of Rockwell's studio. 9 Route 183, Stockbridge, 413-298-4100.

You don't have to love classical music to visit Tanglewood, the summer home of the Boston Symphony Orchestra. Under Tanglewood's Koussevitzky Music Shed, you can have comfortable seats protected from the elements. But romantic couples often prefer to buy cheaper general admission tickets. That way, the music serves as a serenade to their own summer picnic on the grass. 297 West St, Lenox.

Berkshire Botanical Garden

Take a romantic stroll through one of New England's oldest public gardens. For more than 75 years, lovers of flowers and gardening have found respite and inspiration at the Berkshire Botanical Garden (entrance fee). Among the discrete green spaces are an herb garden, rock garden, and rose garden. There are also gardens dedicated to local luminaries. And depending on when you plan to visit, the Berkshire Botanical Garden may host an event or special exhibition that particularly interests you. The facility is particularly keen on educating visitors about home-grown food. 5 West Stockbridge Road, Stockbridge, 413-298-3926.

Chocolate Springs Café

Scientists believe that the theobromine in chocolate stimulates the pleasure center in the brain. Romantic couples believe that Valentine's Day isn't the only time to break out the brown stuff. In the Berkshires at the Chocolate Springs Café, all forms of the delectable substance are available, including bars, candies, ice cream, and cocoa to drink. We chose ice cream, which was stylishly presented in lacquered Japanese bowls and served with espresso spoons. The only thing missing from our foray to this seductive site was having a private room to paint one another's body with chocolate and lick off the excess. 55 Pittsfield Road, Lenox, 413-637-9820.

McTeigue & McClelland Jewelers

If you appreciate precious stones and settings that transform them into works of enduring art, pay a visit to these Berkshire jewelers. Working with rare stones such as rubies, sapphires, emeralds, tsavorite, and white and yellow diamonds, the experienced staff marries the gems to imaginative settings. Many evoke phenomena of the natural world, others recall vintage mountings, and still others are simply graceful, elegant designs.

An individual planning to pop the question on a romantic Berkshires holiday could not go wrong choosing an engagement ring here (there's even a whimsical "cheapskate" model, which comes with a mini magnifying glass over the small diamond). 454 Main Street, Great Barrington, 800-956-2826.

Crane Museum of Papermaking

Anyone who's shopped offline for wedding invitations or other fine stationery has heard of the Crane brand. At this museum, which is listed on the National Register of Historic Places, visitors can trace the history of American papermaking from Revolutionary days. The museum is open on weekdays from May through August. Free admission. 32 Pioneer St, Dalton, 413-684-6380.

Rouge: A Romantic Restaurant

A favorite with locals and visitors alike, Rouge is a cozy and romantic French bistro in the Berkshires. Diners have a choice of eating at the bar or a table. The New York-trained chef/owner and his wife turn out sophisticated and seductive fare for appreciative guests. Oysters, prix-fixe meals, and desserts are particularly popular. 3 Center Street, West Stockbridge, 413-232-4111.

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THE 10 BEST Couples' Activities & Things to Do in Berkshire

Best things to do in berkshire for couples.

• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• Good for Couples
• Budget-friendly
• Good for Big Groups
• Good for Kids
• Good for a Rainy Day
• Hidden Gems
• Good for Adrenaline Seekers
• Adventurous
• Honeymoon spot
• Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

1. Windsor Castle

2. St. George's Chapel

3. Windsor Great Park

4. Basildon Park

5. Theatre Royal Windsor

6. Windsor & Eton Brewery

7. Stanlake Park Wine Estate

8. Ascot Racecourse

9. The Watermill Theatre

10. Black Park

11. Boulter's Lock and Ray Mill Island

12. Dinton Pastures Country Park

13. Tally Ho Stables

14. Dorney Court

15. Forbury Gardens

16. Welford Park

17. Langley Country Park

18. Kennet & Avon Canal

19. Nature Discovery Centre

20. Royal Ascot

21. Donnington Castle

22. Caversham Court Gardens

23. The Long Walk

24. Hungerford Wharf

25. Feathers and Fur Falconry Centre

26. Combe Gibbet

27. Harris Garden

28. Escape Reading

29. Genting Casino Reading

30. TimeTrap Escape Rooms

What travellers are saying

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• Massachusetts

15 Best Things to Do in the Berkshires

From craft brews to cultural hot spots, the Berkshires has it all.

The Berkshires in western Massachusetts draws in countless visitors every year, thanks to its fascinating history, ample outdoor activities, burgeoning food scene, and incredible shopping. With so many activities to choose from, it can truly delight every type of traveler.

Whether you want to explore its culture at an art museum, sample its refreshing local beverages at a brewery, or head out on a hike for some truly spectacular views, here are some of the best things to do in the Berkshires, no matter the season.

Catch a concert at Tanglewood.

This open-air music venue serves as the summer home of the Boston Symphony Orchestra. While the lush grounds and expansive lawns are open all year round (free of charge), you'll want to plan your trip during the summertime, when you can listen to music under the stars. (Bringing along a delicious dinner and cozy blanket is highly recommended.) Event programming is always rotating , but previous acts include performances from Ringo Starr & His All-Starr Band, James Taylor, the Juilliard String Quartet, and The Black Crowes, to name a few.

Go shopping in Lenox.

Lenox is famous for its charming downtown area dotted with eclectic boutiques and one-of-a-kind shops. Pick up some unique home goods at Annie Selke Shop, Design Menagerie , or MacKimmie Co ; add to your wardrobe with staples from Catwalk Boutique , or Purple Plume ; or grab some vacation reading material (and enjoy a glass of vino) at The Bookstore & Get Lit Wine Bar . Meanwhile, gourmands can peruse the aisles of Oliva Gourmet Olive Oils & Vinegars and Dare Bottleshop & Provisions .

Hike Mount Greylock.

At nearly 3,500 feet tall, Mount Greylock is the highest point in the state of Massachusetts. The entire Mount Greylock State Reservation spans around 12,000 acres. You'll also find several hiking trails, including a stretch of the famous Appalachian Trail. At the summit, visitors can stop at the Veterans War Memorial Tower, a 93-foot granite lighthouse with 89 steps leading to an observation deck. From there, enjoy panoramic views stretching across five states (Massachusetts, New York, Connecticut, Vermont, and New Hampshire).

Eat your way through Great Barrington.

Great Barrington is lined with tasty eats that'll satisfy any craving. Keep it casual at Baba Louie's , famous for its selection of sourdough pizzas. For authentic Mexican staples like mole and margaritas, head straight to Xicohtencatl , which occupies a striking yellow house with a sprawling porch. Prairie Whale is a dinner-only haunt known for its rustic-chic aesthetic, lively ambience, elevated American entrees featuring locally sourced ingredients, and creative cocktails. For a true treat, make a reservation at Number Ten , which serves up all sorts of steaks, poultry, and seafood, plus mouthwatering sides like creamed spinach, mac and cheese, and mashed potatoes.

Check out the Norman Rockwell Museum.

Founded in 1969, the Norman Rockwell Museum in Stockbridge boasts an expansive selection of the artist's work — almost 1,000 original paintings and drawings, to be exact. (Rockwell lived in the town from 1953 until 1978, when he died.) The 36-acre campus is home to 10 galleries, the artist's beloved Stockbridge studio (which was moved here in 1986), and an impressive collection of 100,000-plus items that range from personal calendars to fan mail.

Embark on your own dessert trail.

Grab a sweet treat (or three) at one of several spots in and around the Berkshires. In Pittsfield, indulge in some creamy soft serve at Dairy Cone or homemade cake at Mary's Carrot Cake . Make your way to Lenox to check out the new Sweet Dreams cafe, which sells crowd-pleasing pastries like cinnamon buns and chocolate chip cookies, or the beloved Chocolate Springs Cafe for specially crafted confections like truffles, chocolate-covered pretzels, and marshmallows. Candy lovers of all ages will also appreciate the nostalgia-inducing Robin's Candy , a shop stocked with a curated collection of sweets to suit every palate. Another nearby favorite is the Parisian-inspired Pixie Boulangerie .

Travel back in time at Hancock Shaker Village.

Learn more about Shaker history at Hancock Shaker Village , which dates back to the late 1700s. Today, the site has been transformed into a living history museum with a working farm, a one-mile walking trail, and thousands of fascinating artifacts (think: furniture, tools, textiles, and more). It's also worth noting that Hancock Shaker Village is open seasonally, so plan your visit accordingly.

Get out on the lakes.

Lauren Breedlove/Travel + Leisure

The Berkshires is home to dozens of pristine lakes for swimming, paddling, boating, and fishing. The 511-acre Pontoosuc Lake is among the region's most scenic, and its bright blue waters make it a popular spot for boating. Pack a picnic lunch, some towels, and a chair to lounge on the grassy lawns along the shore. The lake is especially beautiful come fall, when the surrounding trees turn fiery red, orange, and yellow. Meanwhile, Lake Onota is slightly larger at 617 acres. Here, you can relax along the sandy beach area before heading into the water to swim, kayak, or canoe.

Wander through the Massachusetts Museum of Contemporary Art.

The Massachusetts Museum of Contemporary Art (Mass MoCA) offers a whopping 250,000 square feet of gallery space, so be sure to carve out enough time to explore it all. Expect to be dazzled by an array of extravagant masterpieces, including eye-catching ceramics, interactive exhibitions complete with lights and sounds, larger-than-life wall drawings, and striking sculptures.

Get a taste of everything at the Berkshire Museum.

Barry Winiker/Getty Images

Get a little more culture during your visit with a stop at the Berkshire Museum . Here, guests can explore the museum's vast and varied collection of more than 40,000 objects at exhibits, via its digital content, and at community events. And it's truly a place where everyone can find a favorite item. The museum's website explains, its founder, Zenas Crane, was inspired by the American Museum of Natural History, the Smithsonian, and the Metropolitan Museum of Art, and decided to combine all their best attributes into one space, making it possible to see fine art, natural science, and history exhibits under one roof. 

Indulge your bibliophile dreams at Edith Wharton's The Mount.

Courtesy of The Mount

Visitors to the Berkshires can check out  The Mount , the former home of author Edith Wharton, who wrote books like "The Age of Innocence" and "The House of Mirth." The home is now a National Historic Landmark and cultural center dedicated to preserving the space and her legacy. Guests can come to tour the gardens, the home's interiors, and a rotating list of exhibits showcasing both literature and life during the early 20th century. Visitors can even come for a quick ghost tour of the property — if they dare. 

Pluck the perfect apple at Hilltop Orchards.

Courtesy of Hilltop Orchards 

Participate in one of the area's favorite fall pastimes — apple picking — with a visit to  Hilltop Orchards . The farm, located just on the edge of the Massachusetts and New York border, has been a Berkshires institution for more than a century. Guests can pick (and eat) 27 different apple varieties come fall and indulge in a sweet cider donut, too. Not visiting the area during the autumn? No problem — the orchard open year-round and offers cidery tours and tastings, as well as access to its trail system, spread across the 200-acre grounds, which are ideal for hiking in the spring, summer, and fall, and snowshoeing all winter long. 

Seek out more art at The Clark Art Institute. 

Another stellar cultural institution in the Berkshires,  The Clark Art Institute has been open to the public since 1955 and has a dual purpose. As it explains on its website, it's dedicated to the preservation of the classics and is "a distinguished center for research and higher education, dedicated to advancing and extending the public understanding of art." Come explore its permanent and rotating exhibitions, and if you have some extra time, don't forget to marvel at its spectacular 140-acre campus grounds, too. 

Take a ride at the Berkshire Scenic Railway Museum.

Courtesy of Berkshire Scenic Railway Museum

Weave your way through some of the area's most beautiful landscapes with a ride on a historic railway. The museum, founded in 1984, aims to preserve the railway and its history by maintaining historical data and equipment. It also offers visitors the chance to hop aboard for fun seasonal rides. Excursions include a fall foliage trip, a winter Santa train, and more. Check out the  railway's website  to see what's available when you visit. 

Toast to a successful trip.

Cap off a fun-filled trip at one of the nearby breweries, wineries, or cideries. Oenophiles will especially appreciate Balderdash Cellars , where you can lounge on a lawn overlooking a lake. For craft brews, make your way to Wandering Star Craft Brewery , Berkshire Brewing Company , or Big Elm Brewing . Alternatively, if you prefer cider, look no further than the Berkshire Cider Project .

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• 1 Red Lion Inn, Stockbridge, MA
• 2 The Porches Inn, North Adams, MA
• 3 Cranwell Spa & Golf Resort, Lenox, MA
• 4 Brook Farm Inn, Lenox, MA
• 5 Blantyre, Lenox, MA
• 6 Inn at Stockbridge, Stockbridge, MA
• 7 Wheatleigh, Lenox, MA
• 8 The Gateways Inn, Lenox, MA

These 8 Romantic Getaways in the Berkshires are the Perfect Escape

Just 2.5 hours from Boston and three hours from New York, the Berkshires, in western Massachusetts, beckon visitors with their picturesque scenery, excellent hiking trails, rich history, culture, and charming inns. Writers like Edith Wharton and celebrities like Meryl Streep have made homes in this down-to-earth corner of New England, where you can spend mornings ogling contemporary art at Mass MoCA and hiking Mount Greylock in the afternoon. Below, eight of the most romantic inns and resorts perfect for a weekend in the mountains.

An avid Italophile, Laura is always on the hunt for the next great travel trends, luxury hotels, best places to eat and drink, and hidden gems. Her writing has appeared in dozens of publications. She also co-wrote "New York: Hidden Bars and Restaurants," an award-winning guide to the city's speakeasy scene.

See recent posts by Laura Itzkowitz

Red Lion Inn, Stockbridge, MA

One of the most historic hotels in New England, this charming inn in Stockbridge has been hosting guests since before the American Revolution. Its classic New England style is evident as soon as you cross the threshold: antiques, chintz, china, and pewter occupy seemingly every nook and cranny of its lounges and guest rooms. After enjoying classic New England cuisine in the main dining room or the wood-paneled Widow Bingham’s Tavern (think creamy clam chowder, chicken pot pie, or Prince Edward Island mussels), head downstairs to the Lion’s Den—the inn’s underground pub—where you can listen to live music seven nights a week.

The Porches Inn, North Adams, MA

Sister property to the Red Lion Inn, the Porches Inn in North Adams offers modern accommodations in seven renovated Victorian buildings. Its location right across the river from Mass MoCA makes it ideal for culture vultures who made the pilgrimage to see the mill-turned-museum's incredible wall drawings by Sol Lewitt and massive installations by German sculptor Anselm Kiefer. The creativity continues inside the inn, which has an artist-in-residence program, vintage plates, and paint-by-number artwork. In summer, you can hike nearby Mount Greylock, the highest mountain in Massachusetts.

RELATED: Your Perfect Guide to the Berkshires: Where to Stay and What to See

Explore More: See hotel details | See all North Adams, MA hotels

Cranwell Spa & Golf Resort, Lenox, MA

The highlight of this Gilded Age resort , built around a historic Tudor-style mansion, is dining at the award-winning restaurant Wyndhurst at the Mansion. There, American classics are served in an elegant dining room with panoramic views of the Berkshires from the Rose Terrace. Rooms and suites are done up in a classic style, with some suites boasting fireplaces, marble bathrooms, and four-poster beds. Relax at the spa—one of the largest in the northeast—then venture out into the charming town of Lenox, where you can visit the Mount (Edith Wharton’s estate) and attend concerts by the Boston Symphony Orchestra at Tanglewood .

Explore More: See hotel details | See all Lenox, MA hotels

Brook Farm Inn, Lenox, MA

This historic B&B in Lenox has played host to literary luminaries including Pulitzer Prize-winning poets, so it’s no wonder you’ll find a cozy library. The design is very granny chic, with antique furniture, dainty floral wallpaper, and doilies aplenty in the individually decorated rooms. In winter, you can warm up by the fire, while in summer the pool is the perfect place to take a dip. Yogis can take private lessons on the property or enroll in classes at the nearby Kripalu Center for Yoga & Health .

RELATED: New England's Most Adorable Bed and Breakfasts

Blantyre, Lenox, MA

Housed on the sprawling estate built in 1902 for Gilded Age millionaire Robert Patterson, this gorgeous hotel outside Lenox recently received a multi-million-dollar renovation and was reborn as a Relais & Châteaux property. Named for the Scottish estate where Patterson’s mother was raised, it resembles a Scottish glen with ivy-clad brick walls, mullioned windows, slate-roofed turrets, and bucolic gardens. Luxury seekers will love the Dom Pérignon salon—the first such year-round lounge in the U.S.—and foodies should be sure to make a reservation for the chef’s tasting menu for a romantic dinner.

Inn at Stockbridge, Stockbridge, MA

Guests of this charming inn in Stockbridge rave about the warm welcome from innkeepers Lisa and Jeff, who prepare a homemade breakfast every morning and will make your stay extra special with chilled champagne and fresh-cut flowers upon request. Individually decorated rooms are spread out among a main house, cottage suites, and four barn suites, which feature whirlpool Jacuzzis. Bonus: the location puts you within easy reach of nearby hiking trails, the Norman Rockwell Museum , and other Berkshires attractions.

RELATED: 12 Best Inns in the U.S.

Wheatleigh, Lenox, MA

Want to play Gatsby for a weekend? This grand estate , built in 1893, was a wedding present for a Gilded Age tycoon's daughter. The Florentine Renaissance-style mansion sits on 22 acres of grounds designed by Frederick Law Olmstead (the man behind New York’s Central Park). Now a member of Leading Hotels of the World, the intimate property has just 19 rooms and suites, a heated outdoor pool, tennis court, sculpture garden, and three restaurants and bars including The Portico by Jeffrey Thompson, an elegant fine dining restaurant in an enclosed glass colonnade with just eight tables.

The Gateways Inn, Lenox, MA

This award-winning B&B was originally built as the summer cottage for Harley Proctor of Proctor & Gamble fame. The 11 rooms are all individually designed—some have fireplaces and hardwood floors; others come with antiques and marble bathrooms. After dinner (the restaurant serves contemporary American fare in a laid-back atmosphere), pull up a stool at the custom-built mahogany bar and listen to live jazz in the lounge. Looking to take in the fresh mountain air? The Gateways is within striking distance of Mount in Lenox and the Hancock Shaker Village in nearby Pittsfield.

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15 Best Things To Do in The Berkshires

Updated May 11, 2022

The Berkshires region of western Massachusetts is known for its outdoor adventures like hiking and water sports, as well as cultural experiences. Home to several performance centers, including Tanglewood and Jacob's Pillow , the Berkshires offers

• All Things To Do

Tanglewood Tanglewood

The summer home of the Boston Symphony Orchestra, this open-air music venue attracts thousands of visitors who come to enjoy a variety of classical, contemporary, jazz and pop music performances every year. The Boston Symphony Orchestra has spent its summers at this grand estate located between the towns of Lenox and Stockbridge since 1937. Over this time, many renowned artists have also made appearances at the venue, including Yo-Yo Ma, Earth, Wind & Fire and Steely Dan. Tanglewood is most popular during the summer when the weather allows for sitting on the property's large lawn during performances. Still, the grounds also house multiple indoor facilities and restaurants, which enable visitors to enjoy programs, galas, events and cocerts year-round.

Reviewers call Tanglewood a "music lover's paradise," with charming scenery that keeps travelers returning year after year. Visitors appreciated the well-manicured grounds and world-class concerts, but recommend bringing your own lawn chairs, food and drinks to avoid the hefty prices of concession trucks, restaurants and stores on the property. Whether you bring your seating or rent from the facility, friendly staff can help you get situated, according to reviewers.

Jacob's Pillow Jacob's Pillow

Follow the sounds of dancing feet to the Berkshires' 225-acre National Historic Landmark, Jacob's Pillow. A recipient of the National Medal of Arts, Jacob's Pillow is home to one of the most renowned dance training centers in the nation as well as the longest-running international dance festival. The festival, which takes place from mid-June to the end of August, hosts more than 50 dance companies and 500 free performances, talks and events.

Audiences love watching performances with the backdrop of the picturesque Berkshires. Reviewers appreciate the pre-show talks that explain the upcoming performances' background and meaning. What's more, visitors are permitted to bring their own picnics and wine to avoid the expensive prices at the on-site restaurants. However, visitors who indulged in a meal at the property's Old Inn On The Green say it is worthwhile.

Monument Mountain Monument Mountain free

Follow in the footsteps of literary legends Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes with a hike up Monument Mountain. Calling the town of Great Barrington home, Monument Mountain brims with history and striking views that overlook the Housatonic River Valley and Mount Greylock . Come prepared with your walking shoes and water – it takes some endurance to tackle the 720-foot elevation gain on the way up to Monument Mountain's 1,642-foot Squaw Peak.

Outdoor enthusiasts who visit the Berkshires will appreciate the mountain's various trails, which range in difficulty. If you're looking for a leisurely climb up, take the Indian Monument Trail – a 1 1/2-mile path that climbs the west face of the mountain. For the most direct route, take the Hickory Trail, which measures less than a mile, but is considered the most strenuous. As you make your ascent, heed the advice of recent visitors and take in these views with a mid-hike picnic.

Mount Greylock Mount Greylock

Mount Greylock boasts the highest point in the state of Massachusetts. Located in the town of Adams, its summit reaches 3,491 feet. On a clear day, visitors to the summit can see as far as 90 miles. The area offers a variety of seasonal activities, including hiking, camping, hunting, snowmobiling, skiing and educational programs led by local park rangers.

Recent travelers said Mount Greylock is a great excursion because it caters to hikers of all levels thanks to a variety of trails. Helpful and friendly recommendations by the rangers at the visitor center were also appreciated and added to the quality of hikers' experiences. Reviewers agree that the views are worthwhile, whether you're taking the scenic driving route or tackling one of the many hiking trails. At the peak, travelers appreciated the touching Veterans War Memorial Tower and a meal at the Bascom Lodge . Past visitors recommend making a reservation to avoid waiting once arriving at Mount Greylock's summit for a sunset dinner.

Clark Art Institute Clark Art Institute

The Sterling and Francine Clark Art Institute in Williamstown displays exhibits featuring collections of European and American paintings, sculptures, drawings, photographs and other unique forms of art ranging from the Renaissance to the early 20th century. You can observe masterpieces throughout the museum on your own or download a multimedia guide to your smartphone (for an extra fee) to virtually walk you through exhibitions. Outside the museum, you'll find picnic tables and nature trails.

Recent visitors expressed excitement about the wide range of world-class displays within the museum. They also suggested picnicking by the reflecting pool followed by a scenic stroll on the campus trails outside the Clark. Reviewers also appreciated that the museum offers something for everyone thanks to its diverse and ever-changing exhibits.

The Mount The Mount

Once the home of author and humanitarian Edith Wharton, this Lenox estate includes a 42-room country house and formal gardens that span nearly 50 acres. Wharton's home and gardens teem with stories of her vibrant life, philanthropic work and literary legacy. House and garden tours offer visitors a glimpse into the author's past, while the seasonal "Backstairs" tour provides a behind-the-scenes look at the servants who lived at The Mount. Ghost tours are also available from July to October. Visitors at The Mount will also find a terrace cafe, a bookstore, forest hiking trails and a cultural center, which plays host to a variety of community events.

Visitors applaud the entertaining and informative guides, who they say bring Wharton to life. Reviewers suggest setting aside several hours to tour the property and gardens, as you'll want to take your time admiring the estate.  

Pleasant Valley Wildlife Sanctuary Pleasant Valley Wildlife Sanctuary

Located in the town of Lenox, this 1,211-acre wildlife sanctuary run by the Massachusetts Audubon Society features 7 miles of trails, a large pond, and striking views of forest, meadows, wetlands and wildlife. There are many well-marked walking trails to explore, which range in length and difficulty. The All Persons Trail fits its title as a mostly flat and 30- to 40-minute easy loop around Pike's Pond where hikers can often spot beavers. For the more adventurous, the Trail of the Ledges is a 3-mile loop that challenges visitors to hike a steep vertical to the top of Lenox Mountain, which reaches an elevation of 2,126 feet. The strenuous hike up is well worth the vistas of Mount Greylock , the Taconic Range and the Catskill Mountains. What's more, Pleasant Valley offers many different programs for people of all ages and abilities, including birding, canoeing, paddling and more.

Visitors say there are so many hiking loops to choose from that it would simply be impossible to do them all in one day. Luckily, the staff in the nature center can help groups decide which trails would suit them best and where they might find beavers along the way.

Jiminy Peak Mountain Resort Jiminy Peak Mountain Resort

This four-season resort in the town of Hancock is constantly bustling with visitors eager to try its many activities. The largest ski and snowboard resort in southern New England, Jiminy Peak offers a variety of winter sports, including snowshoeing, and lessons for all ages and levels. As the snow melts away, Jiminy Peak transitions into a summer mountain adventure park. Among the attractions are an alpine slide, a scenic chairlift ride, a rock climbing wall and the self-guided Aerial Adventure Park, which features six elevated courses. Plus, several hiking trails offer views of Mount Greylock and the Jericho Valley. Families with children enjoy spending time at this resort together. Recent travelers applauded the wide range of activities for children and adults and the reasonable prices.

The resort is open year-round, but hours for each activity and facility can vary. Prices for the adventure park and ski lift also vary based on age, time and activities. For information on pricing, visit the Jiminy Peak website .

Herman Melville's Arrowhead Museum Herman Melville's Arrowhead Museum free

Restored by the Berkshire County Historical Society, the home of "Moby-Dick; or, The Whale" author Herman Melville is open to visitors interested in learning more about the literary legend. Located in the historic town of Pittsfield, the house was inhabited by Melville from 1850 to 1863. Along with the home, visitors can tour the barn and surrounding grounds, which feature a farm and nature trail.

Even some of Melville's biggest fans said they were surprised at the amount of new information they learned during their tours. Recent visitors appreciated the interesting stories shared by the site's knowledgeable tour guides, as well as the gift shop, which sells a variety of books about and written by Melville.

Ramblewild Adventure Park Ramblewild Adventure Park

The Berkshires offers plenty of hiking opportunities to get your bearings on the ground, but Ramblewild Adventure Park enables visitors to experience the Massachusetts mountains from an entirely different altitude. This treetop adventure course challenges outdoor adventurers and beginners alike as they climb and weave through the obstacles in the hemlock groves of Feronia Forest. Ropes, ladders, bridges, swings and zip lines are among the 130 elements across the eight different routes that await visitors 45 feet above the forest floor. Along with its aerial park, Ramblewild also offers hiking trails and snowshoeing.

Previous travelers visiting Ramblewild as a family say the aerial course is among the best things to do in the Berkshires. Reviewers credit the encouraging staff and breathtaking views as prime reasons to plan a trip. Visitors also appreciate the range of courses for all skill levels. Reviewers say the 3 1/2-hour timeslot enables visitors to try out a handful of courses and take in the landscape from different parts of the forest, all while getting a great workout.

Massachusetts Museum of Contemporary Art Massachusetts Museum of Contemporary Art

The Massachusetts Museum of Contemporary Art (MASS MoCA) in the town of North Adams features impressive visual and performing arts from both well-known and emerging artists. The diverse artwork including everything from sculptures to virtual reality to painting to photography. What's more, the museum hosts more than 75 performances year-round, ranging from contemporary dance to outdoor silent films with live music. Whether you're looking to see art or make art, the MASS MoCA is sure to fuel your creative mind.

Travelers say this industrial museum is a work of art in itself. This unique space offers so much eclectic artwork that reviewers report wandering its halls for hours. Visitors are especially impressed with the thought-provoking contemporary artwork and how each exhibit is strikingly different from the last, making for a memorable experience.

Norman Rockwell Museum Norman Rockwell Museum

The Norman Rockwell Museum walks visitors through the life and prolific works of the well-known American artist. Located in Stockbridge – the town Rockwell called home for the last 25 years of his life – the museum features a variety of exhibits displaying the artist's work, as well as his studio. In the museum cottage and surrounding grounds, festivals, workshops, speakers and galleries take place regularly.

Reviewers recommend tagging along on a tour, in which knowledgeable guides give thoughtful insight into the painter and his artwork. Recent visitors also suggested strolling the attractive grounds and having a picnic instead of eating the meals offered on-site. Stockbridge is home to many fresh and locally-sourced restaurants; the famed Red Lion Inn is just down the street.

Naumkeag Naumkeag

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Hancock Shaker Village Hancock Shaker Village

Berkshire Botanical Garden Berkshire Botanical Garden

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• 33 Best Things to Do in the Berkshires

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What are the best things to do in the Berkshires? This part of Western Massachusetts is so special — not just beautiful, but idyllic, like a painting; not just interesting, but one of the most fascinating regions in the state.

Most people come to Massachusetts to visit Boston, or Cape Cod, or Martha’s Vineyard or Nantucket. But there are treasures waiting for you if you’re willing to head out west.

Despite growing up in Massachusetts, I’ve barely seen the Berkshires — I went to summer camp in East Otis for a few years, but that’s it. And I know it’s human nature not to visit what’s right in front of you. You always assume you’ll be able to do that someday, so why do it now?

But in 2021, a time when people have been looking to closer, local getaways, I decided it was time to visit the Berkshires — not only to have fun, but to research extensively, and eventually create guides like this one to help you plan your own trips to the Berkshires.

Did my trip go well? OH, IT DID! I had the best time in the Berkshires — and I can’t wait to show you all the best things to do here.

I would like to acknowledge and honor the Mohican, Wabanaki and Pocumtuc people, the Indigenous stewards and traditional owners of the unceded land now known as the Berkshires.

This post was last updated in June 2021.

Table of Contents

Why Travel to the Berkshires?

The Berkshires are famous for lots of things — Tanglewood, the summer concert series in Lenox . Canyon Ranch, the fancy spa. Art museums and dance and live theater, all set on a mountainous landscape, evergreen forests crisscrossed with country roads.

But the Berkshires aren’t just for rich people doing fancy things. They’re for everyone. There’s lots to see and do in the Berkshires, including lots of low-key activities — and you’re only a few hours from either New York or Boston.

Where the Berkshires excel, in my opinion, is being both an outdoor destination and an arts destination. You can end up fitting a lot of variety into a short getaway.

I know a lot of couples where one person is into the arts and the other is more into the great outdoors. Often, planning a trip for these kinds of couples means someone is always compromising. But some destinations blend culture and nature seamlessly! Like Asheville, North Carolina , or Oaxaca, Mexico , the Berkshires are perfect for travelers who want to mix the outdoors and the indoors on their trip.

Most people drive to the Berkshires, and you need a car to explore the area sufficiently. If you’re flying in, the Albany airport is about 45 minutes away.

Head outside! A lot of outdoor sites like Bash Bish Falls for free; the Berkshire Botanical Garden is free on Tuesdays; get the best $1 cider donuts of your life at Hilltop Orchards, explore the towns, check out cool coffeeshops like Six Depot Roastery.

If you’re looking to attend concerts, shows and events, aim for summer . Fall is gorgeous but very busy; late spring is another good choice.

The three best museums in the Berkshires are the Norman Rockwell Museum in Stockbridge, the Clark Institute in Williamstown, and MASS MoCA in North Adams.

Where are the Berkshires?

The Berkshires are located in Western Massachusetts. Berkshire County is the westernmost county in Massachusetts; anything within Berkshire County is considered “the Berkshires.”

It feels like the Berkshires are comprised of a southern part and a northern part. In the southern portion, popular towns to base in include Stockbridge , Lenox , and Great Barrington. This is the classic small town Berkshires area that most people have heard of.

The northern portion includes towns like North Adams, Williamstown, and Pittsfield. It’s a different feel up here — more urban, not quite as photogenic — but still very much worth visiting.

Even so, the Berkshires are small enough that you can base in one part and explore the whole region. The drive from Great Barrington in the far south to North Adams in the far north, for example, takes just over an hour.

Even so, culturally speaking, people from the north don’t always go south and vice versa. One local told me people from Pittsfield see going to Stockbridge as something you do for a special occasion — even though it’s less than 30 minutes away.

On my trip, I wanted to get to know all of the Berkshires in depth — so I split my time between two bases, Stockbridge in the south and North Adams in the north. More on where I stayed below.

Read More: The Best Towns in the Berkshires

Berkshires Map

The map above is a complete guide to the Berkshires, including everything mentioned in this post, color-coded based on the type of destination. Hope it helps you get the lay of the land.

Best Things to Do in the Berkshires

Some of my friends go to the Berkshires to get away from busy city life. They rent a cabin on a lake, read books, hit up the farmers’ markets, and grill.

That’s a nice way to spend a weekend — but the Berkshires are SO much more than a quiet place to unwind. There is an insane number of things to do in the Berkshires!

I’ve broken it down into four categories: arts and culture, outdoor activities, historic sites, and food and drink.

Arts and Culture in the Berkshires

Don’t even think of planning a trip to the Berkshires without taking in the arts and culture! Whether you’re looking for museums or performing arts, there is so much to enjoy here. Though if you’re here for performances, you should try to time your trip for the summer months.

Norman Rockwell Museum

Norman Rockwell is famous for his scenes of small-town New England, and many of those scenes come from the town of Stockbridge, where he made his home. The Norman Rockwell Museum is a comprehensive collection of his art, from the 300+ Saturday Evening Post covers to his personal items, larger works of art, and works by other artists inspired by him.

I love deep dives into a single artist, watching their work evolve over time. What I especially loved about this museum is how they showed Rockwell’s journey to activism, including the work that went into his portrait of Ruby Bridges, The Problem We All Live With .

Admission to the Norman Rockwell Museum is $20 for adults, $18 for seniors and veterans, and free for active military and children under 18.

If you know anything about the Berkshires, you’ve probably heard of Tanglewood ! This venue in Lenox is the summer home of the Boston Symphony Orchestra, and performances are in a theater that opens to the great outdoors, letting people enjoy outstanding music under the stars.

Each summer, you can experience the Boston Symphony Orchestra, the Boston Pops, the Tanglewood Music Center, and more. (One of the most popular events is John Williams night, which some of my friends go to see every year!)

See the full schedule of Tanglewood performances here.

Clark Institute

Did you know that the Berkshires are home to one of the best collections of Impressionism in the world? I had no idea! The Clark Institute in Williamstown is a museum featuring American and European art from the Renaissance through the early 20th century.

Most impressive, though, is their massive collection of Renoir paintings. I felt as if I were in Paris. What a special find this place is.

There are rotating exhibits throughout the year, and be sure to leave enough time to explore the trails outside, many of which lead to even more sculptures.

Admission to the Clark Institute is $20 and free for students with ID and children under 18. The outdoor walking trails are free to all.

Shakespeare and Company

If you’re in the mood for some classic theater, Shakespeare and Company performs the Bard’s shows in Lenox all summer long, and other plays throughout the year. In addition to the performances, Shakespeare and Company does some of the best theatrical training in the region.

See the full schedule of Shakespeare and Company performances here.

Mass MoCA — the Massachusetts Museum of Contemporary Art — is one of the most imaginative and stunning museums in Massachusetts, as well as an inspiring story of reinvigorating the former mill town of North Adams. The ever-changing exhibits here are intended to cover every medium and break conventional boundaries.

The museum is in the former Sprague Electric Company, now an expansive building filled with light from every angle. Plan to spend a lot of time here, because the campus has everything from an ice cream shop to a craft brewery! Plus, you never know which works of art will end up captivating you.

Modern art isn’t for everyone — but I bet you’ll enjoy this place, as it’s genuinely one of the best things to do in the Berkshires.

Admission to MASS MoCA is $20 for adults, $18 for seniors and veterans, $12 for students with ID, $8 for age 6-16, and free for children under 6.

Williamstown Theater Festival

If you’re looking for both classic and cutting-edge theatrical performances, be sure to check out what the Williamstown Theater Festival has to offer during the summer months. (Yes, they call themselves WTF!)

This regional Tony award-winning festival features all kinds of shows and events in this little northwest corner of Massachusetts, from educational workshops to late-night cabarets.

See the full schedule of Williamstown Theater Festival performances here.

Berkshire Museum

If you’re looking to explore more of what makes the Berkshires what they are, look no further than the Berkshire Museum in Pittsfield. This museum has sections on the science, ecology, history, and culture of the Berkshires.

Many of the exhibits are more oriented toward kids — like the aquarium and animals in miniature section — but I did love the Feigenbaum Hall of Innovation, which profiles different notable residents of the Berkshires, like W.E.B. DuBois and Susan B. Anthony.

Admission is $13 for adults, $6 for ages 4 to 17, and free for children under 4.

Jacob’s Pillow

You’ve got your music, you’ve got your theater — why not add some dance into the mix? The Berkshires are home to Jacob’s Pillow, a National Historic Site in Becket home to the nation’s longest-running dance festival. Each summer, Jacob’s Pillow hosts more than 50 dance companies for live performances, as well as talks, workshops, and more.

From classic performances to more avant-garde offerings, Jacob’s Pillow is a must during the summer if you’re a dance fan.

See the full schedule of performances here.

Williams College Museum of Art

Set on the idyllic Williams College campus, the Williams College Museum of Art features exhibits by emerging artists from all over the world.

The museum is currently closed due to COVID, but we hope it will open soon. Admission is free.

Outdoor Activities in the Berkshires

You don’t need to be a hardcore athlete to enjoy the outdoors in the Berkshires. If you’d like a simple and easy outdoor activity, head to the Berkshire Botanical Garden. If you’re a hardcore hiker, Mount Greylock is calling your name! And if you’re a novice hiker who would like an easy walk through the woods with a beautiful waterfall, you can’t beat Bash Bish Falls .

Bash Bish Falls

I know, your mind wants it to be “Bish Bash Falls” but it’s actually “Bash Bish Falls”! This is the kind of hike that I love — it’s easy, not too long, and there’s a big payoff at the end. I think it’s one of the best free things to do in the Berkshires.

This waterfall is in Bash Bish Falls State Park in the southwest corner of Massachusetts — but you can actually hike there from either the Massachusetts side or Taconic State Park on the New York side. The hike from the Massachusetts side is shorter (0.6 miles or one hour return) but steeper; the hike from the New York side is longer (1.5 miles or 90 minutes return) but not as steep.

Since I didn’t have my hiking shoes with me, I chose to hike from the New York side — and I loved the novelty factor of walking from one state into another! What a lovely way to spend the morning, having been fortified with a pastry from Berkshire Mountain Bakery.

Keep in mind that you’re not allowed to swim in the falls. But I bet you’ll be satisfied even without a dip in the river.

Admission is free.

Berkshire Botanical Garden

Located right in Stockbridge, the Berkshire Botanical Garden is one of the oldest display gardens in the Northeast US. The garden displays all kinds of interesting plants from all over the region, all landscaped beautifully and designed to teach you more about them.

If you’re looking for a casual stroll while enjoying the beauty of nature, this is a great option. (And if you’re here on a Tuesday, you can take advantage of free admission!) The garden also puts on events like toga and tai chi classes among the flowers, workshops, receptions, and even classes in watercolors and birding.

Admission to the Berkshire Botanical Garden is $15 for adults, $14 for seniors, and free for children under 12. Admission is free to all on Tuesdays.

Berkshire Camino Guided Hikes

If you’re looking for a guided hike with a twist, take a look at Berkshire Camino — a hiking company inspired by the Camino de Santiago, the life-changing pilgrimage across Spain. Owner Mindy Miraglia loved her time on the Camino and today she brings Camino magic to small hiking tours in the Berkshires.

The Camino is all about hiking from one town to the next, and discovering what lays before you. That’s how these hikes are structured — you could start out in Housatonic and hike to Stockbridge, or maybe start in Lee and hike to Lenox. There are shorter walkabout-style hikes within towns, too.

Berkshire Camino has walkabouts from $18 per person, half day hikes from $80 per person or $150 for two people. Multi-day hiking trips are available, too.

Mount Greylock

If you’re looking for a bigger challenge, consider hiking Mount Greylock — the highest point in Massachusetts! Mount Greylock State Reservation, near Adams, is home to more than a dozen hiking trails, ranging from “easy” to “aggressive.” Hiking to the summit of Mount Greylock is one of the most strenuous routes.

Even if you’re not up for a tough hike, you can still enjoy one of the easier hikes while taking in the gorgeous scenery.

Admission to Mount Greylock State Reservation is free; parking is $5 for Massachusetts residents and $20 for those from out of state. See the full hiking guide here.

Ashuwillticook Rail Trail

Don’t you love when old railroad tracks are repurposed into something better? The train tracks here fell into disuse in 1990, so they turned it into a 10-foot-wide paved trail, running from Cheshire to Lanesborough to Adams. Throughout the rail trail you get to enjoy views of the Hoosic River, mountains, and lakes — and if you’re here for the fall foliage, even better!

If you’re bringing your bike to the Berkshires — or even your skateboard or rollerblades — this would be my top recommendation for you. But even if you’re just here to walk or run, it’s a lovely place to enjoy a bit of nature in between all your museum-hopping.

The Ashuwillticook Rail Trail is free and there are several free parking lots along the trail.

Housatonic River Walk

You’ll see the Housatonic River winding throughout the Berkshires, but perhaps its best segment is in Great Barrington, where they’ve created the Housatonic River Walk . Signs direct you between two private homes and suddenly you’re on a beautiful path along the river.

There are two segments of the River Walk — you can see them on a map here — and there are displays at the entrances that tell you more about what you’re seeing.

Great Barrington is probably the best town in the Berkshires to spend an afternoon exploring the shops and downtown. But nothing delighted me more than the River Walk!

The Housatonic River Walk is free.

Pontoosuc Lake

I was driving through Pittsfield and admiring a lake in the distance — then I saw a parking lot leading to lakeside picnic tables. I had to stop and visit! Pontoosuc Lake is divided between Pittsfield and Lanesborough, and it’s a lovely place for a quick stop.

This lake is more popular for boating and fishing than swimming, and boat rentals are available. If you’re spending time in the Pittsfield area, you may want to check out the Pittsfield National Forest as well.

Pontoosuc Lake is free.

Monument Mountain

One of the more stunning hikes in the Berkshires is up Monument Mountain in Great Barrington. There are three trails leading to the summit, all under three miles. In addition to stunning views of the rocky mountain and expansive landscape, you might see hawks or bald eagles!

Fun fact: authors Herman Melville and Nathaniel Hawthorne met while sheltering from a storm while hiking Monument Mountain — and became friends for life. Melville even dedicated Moby-Dick to Hawthorne. (You are constantly reminded of this in the Berkshires!)

Admission to Monument Mountain is free; parking is $6.

Natural Bridge State Park

North Adams might be known as the funky art town, but they also have one of the nicer state parks in the region: Natural Bridge State Park. This park is home to the only natural white marble arch in North America — which was formed 550 million years ago!

If you’re a geology fan, this is the park to visit. It’s remarkable seeing how the water carves around the stones. You can hike through a white marble quarry — also the only one in North America.

Admission to Natural Bridge State Park is free. Parking is $5 for Massachusetts residents and $20 for those from out of state.

Pleasant Valley Wildlife Sanctuary

One of the hidden gems of the Berkshires is the Pleasant Valley Wildlife Sanctuary — 1,000 acres of forest, meadows, wetlands, and mountain slopes, right on the edge of Lenox. Run by the Audubon Society, this is home to some of the best wildlife watching in the region, from beavers to birds.

Some of the highlights are a challenging hike to the summit of Lenox Mountain; an All Persons Trail, a universally accessible trail with Braille, audio, and tactile descriptions; and an active beaver colony that can be viewed from Pike’s pond.

Admission to Pleasant Valley Wildlife Sanctuary is $5 for adults, $3 for seniors, and $2 for children age 2-12.

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort is a great spot for mountain fun in the Berkshires. This family-friendly park has everything from Alpine slides to mountain coasters, a giant swing, chairlift rides, a rock climbing wall, a bungee trampoline, and more.

Coming in the winter? They have plenty of skiing.

For those over 54 inches, summer admission to Jiminy Peak is $59 for six hours and $39 for four hours. For those who are 38-53 inches, summer admission is $49 for six hours and $29 for four hours. Buy online ahead of time because there is a $5 per ticket surcharge if you wait to buy at the door.

Skiing in the Berkshires

If you’re up for a winter visit, the Berkshires have a lot of places to ski. In addition to Jiminy Peak Mountain Resort , check out Ski Butternut , Otis Ridge , Bousquet Mountain , and Berkshire East .

Historic Sites in the Berkshires

For centuries, the Berkshires have been a draw for artists, writers, and creatives of all types. It didn’t hurt that it made a peaceful retreat that wasn’t too far from both New York and Boston!

Fed up with the snobbery of Newport, Rhode Island, literary legend Edith Wharton decided to move to the Berkshires in 1901. Her home in Lenox was christened The Mount , she spent many of her most prolific writing years here, and today it’s one of the most stunning historic homes in the region.

Wharton had a lot of style — and I found myself longing for her furnishings! She actually had a pale pink dining room with fuchsia and gold cutlery! The house is a remarkable portrait of how the wealthy lived during this time period, and it makes you think about how idyllic surroundings can inspire you as an artist.

Admission to the Mount is $20 for adults, $18 for seniors, $13 for students with ID, and free for children under 18. The grounds are free.

Ventfort Hall

Also in Lenox, Ventfort Hall is an imposing mansion built in 1893 for Sarah Morgan, sister of J.P. Morgan. Today it’s a fully furnished home that doubles as the Museum of the Gilded Age. It’s designed in a sumptuous manner teaching you how people lived in this interesting point in time.

I found the guides here to be excellent, passionate and well-versed in the history and architectural quirks of this property. Good guides definitely make you more excited about a place!

Most people will tell you that The Mount is the best historic home in the Berkshires — but I had so much affection for Ventfort Hall.

Admission to Ventfort Hall is $18 for adults, $17 for seniors, $10 for students age 18-23 with ID, and $7 for age 5-17, and free for children under 5.

Red Lion Inn

Everyone in the Berkshires knows all about the Red Lion Inn in Stockbridge — even casual Berkshires visitors are well versed in it. The Red Lion Inn was first established as a tavern in 1773, and though it’s gone through various iterations since then, that makes it one of the oldest continuously operated inns in the United States.

It’s a piece of living history, and it’s an interesting place to walk through and enjoy the decor of centuries past.

I stayed at the Red Lion Inn for part of my trip ( more on that below ), but you don’t have to be a hotel guest here to enjoy it. Enjoy a glass of wine at the Lion’s Den pub, eat at the restaurant (one of the few places in Stockbridge open on a Tuesday, I learned!), or simply stake out one of the rocking chairs on the front porch.

Chesterwood

You may not know artist Daniel Chester French off the top of your head, but you definitely know his work — he created the Lincoln Memorial. Today, his legacy lives on at Chesterwood , his home in Stockbridge, where you can visit his studio and learn more about his life and work.

French considered the Berkshires his personal heaven and spent the six warmer months of the year living here, enjoying views of the mountains and creating smooth, sumptuous sculptures. I highly recommend taking the guided tour so you can learn more about his life and work.

Honestly, much of his life was similar to artists today — like when he did a job for free because they promised him paid work in the future — and then they gave him nothing. His friend Ralph Waldo Emerson bullied them into paying him!

Admission to Chesterwood is $20 for adults, $18 for seniors, $15 for active military or veterans, $10 for young adults age 13-21, and free for children under 13.

The most difficult thing about Naumkeag may be pronouncing it (hint: it’s nom-keg , and it helps to picture an animal nomming on a keg of beer). This historic shingle-style home has 44 rooms and was home to generations of the Choate family. While the inside is interesting to explore, the gardens are the big draw here.

You can enjoy sumptuous flower gardens, quintessential Berkshires views over the countryside, and even a Chinese-style garden. I recommend pausing to get a beverage while sitting in Adirondack chairs looking over the landscape.

Admission to Naumkeag is $10 for adults, $15 for seniors and students with ID, $5 for children 3-12, and free for children under 3.

Hancock Shaker Village

The Shakers were a fascinating sect within American society, and their legacy lives on at the Hancock Shaker Village in Pittsfield, a historic center and working farm. The Shakers believed in communal life, celibacy, confession of sin, racial and gender equality, simplicity, and pacifism.

In this village, you can see the homes that were divided into the men’s area and the women’s area (and yes, the celibacy is why they died out!), and you can learn about how they lived self-sufficiently on this farm, growing food, raising animals, and producing crafts. It’s an interesting look into a group that gets little attention outside history classes.

Admission is $20 for adults; $18 for seniors, AAA members, MTA cardholders, and active and retired US military; $8 for youth age 13-17; and free for children under 13.

When you picture the home of Herman Melville, what do you imagine? Somewhere set on a cliff overlooking a stormy sea? You’re probably not picturing a yellow house with a red barn in the Berkshires, overlooking Mount Greylock in the distance! Melville moved to Pittsfield in 1850 to write in solitude; he lived at Arrowhead for 13 years. While here he wrote some of his best works, including Moby-Dick .

To see the house itself, you go on a guided tour and learn all about Melville’s history and his life in the Berkshires. If you’re a Moby-Dick fan, this is a place you should prioritize.

Admission to Arrowhead is $16 for adults, $14 for seniors, $10 for students, and free for children under 13.

Food and Drink in the Berkshires

You might not think of the Berkshires as a culinary destination — but wait until you see what this place has to offer! Some of my favorite experiences in the Berkshires involved the fabulous local cuisine.

Be sure to double-check the opening hours, because many places are closed Monday through Wednesday.

Farm to Table Dining in the Berkshires

One nice thing about visiting the Berkshires is that so many restaurants serve farm-to-table cuisine. Here are some notable ones worth visiting:

The Prairie Whale in Great Barrington , a funky and welcoming restaurant in the Brooklyn of the Berkshires, serves products from their farm in nearby Monterey. Don’t be afraid to try the pig head rillette.

Mezze Cafe + Bar in Williamstown originally served Mediterranean small plates — but has since grown to offer dishes of all sizes with New England ingredients.

The Old Inn on the Green in New Marlborough is a bit of the beaten path but well worth the stop — especially for the Sunday-Wednesday-Thursday prix fixe menu, with three locally sourced courses for just $46.

John Andrews Restaurant in South Egremont , located in an 18th century farmhouse, has been doing farm-to-table menus since 1990. They serve original dishes from artisan producers and grow quite a bit in their garden.

cafeADAM in Great Barrington not only makes use of local producers and dishes — they also feature locally foraged ingredients, like mushrooms from Chef Adam’s secret spot.

The Old Mill in South Egremont features New England ingredients interpreted into new and exciting dishes — and has a commitment to using only wild or organically farmed seafood.

Berkshire Mountain Bakery

If you’re looking for some excellent baked goods, I recommend stopping at Berkshire Mountain Bakery in the tiny town of Housantonic. (It also makes a great stop on the way to Bash Bish Falls, I found out!) This small bakery specializes in sourdough and high-end bakeries, and people from all over the region drop by to pick up loaves of bread.

I grabbed a Kouign-Amann (because I’m fancy — or, really, because I watch the Great British Bake-Off) and it was everything that pastry should be: soft but strong, flaky, covered with sugar.

There is a second location in Pittsfield that doubles as a pizza cafe! And if you really miss the bread, they deliver within the US.

Six Depot Roastery and Cafe

Some coffeeshops are worth going out of your way — and Six Depot Roastery and Cafe in West Stockbridge is well worth the visit. This cafe takes coffee and tea SO seriously. They only serve coffee from sources around the world they’ve evaluated to be of the highest standards.

This is a wonderful cafe to visit for breakfast or brunch. There’s plenty of indoor and outdoor seating. They serve an assortment of bakery treats and light meals. I enjoyed a fantastic coffee and a Spanish tortilla. And the town of West Stockbridge is adorable.

While Six Depot is my favorite coffeeshop in the Berkshires, there are plenty more you can visit! (I tried to visit THEM ALL! And got to almost all of them!) My second-favorite is Tunnel City Coffee , which pairs well with a visit to the Clark Institute. (There are a few locations but I recommend their flagship in Williamstown, which is huge, has a giant case full of gorgeous pastries, and has a jovial student crowd.)

Some other places with excellent coffee are Stockbridge Coffee and Tea in Stockbridge, Shots Cafe in Lenox, and Fuel in Great Barrington.

Hilltop Orchards

You might see Hilltop Orchards in Richmond on your Berkshires map — and come here for the apple picking. Or for tasting the local artisanal cider from Jmash Cidery. And let’s not forget the local wine tasting from Furnace Book Winery. There are even hiking trails with great mountain views.

But one item stands out here. CIDER DONUTS.

Holy hell, these cider donuts may be the best cider donuts I HAVE EVER HAD IN MY LIFE. They’re on the small side, almost unfathomably moist, and covered with delicious cinnamon sugar.

I ordered two and somehow ended up with three in my bag. IT WAS NOT ENOUGH. I should have gotten six for $5!

Trust me…if for no other reason, you need to come here for the cider donuts. This is probably one of my top three things to do in the Berkshires. There’s a reason why everyone recommends them!

Bright Ideas Brewing

One of the cool things about MASS MoCA in North Adams is the ecosystem that grew around it — cool new hotels, restaurants, coffeeshops, and bars. And I enjoyed spending an evening at Bright Ideas Brewing !

This brewery features a rotating selection of delicious home-brewed beers — some made with international ingredients. I particularly enjoyed the Northern Lights, made with an unexpected ingredient — taiheke from New Zealand!

I also appreciated that the brewery was around the corner from my hotel, Porches at MASS MoCA, so I could happily imbibe without worrying about driving.

Other craft breweries worth visiting in the Berkshires are Berkshire Brewing Company in South Deerfield, Shire Breu-Hous in Dalton, Big Elm Brewing in Sheffield, and Barrington Brewery and Restaurant in Great Barrington.

Where to Stay in the Berkshires

If you’re looking to stay in the Berkshires, you should decide whether you want to concentrate on the south (Stockbridge, Lenox, Lee, Great Barrington) or north (North Adams, Williamstown, Pittsfield). Technically you can do it all in one trip, as I did.

I chose to try out two nights in the south at the Red Lion Inn in Stockbridge and one night in the north at Porches at MASS MoCA in North Adams. These are two small, independent hotels, the kinds of places I love to stay. Both hotels hosted me on a comped media stay.

As soon as I told my friends I was visiting the Berkshires, several of them told me, “Oh, are you going to the Red Lion?” If anywhere is THE place to stay in the Berkshires, it’s here.

The Red Lion Inn is one of the oldest continuously operating inns in the United States, having been open since 1773. Today, the inn has expanded and covers several buildings within a few blocks — including Maple Glen, the building where I stayed.

The Red Lion is located in downtown Stockbridge, which I think is one of the best places to base in the Berkshires. Not only is it a beautiful town with lots to see and do, it gives you easy access to Lenox, Great Barrington, and nearby small towns; plus, if you want to do Williamsburg and North Adams for the day, this part of the state is less than an hour away.

This was my queen room with a fun mix of colors and patterns.

Lots of seating and a good area for working, if you need to.

I loved the display sculptures in Maple Glen!

My room blended country charm with modern amenities. I appreciated the large size — and that it came with a decent-sized bathtub! The wifi worked well — very important, as Stockbridge is a dead zone for phone signal — and it was nice and quiet at night.

I went to the restaurant one night, which serves classic Yankee cuisine. The restaurant, the pub, and even the front porch feel like a gathering place in Stockbridge, with interesting people passing through.

One tip: don’t bring all your bags when you check in. I did, then I found out I had to schlep them outside and down the street to another building.

Rooms from $148 per night.

Porches at MASS MoCA

North Adams is all about reinvention, and Porches at MASS MoCA is one of the coolest building concepts I’ve seen. The hotel is built from a long strip of 19th century Victorian row houses along the Hoosic River, reconstructed and joined into one long building.

Porches calls itself “whimsical” frequently — and they love the phrase “granny chic.” Personally, I loved it! Such a cool mix of vintage and modern accessories, a vibrant color palette, homey and comforting. It fits North Adams perfectly.

I loved the colors, those lamps, and the divider between rooms.

This is full-on granny chic and I loved it.

This was the inside of one of the Victorian houses — the indoor/outdoor mix kind of reminded me of Vegas, believe it or not.

North Adams makes a good base for visiting the northern part of the Berkshires — towns like Williamstown, Lanesborough, Pittsfield, Florida, and Cheshire. And Porches is right across the street from MASS MoCA — which meant I could enjoy two beers at Bright Ideas Brewing without having to drive!

If you want to hang out at Porches, there are plenty of rocking chairs on the front porches, as well as a pool area in the back.

Rooms from $149 per night.

Overall, these were two great places to stay in the Berkshires, but they were so different! Overall, I loved the location and history of the Red Lion, but I preferred the design and vibe of Porches. If you’re coming to the Berkshires for three nights and don’t mind changing accommodation, why don’t you try both?

See more places to stay in the Berkshires here.

Berkshires Travel Tips

Here are some things you should know before traveling in the Berkshires:

Phone signal is poor in parts of the Berkshires. In fact, the entire town of Stockbridge is a dead zone for phone signal, which shocked me. If you’re using your phone for GPS, as I did, you should load directions while you have access to wifi.

The Berkshires are quiet during the week, especially outside high season. I visited from Monday through Thursday, which I thought would allow me fewer crowds. It sure did — and TONS of places were closed! You should check to make sure your favorite attraction isn’t closed when you’re visiting.

Prices can quickly snowball in the Berkshires. Most museums and historic sites cost around $20. That can quickly add up when you’re doing three or four in a day! It’s best to figure out before you go how much you want to spend and what your biggest priorities are.

Look for combination tickets if you’re hitting up a lot of museums. You can buy a combination ticket to MASS MoCA, the Clark Institute, and the Williams College Museum of Art for $34. Pick it up in any of the three spots.

A lot of coffeeshops in the Berkshires close at 2:00 PM during the week. I found this disappointing, as I love a midafternoon coffeeshop visit when I travel.

Best Time to Visit the Berkshires

Most people say that the best time to visit the Berkshires is either the summer or the fall. The summer because it’s when the most events are on — Tanglewood, Jacob’s Pillow, all the theater performances — and the fall is when you get the best foliage.

Keep in mind that the absolute busiest time in the Berkshires is during summer and fall weekends. You can expect big crowds and high prices with both peaking on the Fourth of July, Labor Day, and Columbus Day.

If you’re looking to experience the best foliage in the Berkshires, time your visit from late September through mid-October. Columbus Day is usually pretty solid for foliage. Though it’s always a smart idea to check an almanac as this can vary from year to year.

I visited the Berkshires in mid-May and it was a surprisingly good time to visit. There were no performances going on, but the weather was absolutely glorious; it was actually much sunnier and warmer than Boston! (That doesn’t always happen, though. May in New England can often be chilly and rainy.)

Winter is a slow and quiet time of year — but this is a great time to visit the Berkshires if you’re looking to ski, snowshoe, or bundle up by the fireplace.

Keep in mind that early spring in New England is “mud season” — and most if not all of April falls into this category. Spring hits later here than many parts of the US.

How to Get to the Berkshires

You need a car in the Berkshires. Can you do the Berkshires without a car? I’m sure someone has, but I really don’t recommend it.

Everything requires driving. Even if you base in a town like Stockbridge, getting to local attractions like the Norman Rockwell Museum, Chesterwood, Naumkeag, and the Berkshire Botanical Gardens requires a 10-minute drive!

Most people drive to the Berkshires. Depending on where you base, it’s about a 2:15-2:45 drive from Boston and a 2:45-3:15 drive from New York City.

If you’re flying to the Berkshires, the closest major airport is in Albany, about a 45-minute drive from Stockbridge.

There are bus and train connections to Pittsfield.

Are the Berkshires worth it?

Yes! Absolutely! I loved my trip to the Berkshires, and my only regret was that I waited so long to visit this wonderful part of my home state.

And to my fellow Bay Staters, New Englanders, and tri-staters — if you haven’t been to the Berkshires yet, maybe it’s time for you to make the trip! Pick a long weekend and start researching. I think you’ll fall in love with this beautiful part of the world.

Western Massachusetts:

• Best Towns in the Berkshires, Massachusetts

Best of Boston:

• What NOT to Do in Boston
• Where to Stay in Boston: Best Neighborhoods & Hotels
• 40+ Fun Things to Do in Boston at Night
• Best Time to Visit Boston
• 24 Interesting Things to Do in Cambridge, Mass.
• 12+ Best Day Trips From Boston
• 21 Best Museums in Boston

Cape Cod & the Islands:

• Which of the Towns of Cape Cod is Best for You?
• 24 Fab Things to Do in Cape Cod
• 22 Fabulous Things to Do in Provincetown, MA
• Which Of The 6 Martha’s Vineyard Towns Is Best For You?
• A Guide to Oak Bluffs, MA — Home of the Gingerbread Houses
• A Guide to Edgartown, MA — Prettiest Martha’s Vineyard Town
• A Guide to Vineyard Haven, MA — Authentic Town on Martha’s Vineyard
• 24 Cool Things to Do in Lenox, MA
• 12 Fun Things to Do in Stockbridge, MA

North Shore:

• 27 Fun Things to Do in Rockport, Mass.
• 25 Spooky, Haunted Things to Do in Salem, Mass.

Thanks to the Red Lion Inn and Porches at MASS MoCA for hosting me for three nights altogether in the Berkshires. I also received comped admission to the Norman Rockwell Museum, Naumkeag, Chesterwood, The Mount, Berkshire Botanical Garden, Ventfort Hall, Hancock Shaker Village, Clark Institute, MASS MoCA, the Berkshire Museum, and Arrowhead. All opinions, as always, are my own.

1 thought on “33 Best Things to Do in the Berkshires”

Hi there, I’ve been to all 50 states and last year for the first time we did the Poconos in PA and loved it. The Berkshires are on my list so glad to read it not’s just for the rich (think real housewives lol) and very excited to see there are waterfalls. I can’t wait to visit this area. Nikki

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Home » Travel Guides » United Kingdom » England » 15 Best Places to Visit in Berkshire (England)

15 Best Places to Visit in Berkshire (England)

One of the Home Counties, Berkshire’s bucolic rural scenery coupled with being close to London makes it a place where most people will pay handsomely for property.

The county can be extremely fancy, and has been home to royalty since the early 1100s when Windsor Castle was built.

The presence of royalty can be felt in many places, including the distinguished racecourse at Ascot.

And as we work our way through Berkshire you’ll see how much the county’s waterways contribute to its charm.

The Thames meanders west to east, broadening as it goes and nourishing verdant water meadows beside the towns and villages.

The Kennet and Avon Canal was also an important shipping route from the West Country to London, and is now navigated by holidaymakers on barges.

Lets explore the best places to visit in Berkshire :

Two of the most visited attractions in the country are in this regal town on the Thames.

Windsor Castle hardly needs introduction: Since the reign of Henry I in the early 12th century this has been residence for the royal family, which makes it the oldest occupied royal palace in Europe.

You could easily get lost in the 5,000-hectare Great Park, while you can spend a few hours idling around the town, seeing sights like Christopher Wren’s 17th-century Guildhall.

And then for little guys there’s LEGOLAND Windsor, which in 2016 became the UK’s favourite theme park and promises a day of LEGO-themed amusements and rides for kids up to 12.

A well-preserved historic town, the centre of Newbury makes for an agreeable walk, and the grassy tow paths on the Kennet and Avon Canal are wonderfully serene . Newbury Racecourse hosts the Lockinge Stakes in May, one of the most valuable races on the calendar.

The stately home, Highclere Castle is majestic, and is in a sweeping 2,000-hectare estate.

It needs to be part of your plans if you’re a fan of Downton Abbey, as one glance will tell you that this was where the TV show was filmed.

The house is newer than it looks, from the 1800s, and has a “Jacobethan” design inspired by the 16th and 17th-century palaces.

Ramble on the downs in the surrounding country parks, and get to Donnington Castle, where an 18-month siege took place in the English Civil War.

Without knowing about its culinary pedigree, Bray would seem like any other well-to-do and charming village in the South of England.

There are almshouses from the early 1600s and the handsome Church of St Michael, which was constructed in the 1290s and has a lot of riveting medieval artefacts within, including a monumental brass on the tomb of Sir John Foxley.

But Bray’s modern reputation comes from its restaurants, as two of the four three Michelin-starred establishments are in the this village.

The older of the two is the Waterside Inn, founded by the Roux brothers in 1972, while Heston Blumenthal’s Fat Duck has won acclaim for its molecular gastronomy since opening in 1995.

Although it doesn’t get a lot of credit for its looks, Reading is a large and thriving urban centre with a high-ranking university and all the shopping you can handle.

Being close to London it became a manufacturing town in the 1800s and was endowed with perfect transport links, where the Kennet and Avon Canal joins the Thames.

You’re also just a couple of miles east of the North Wessex Downs, with their lush green hills and crystal-clear chalk streams should you crave the countryside.

In the town, poke around the ruins of Reading Abbey and drop by at attractions like the Museum of Zoology, Museum of Berkshire Aviation and the Museum of English Rural Life.

5. Wokingham

In Tudor times Wokingham was a centre for silk spinning, and small hints of this industry remain.

Have a stroll along Rose Street, where the half-timbered houses with taller bottom floors would have contained looms.

The Victorian Gothic revival town hall in the middle of Market Place is still at the heart of the community, with a stylish cafe in its courtyard, and the historic buildings around it house a mix of locally-owned shops and high street brands.

There are a few walks you can begin right in the town, like the path up to Fichampstead Ridges, clad with woodland and heather.

6. Hungerford

Close to Wiltshire in the North Wessex Downs, Hungerford is a little way from Walbury Hill, which at almost 300 metres is the highest point in the Southeast.

The Kennet and Avon Canal curves past the northern side of the town and in the 19th century transported coal and stone quarried from Somerset up towards Reading on the Thames.

Hungerford Wharf is achingly pretty and a wonderful place to see the narrowboats gliding up and down the canal on a sunny day.

Cross the bridge in the town for a taste of southern rural England on the high street, with lots of 17th and 18th century properties, including the Hungerford Arcade, an antiques centre with more than 100 dealers under one roof.

Opposite Windsor on the north bank of the Thames is the town of Eton, synonymous with Eton College.

This is the most famous and prestigious of all of England’s Public Schools, founded by Henry VI and with 19 former British Prime Ministers among its alumni.

If you’re in any doubt about how posh this place is the school has its own Natural History Museum, open on Sundays, but you can arrange a visit at other times.

Eton’s high street has rows of historic brick and half-timbered buildings housing upmarket shops like a delicatessen and antique bookshops, and to stretch your legs there’s lovely green space at the Brocas and South Meadow next to the Thames.

8. Pangbourne

Anybody who recalls the children’s book the “Wind in the Willows” will be interested to learn that its author Kenneth Grahame retired in Pangbourne in the 1920s.

The village is full of handsome old houses with one-off shops, and made all the more picturesque by the Thames.

On the banks are large green water meadows owned by Pangbourne and where the village fete takes place every June.

For the rest of the summer they’re a dreamy spot for a picnic in the shade of the willow trees.

If you’re travelling with little ones they’ll have a fun time at Beale Park, a gentle attraction with farm animals and more exotic species like meerkats, lemurs and mongooses.

The three villages that make up the town of Ascot are very well-heeled and are mostly geared towards Ascot Racecourse, which is surely the most prestigious in the country.

So for visitors who show up for the 26 days of racing each year in need of accommodation there are plenty of hotels and restaurants.

The course has close links to the royal family, having been established by Queen Anne in 1711 and  is situated just a few miles from Windsor.

Royal Ascot Week in June remains wildly popular, packing in 300,000 spectators and attended without fail by Queen Elizabeth.

Since the 18th century this event has been a mainstay of the “London Season” for the country’s social elite.

10. Streatley

At an ancient crossing on the Thames, Streatley is a stunning village right next to the larger town of Goring, across the county line in South Oxfordshire.

The landscape is one of steep wooded hills that are outcrops of the Chiltern Range on the eastern cusp of the North Wessex downs.

A lot of the surrounding countryside is owned by the National Trust so you’re free to walk up and admire of the views of the river and village, while Ridgeway National Trail crosses the Thames at Goring and Streatley on its way east.

In this very upmarket spot you have a fine selection of pubs and restaurants, and there’s also a golf club open to visitors and running since 1895.

11. Maidenhead

The large town of Maidenhead is just across the river from  Buckinghamshire, and links to the neighbouring village of Taplow via the Maidenhead Bridge.

This structure gives us one of the loveliest sights in the town, and was built in the 1770s with seven arches and wrought iron lanterns.

You could walk a small stretch of the Thames Path up to Boulter’s Lock, which is also from the 1700s and is a wonderful spot to sit and ponder the river and its weir, or watch the barges go by.

And between Boulter’s Lock and Bray Lock is the Maidenhead Railway Bridge, designed by the revered Isambard Kingdom Brunel in 1839. The Maidenhead Heritage Centre can clue you in on the town’s connection to the Air Transport Auxiliary, which was based near the town in the Second World War and helped move vital RAF machinery around the country.

12. Cookham

One of Britain’s most acclaimed 20th-century painters, Stanley Spencer was born in this Thameside village where he also spent a great deal of his life.

Now in the Wesleyan Chapel that he attended when he was growing up there’s a museum with more than 100 of Spencer’s paintings and drawings.

Give yourself time to see a bit more of the village and its common, where there a blend of timber-framed houses and adorable cottages with flint walls.

You’ll be looking at some of the most expensive property per square-metre in England, in what is often described as the richest village in the country.

13. Kintbury

In the green rolling hills of the North Wessex Downs, the small waterside village of Kintbury polls among the best villages in the country.

You won’t be blown away by any amazing sights, but can see rural England at its primmest in one of the most coveted addresses around.

On the high street the older part of the village looks much as it did a century ago, with delightful brick cottages and a rustic medieval church.

Stop at the 18th-century Dundas Arms next to the Kennet and Avon Canal for a pub lunch with a gentrified twist.

14. Sulhamstead

Another understated pick for an excursion, Sulhamstead does have one high-profile visitor attraction in the Thames Valley Police Museum.

You can just show up on a Wednesday, and on other days of the week you’ll need to phone ahead.

But if you’re fascinated by one of 20th century Britain’s most notorious heist’s, this museum in a beautiful neoclassical mansion has artefacts relating to the Great Train Robbery in 1963. On the Kennet and Avon Canal is the endearing Tyle Mill, which was originally for flour and later became a sawmill, loading and shipping timber with the help of the wharf.

Just up from Eton and Windsor, this workmanlike town doesn’t have the same reputation for history and architecture; rather it’s a place of business and industry that complements the more genteel places nearby.

The bricks for Eton College were baked in Slough, and the Industrial Estate remains a hive of activity and a base for international companies like LEGO and McAfee.

People head to the centre for the Observatory Shopping Mall, which has 120 stores, and Slough is right by the Colne Valley Regional Park, a large, mostly undeveloped space that acts as a green buffer around the M25.

15 Best Places to Visit in Berkshire (England):

• Sulhamstead

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Things To Do in Berkshire

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With so many places to visit in Berkshire, you can easily forget you're right on London’s doorstep. Just 45 minutes by train from London, you'll discover a wealth of towns, villages and countryside to explore, making this county the perfect antidote to UK city life.  A county with unique connections to the British Royal Family, where you will find the River Thames meandering along its northern edge and beautiful parks and gardens ablaze with colour. 

The North Wessex Downs (AONB) to the west of the county, a rich mosaic of chalk habitat, woodland, pastures and common land and the world famous historic town of Windsor to the east.  You'll find a year round events calendar, along with vibrant riverside towns of Reading and Maidenhead, the famous college of Eton and the place where the historic Magna Carta was signed.  Today this romantic county offers the perfect escape from the everyday, combining royal heritage, a slice of luxury with the great outdoors.  To get the most out of your stay, start planning your days out in Berkshire here.

Visit Berkshire

Windsor , Berkshire, the weekend home of the British Royal family, home to the iconic Windsor Castle, the world famous long walk and the beautiful Windsor Great Park.  With history and heritage at every turn, beautiful parks and gardens, riverside walks and great shopping, this beautiful historic town makes for a great South East short break destination.

Berkshire is the birthplace of the Duchess of Cambridge, Kate Middleton, raised in the quaint village of Buckleberry where her parents’ home is still located today. It was in the village of Pangbourne in Berkshire where she spent her school days at St Andrew’s School. Situated on the River Thames, Pangbourne has been cited as the inspiration of many famous authors’ novels including Kenneth Grahame and Jerome K. Jerome.  Full of character, Pangbourne is a great place to visit.

Vibrant Reading , Berkshire, a modern destination with a medieval history, packed full of in or on the water activities, adrenaline fuled attractions, rich history and great places to stay.  Located on the River Thames it is home to the 900 year old Reading Abbey ruins, the Reading Festival, and the departure point for modern pilgrims and walkers retracing the steps of medieval pilgrims along St James’ Way to Southampton.  

Berkshire is also home to many other picturesque towns and villages such as  Newbury , Hungerford ,  Ascot , Hurley, Cookham, Bray, Littlewick Green, and Waltham St Lawrence. Find out more about towns and villages in the county with our interactive map of Berkshire .

Things to do in Berkshire this weekend

Many of Berkshire's tourist attractions are open all year round so find the best days out in Berkshire with activities listings each showing a map and opening times for your convenience. Or why not browse our Berkshire events guide to find out what's on this week.

Top 10 things to do in Berkshire

For things to do in Reading, Newbury, Maidenhead , Bracknell and other Berkshire towns, browse our pick of the best attractions below or find a more comprehensive list of what to do and places to visit at the bottom of the page.

• The Savill Garden , Windsor
• Windsor Castle and the Changing of the Guard , Windsor
• Thames Rivercruise Boat Trips , Caversham
• Kennet Horse Boat Company , Hungerford
• Kris Cruises , Slough
• Newbury Racecourse , Newbury
• Norden Farm Centre for the Arts , Maidenhead
• The Coconut Tree , Reading
• Ascot Racecourse , Windsor
• Museum of Rural Life , Reading

List of things to do & places to visit for days out in Berkshire

For more about Berkshire, including ideas on days out, where to stay and things to do in Berkshire, browse through the below selection of attractions and towns and villages that collectively make Berkshire such a memorable destination to visit. Use the 'map view' button to find something near you.

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Streatley-on-Thames

The village of Streatley-on-Thames stands on the opposite side of the River Thames to Goring; Oxfordshire on one side and West Berkshire on the other, linked by a bridge which was built in 1923

Bracknell is a town and civil parish in the Borough of Bracknell Forest in Berkshire.

Windsor & Maidenhead Boat Company

Here at the Windsor & Maidenhead Boat Company, we like to make your day out one to remember. We operate a beautiful vessel called the Georgian, which is more like a floating restaurant rather than a boat that you might expect. We offer four types of…

In the days when the River Thames meandered through a wide flood plain, and in the absence of bridges, Clewer became well known for its ford as this was the only place to cross the river for several miles. It was used by soldiers, traders and…

What's happening in Newbury?

Set along the banks of the River Kennet and the Kennet and Avon Canal, Newbury has a fresh, rural atmosphere combined with great shopping facilities and new attractions.

White Waltham

Although an area of great antiquity, where Roman remains have been found, White Waltham has seen more change during the past 60 years than all its previous history. This is due to the establishment of White Waltham Airfield during World War II and…

Wokingham is a market town and civil parish in Berkshire It is about 7 miles east-southeast of Reading and 4 miles west of Bracknell.

The charming market town of Hungerford can be found in the West of Berkshire. Find a map, details about the town, tourist information and things to do.

Waltham St Lawrence

One of the most westerly parishes in the borough, Waltham St Lawrence includes the hamlets of West End and Shurlock Row and contains many fine examples of domestic architecture.

The village is centred on its cattle pound, around which are many…

Changing the Guard

Sightseeing

The Changing of the Guard is one of the highlights of a visit to Windsor. A band usually accompanies the Guards, although this is subject to weather conditions.

The Guards can be watched as they march up the High Street and into the Castle, but…

Sonning, occasionally called Sonning-on-Thames is a village and civil parish in the Borough of Wokingham in the English county of Berkshire, a few miles east of Reading.

Coral Reef Bracknell's Water World

Adventure Park / Playground

Find out why this has become one of Berkshire's most popular attractions with with 3 giant water slides, pirate ship, erupting volcano and water rapids.

Caprice at Crowne Plaza Reading East

Winnersh Triangle, WOKINGHAM

Sat within the new, fully refurbished, 4 Silver Star Crowne Plaza Reading East, the 2 AA Rosette Caprice Restaurant and Monty’s Lounge & Bar with superb terrace serves modern British & authentic Indian dishes as well as Splendid Afternoon Teas…

Slough is a town in Berkshire, England, about 20 miles west of central London.

The Coconut Tree

Vegan Friendly

Experience an explosion of flavours in our vegetables, meats & fish along with sweet & fiery Cocktails… a naturally abundant vegan & vegetarian cuisine. INTRO YOUR CREW’ TO SRI LANKAN SREET FOOD 50% off every Mon-Wed: INTRO YOUR CREW *eat in only.…

Nestling along the River Thames, Pangbourne is subject of much literary inspiration. A charming place, undeserving of being labelled Pongbourne by author DH Lawrence.

Wellington Country Park

Country / Royal Park

Riseley, Reading

Wellington Country Park, ‘The Biggest Outdoor play in Berkshire’, was established in 1974 by the Eighth Duke and Duchess of Wellington. Set in 350 acres of beautiful parklands off the A33 between Basingstoke and Reading, Wellington Country Park…

Newbury Racecourse

Sports Ground

Newbury Racecourse is one of the most famous and prestigious horseracing venues in the UK, providing world class racing all-year-round and excellent facilities for conferences and events.

Cobbs Farm Shop

Cobbs was founded out of a passion for supplying quality food with provenance to our customers as well as providing a platform to the immense volume of artisanal producers on our doorstep. You will find a fantastic farm shop, delicatessen, butchery,…

Holme Grange Craft Village

Craft Centre

We offer a wide range of goods and services and a fabulous tea shop in a historic barn opening onto a beautiful enclosed courtyard where you can sit and relax while you enjoy your refreshment.

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Places To Visit In the Berkshires, Where Culture Meets Nature

Planning a road trip in the Berkshires, nestled in bucolic western Massachusetts? This is the ultimate guide to all the best places to visit in the Berkshires. It covers the must visit towns, cities, parks, museums, and landmarks.

The Berkshires are a lovely area, almost ripped from paintings at a museum. The Berkshires are dusted with magic, and the perfect place for a New England road trip .

The region evokes an earlier America, with houses and architecture straight from a Norman Rockwell painting.

The Berkshires is a laid back region, quietly unbuttoned without the glitz or cocktail party circuit. The area was made famous by literary figures escaping the city to their turn of the century castle-cottages, set under solitary starry nights.

The Berkshires are full of winding roads with undulating meadows, deep green ellipses of hills, organic farms, and trees ablaze in autumn.

But it’s definitely not just for nature lovers and leaf peepers. The Berkshires are a unique confluence of nature, historic landmarks, cultural gems, and vaunted museums.

In fact, the Berkshires are New England’s premiere summer region for culture-driven travel and road trips. Wherever you go, you’ll be confronted with the choice: art or the great outdoors?

Despite its rural setting, the Berkshires also have a hot foodie scene, with a hip farm to table vibe. In the Berkshires, restaurant owners source food locally from innovative farmers, grow their own herbs and micro-greens, and raise hens.

How Long Should You Spend in the Berkshires?

It depends. You could spend a busy weekend or a laid back week on a road trip through the Berkshires region. Each new mile yields new discoveries. If you’re coming from Boston or New York City, budget 3 hours of driving each way.

If you’re embarking on a weekend getaway, use my list of must see destinations and towns to pick and choose the places that most appeal to you in the Berkshires.

The Berkshires are small enough that you can base in one part and explore the whole region. If you want one base, choose Lenox or Stockbridge.

They’re the prettiest towns, looking exactly as you’d imagine a classic New England village. Both have amazing cultural, culinary, and outdoor options. They’re centrally located and within easy striking distance of the other must see sites in the Berkshires.

If you want two bases to explore the region in depth, pick North Adams in the north and Stockbridge in the south.

When Should You Go To the Berkshires?

The Berkshires are evolving into a year round destination. Summer is the busiest time in the Berkshires, when people are looking to ditch the bustling city for quieter climes.

If you’re looking to attend concerts, shows, and events, aim for summer. Be sure to book festival and theater tickets in advance.

Fall is gorgeous, but also quite busy. The brilliant foliage and pleasant weather also make fall an idea time to take a fall foliage road trip in New England . In the Berkshires, the foliage typically reaches its peak in mid October.

How To Get To the Berkshires

You really need a car to visit the Berkshires. Everything requires driving. Even if you base in a town like Stockbridge, you need to drive to the local attractions.

Most people drive to the Berkshires. Depending on where you base, it’s about a 2:15-2:45 drive from Boston and a 2:45-3:15 drive from New York City.

If you’re flying to the Berkshires, the closest major airport is in Albany, about a 45 minute drive from Stockbridge. There are also bus and train connections to Pittsfield.

Places To Visit In The Berkshires

How best to experience the Berkshires’ arts and eats ethos? Here are all the best places to visit in the Berkshires — sites, attractions, and most beautiful towns.

I’ve put them in the likely order you’d visit them on a Berkshires road trip, along with tips on what to see, do, eat, and where to stay in the Berkshires. And, of course, where to get your cultural fix.

Let’s go sniff the mountain air, at least virtually.

1. Great Barrington

For some of the best fall foliage scenery in the Berkshires, take Route 7 and 8 from Great Barrington to North Adams (1:10 hours without stops).

You’ll go past storybook farms, wooden barns, and stone walls. And through the cute towns of Stockbridge, Lee, Lennox, and Pittsfield.

Great Barrington is a town for foodies and antique hunters. It has a fashionable shopping district and excellent restaurants.

Stop in at the the Berkshire Art Gallery, which features a wide range of 19th and 20th century American and European paintings. If you’re a pottery enthusiast, head 12 minutes south of Great Barrington to the nearby Sheffield Pottery.

In terms of outdoor recreation, You can head to Blueberry Hill to pick wild blueberries. For great views and relatively easy hiking, head to Monument Mountain .

Monument Mountain Summit is a 3.8 mile lightly trafficked out and back trail. It features wildflowers, but no views. If you want a vista, you need to sidetrack to Squaw Peak.

Monument Mountain is famously the setting for a double date between authors Herman Melville and Nathaniel Hawthorne. They met and hiked up the mountain. Legend holds that they were caught in a rainstorm during which Hawthorne convinced Melville to write Moby Dick .

• Where to stay in Great Barrington : The Barrington, Thornewood Inn, Granville House
• Where to eat in Great Barrington : Prairie Whale, Rubi’s Cafe, Cheesemongers & Grocers, Meat Market, Bizen, John Andrews, cafeADAM

2. Bash Bish Falls

From Great Barrington detour 12 minutes to Bash Bish Falls in Egremont. Bash Bish is the largest single drop waterfall in Massachusetts and a must see in the Berkshires. Water is sliced in two by a massive boulder creating a picture perfect double waterfall .

At 80 foot high, it’s not Niagara size. But it’s still pretty. A steep 20 minute trail leads from the parking lot.

Bash Bish is on the Massachusetts-New York border. If you want a less challenging hike, drive 1 mile west to the New York side parking lot.

Picturesque Bash Bish Falls has been a popular Berkshires tourist stop since the mid 19th century. When you come upon the falls, you’ll feel as though you’ve discovered a secret, woodland spot. But, be forewarned, there will be many other waterfall pilgrims at this uber popular hiking spot.

3. Stockbridge

Settled in 1734 by British missionaries, Stockbridge may be my favorite adorable small town in the Berkshires. It’s blessed with simple charm and a fabulous line up of cultural attractions.

Three of the greatest American artists and authors called Stockbridge their home — Edna St. Vincent Millay, Herman Melville, and Norman Rockwell. James Taylor sang about the town in Sweet Baby James .

One of America’s greatest treasures is the Norman Rockwell Museum . Rockwell was one of the greatest artists and illustrators in American history. Stockbridge was Rockwell’s long time residence and what he called his “best studio yet.”

His titular museum is home to a year round series of rotating exhibitions of Rockwell’s art and Saturday Evening Post magazine covers. There are 570 Rockwell illustrations, including the famous Triple Self Portrait and Going and Coming .

A permanent exhibit is the quartet called the Four Freedoms , which will seem comfortingly familiar. The most famous of these gems is Freedom From Wont , depicting a family gathering at Thanksgiving.

Rockwell’s studio was painstakingly moved intact to the grounds as well. There, you’ll learn about his creative process.

At Christmas, Stockbridge charms visitors with a re-staging of Rockwell’s painting from McCall’s Magazine, Stockbridge Main Street at Christmas .

You can also visit Chesterwood , the home Daniel Chester House. It’s the 1920s Colonial Revival house, complete with soaring studio, of the legendary sculptor and landscape architect.

Chester created the statue of President Lincoln seated in the Lincoln Memorial in Washington D.C., and you’ll see plaster models in the museum.

The summer estate is beautiful, but it’s Chesterwood’s hiking trails that are acclaimed. Some say that Chester “sculpted the landscape as well.”

After a stroll through the formal gardens, take the easy Woodland Walk carving through the wilder woods. Or, for more of a challenge, try the Ledges Trail with a steep climb to a viewpoint.

Apart from visual arts and historic, the Berkshire Theater Group provides performing arts entertainment. The IS 183 Gallery has a stash of regional and national art works.

Every summer, Stockbridge (along with the town of Lenox) hosts the Tanglewood Music Festival, a series of concerts across all musical disciplines.

Stockbridge is also home to one of the Berkshires Gilded Age “cottages,” Naumkeag . You can tour this quirky 44 room mansion designed by Stanford White, famed starchitect of the time. It boasts original furnishings, rooms full of angles and curves, and captivating gardens.

To get outside in Stockbridge, drive to the end of Park Street and walk through a stone portal into another world, Ice Glen.

You’ll find romantic rugged landscapes, giant tree roots, and massive Ice Age boulders. You’ll need to be fit and agile to hike either the one mile out and back or two mile loop trail.

• Where to stay in Stockbridge : Once Upon a Table, Truc Orient Express
• Where to eat in Stockbridge : The Red Lion Inn, The Inn at Stockbridge

Lenox is a pretty must visit place in the Berkshires. It’s full of art galleries and upscale boutiques housed in historic buildings. It’s probably the priciest place in the Berkshires.

You’ll find the classic Berkshires experience and some of the region’s most iconic properties — Blantyre, Wheatleigh, Canyon Ranch, and The Mount. At one point, there were so many lavish summer homes that Lenox was known as “the inland Newport.”

In 1902, Edith Wharton, the first woman to win the Pulitzer Prize in Literature, built The Mount in Lenox. It was a stately country retreat for the literary lioness and her then-husband, modeled after European manses but lacking their excesses.

No gaudy entries or vulgar grand staircases for the “Lady of Lenox,” who happily lived a corset free life and wrote Ethan Frome and The House of Mirth there. She did most of her writing in her third floor bedroom — in bed!

The Mount has been beautifully restored to its appearance during Wharton’s tenure. The exterior is a striking white stucco, with clusters of gables and white chimneys and a roof capped with a balustrade and a cupola.

Wharton had a lot of style. You might find yourself longing for her furnishings.

Wharton had a pale pink dining room with fuchsia and gold cutlery. The house is a remarkable portrait of how the wealthy lived during this time period. It makes you think about how idyllic surroundings can inspire you as an artist.

The Mount is home to a summer lecture series, weekly bird walks, concerts, theater performances, and outdoor sculpture exhibits. Edith Wharton’s library has been returned to the house, with 22 first editions of her work.

If you want a drink or light meal, head to The Mount’s Terrace Cafe. Then wander in the beautifully landscaped gardens. On Friday Night Fright in September and October, a 2 hour ghost tour traverses the haunted parts of The Mount.

If you like modern art, the Frelinghuysen Morris House & Studio is also worth a Lenox look.

It’s a modernist home exhibiting the works of Suzy Frelinghuysen and George L.K. Morris. It also boasts works by their cubist contemporaries — Pablo Picasso, Juan Gris, and Georges Braque.

For a long walk in the woods, head to nearby Olivia’s Overlook at the center of the Yokun Ridge. The overlook is also the trailhead for several trails varying in length. You’ll have great views, see wildflowers, and the pretty Monks Pond.

• Where to stay in Lenox : Birchwood Inn, Blantyre, Brook farm Inn, Applegate Inn, Devonfield Inn, Gateways Inn and Restaurant
• Where to eat in Lenox : Nudel, Wheatleigh, Bistro Zinc, Alpamayo, Cafe Lucia

5. Pittsfield

While not as quaint as the other Berkshires towns, there are still some things to do that are worth a stop in Pittsfield on your Berkshires itinerary.

The Berkshire Museum has undergone a major renovation. It showcases everything from a stegosaurus to Alexander Calder mobiles.

If you’re a Henry Melville fan, stop in at his small yellow house, Arrowhead . The author lived in this converted warehouse during his most productive years.

He wrote Moby Dick in his second floor study. Melville built his porch on the “wrong” side of the house to better view of Mt. Greylock.

For outdoor fun, 10 minutes down the road is Ashuwillticook Rail Trail. Smack in the middle of two mountains, the 11mile trail is paved for biking, hiking, or cross country skiing.

5 miles southwest of Pittsfield is Hancock Shaker Village , a living slice of American history. It’s a restoration of a religious community that flourished in the 1800s.

The adherents exhibited shaking motions while listening to sermons. You can tour the buildings, including a group dwelling house and stone barn, and watch craftsman at work.

• Where to stay in Pittsfield : Overnight at the excellent choices in Lenox instead
• Where to eat in Pittsfield : Elizabeth’s, Enso Asian Bistro, Mission Bar and Tapas

6. North Adams

30 miles further north lies the quaint town of North Adams. It’s a former manufacturing hub reinvented as a funky cutting edge art town. North Adams is known as “The Town of Steeples and Peaks,” for the spires of its many churches. Come for the art, and stay for the scenery.

Visting North Adams is now one of the best things to do in the Berkshires. Its downtown is filled with art galleries, artists studios, and cute shops. Its pride and joy is Porches Inn, an eye catching row of distinctive multi-colored Victorians.

After meandering the downtown, head straight to the utterly fabulous Massachusetts Museum of Contemporary Art (“MASS MoCA”). Opened in 1999, MoCA is one of the region’s foremost cultural institutions.

MOCA has an emphasis on international contemporary art. The airy industrial campus was expanded in 2017 with new modern buildings by Tadao Ando.

Works are spread out over 250,000 feet in 19 galleries in a renovated 19th century factory, making it the largest contemporary art museum in the US. MoCA is home to exciting works by Louise Bourgeois and Robert Rauschenberg.

Entire walls are decorated by Sol LeWitt. The museum also has a permanent collection with works by the likes of Manet, Constable, Bonnard, Delacroix, Ingres, and Sargent.

In the adjacent town of Adams is the Susan B. Anthony Birthplace Museum . This museum is dedicated to a woman who played a pivotal role in the suffragette movement. There’s a beautiful collection of postcards commemorating the suffrage, abolition, and temperance movements.

In nearby Natural Bridge State Park, you can view the only natural white marble arch in North America. It was carved as a result of glacial melt over 13,000 years ago. A bridge spans Hudson Brook and twists through a 60 foot gorge.

You can also hike the Cascade Trail . The 1.2 mile trail follows Notch Brook up to a cascading waterfall (photo above). It’s an easy one hour or so trail, with one riverbank crossing.

• Where to stay in North Adams : Porches Inn, Topia Inn, Tourists
• Where to eat in North Adams : Gramercy Bistro, Grazie, Public Eat and Drink

7. Williamstown

Just next door to North Adams is the college town of Williamstown, home to Williams College. Williams College is one of the “Little Ivies,” known for its ivy covered buildings, Gothic chapel, and beautiful architecture. It’s one of the best places to visit in the Berkshires.

Williamstown is also home to the Clark Art Institute , a must visit in the Berkshires. It’s one of the United State’s best museums, focusing on historic European and American art.

The amazing museum has been fully renovated and expanded in a mix of architectural styles.

The museum is home to some beautiful works by John Singer Sargent and Winslow Homer and a world class collection of French Impressionist paintings (30 Renoir paintings!)

The Clark Institute is located on a 140 acre compound. It has well marked (and free) hiking trails for year round exploration.

The well manicured paths wind through woods, cresting at the top of Stone Hill. From there, you’ll have a beautiful panoramic views of Williamstown and Vermont’s Green Mountains.

At the Williams College Museum of Art you’ll find modern and contemporary art to admire.

If you’re visiting in the summer months, you can attend the Williamstown Theatre Festival, a 2002 Tony award winner for outstanding regional theater. Williams College offers concerts, recitals, and theatrical productions.

If you didn’t hike at the Clark Institute, try Pine Cobble Trail. The 3.2 mile trail is a steadily ascending climb to the 1,894 foot summit. From the top, you’ll have beautiful views of Williamstown and North Adams.

• Where to stay in Williamstown : Orchards Hotel, River Bend Farm, House at Sweet Brook Farm
• Where to eat in Williamstown : A Frame Bakery, Coyote Flaco, Mezze Bistro & Bar, ‘6 House Pub

8. Mt. Greylock State Reservation

Head back to Notch Road and continue your descent from Williamstown. The road leads to Mt. Greylock State Reservation , one of the best places to visit in the Berkshires.

Its centerpiece is a 3,491 foot peak. You can drive up to the summit for Massachusetts’ highest viewing point, which features views of 5 states on a good day.

There are plenty of marked hiking trails at Mt. Greylock as well, many starting from the parking lot at the mountain’s base. The trails range from easy to aggressive. Click here for the online trail map.

At the top, there’s a War Tower Memorial for WWII veterans, a panoramic view, and Bascom Lodge where you can eat lunch.

dmission to Mount Greylock State Reservation is free. But you’ll have to pay for parking.

• Where to stay in Mt. Greylock : Bascom Lodge
• Where to eat near Mt. Greylock : Bascom Lodge, Eat on North, Powder Hounds Restaurant

9. Lanesborough | Lakeview Orchard | Cheshire

Then descend back down, exit the park, and take Route 7. Turn left on Summer Street and pull into the small town of Lanesborough, where you’ll see pastures and horse farms.

A slight detour off Summer Street takes you to Lakeview Orchard . There, you can pick your own bushel of apples and sip on apple cider. You can also buy pies or grab a sandwich here. The orchard is renowned for its apple cider donuts.

If you have kids, stop in at Whitney’s Farm Market in Cheshire. In the fall, there’s a corn maze, pumpkin picking, and hayrides. The farm also has a large market with baked goods and a deli.

If you want to some adventure, head to Ramblewild . It’s one of the largest tree to tree aerial adventure parks in the northeast US. You can zipline, climb, and swing through 11 acres of forest.

• Where to stay in Lanesborough : There are better lodging options in Williamstown. Otherwise, try the Harbor House Inn in Cheshire.
• Where to eat in Lanesborough : Old Forge Restaurant

10. Berkshire Festivals

The Berkshires usually have a a packed festival calendar. They celebrate gifted artisans, agricultural harvests, and food | music | art. Here are some of the most popular festivals in the summer and fall seasons:

Tanglewood Music Festival — the 200 acre summer home of the Boston Symphony Orchestra, hosting concerts by world famous musicians in its 200 acre spread

Jacob’s Pillow Dance Festival — showcasing world renowned performers of ballet, modern, and international dance

Shakespeare & Company — the annual repertory season is held in the evenings at The Mount

FreshGrass Festival — a bluegrass festival held at MoCA in North Adams

Berkshires Botanical Garden Harvest Festival — one of the most popular fall festivals in Stockbridge celebrating the harvest and crafts

Lenox Apple Squeeze — street festival celebrating the apple harvest in Lenox

I hope you’ve enjoyed my guide to the best places to visit in the Berkshires. If you’d like to take other US road trips or need some US destination inspiration, I have other guides you may enjoy:

• 10 day Road Trip in New Hampshire
• 10 Day Road Trip for Coastal Maine
• Fall Foliage Road Trip in New England
• 25 Prettiest Towns in New England
• 1 Week Road Trip in Vermont
• 3 Day Itinerary for Boston
• Best Day Trips From Boston
• 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary

If you’d like to visit the Berkshires in Massachusetts, pin it for later.

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Last Updated on March 27, 2023 by Leslie Livingston

How a Black conservative activist arranged Donald Trump's stop at an Atlanta Chick-fil-A

Donald Trump's visit to a Chick-fil-A restaurant location in Atlanta near the campuses of prominent historically black colleges and universities electrified conservative media at a moment when Republicans hope to make inroads with Democrats' most commi...

WASHINGTON -- The scenes of Donald Trump being warmly greeted on Wednesday by a Black audience at a Chick-fil-A restaurant in Atlanta electrified conservative political media at a moment when Republicans hope to make inroads with Democrats’ most committed voting bloc.

Those widely shared moments were days in the making, an alliance between the Trump campaign, local activists, and students at some of the nation’s most iconic historically Black colleges.

Trump and his allies have argued he can win greater Black support due to his messages on the economy and immigration, a notion President Joe Biden's campaign rejects. Some of his outreach to African Americans has played on racial stereotypes — promoting $399 branded sneakers or suggesting that Black people would empathize with his dozens of felony charges — and has offended longtime critics and some potential allies.

But the campaign considered Wednesday's photo opportunity at Chick-fil-A, a stop he made on the way to a fundraiser in Atlanta, a win that produced viral videos shared by his allies and widely discussed by supporters and opponents alike.

“People find it so hard to believe that there are young Black people who would have loved the opportunity to meet Trump,” said Michaelah Montgomery, a conservative activist and founder of Conserve the Culture, which recruits and educates college students and young alumni at Atlanta's historically Black colleges and universities.

Montgomery, a former Georgia Republican Party staffer who regularly coordinates events for HBCU students open to conservative ideas to meet with politicians and activists, said she was notified earlier in the week that Trump would visit Atlanta's Vine City neighborhood during his trip to host a high-dollar fundraiser in the city. She notified a private group chat of students she uses to coordinate events and job opportunities about the president's visit. She received immediate interest in appearing alongside him from around a dozen students.

“Everybody got together at around 9:30 in the morning and walked on over to the Chick-fil-A and then we sat there and waited until the president showed up,” said Montgomery, who can be seen embracing the former president in multiple viral videos. “It’s really disheartening to see that the media makes it seem like we just stumbled into a Chick-fil-A and he bought us milkshakes."

Morehouse and Spelman Colleges are some of the foremost historically Black colleges in the nation, with long legacies of influential Black alumni in politics, business, religion and medicine. Martin Luther King Jr. and Georgia Democratic Sen. Raphael Warnock, who pastors King’s former church, are both Morehouse alumni. Stacey Abrams, the influential Georgia Democrat, attended Spelman. Alongside neighboring Clark Atlanta University and Morris Brown College, the academic collective on Atlanta's West Side has served as a bastion of African American politics and culture since before the Civil Rights movement.

Trump’s overture to students at the iconic Black institutions both underscored his eagerness to show any potential inroads with Black voters as well as the campaign’s strategy of partnering with local conservative groups to marshal a crowd in communities outside the GOP base, a common political tactic with a slight twist.

“The location was beautifully selected and I think it had an incredible impact,” said Bill White, a businessman and longtime friend of the former president who organized the high-dollar luncheon for the Trump campaign in Atlanta’s Buckhead neighborhood the same day. “I just thought the day was a resounding success for him and for the people in Georgia who loved him and wanted to come out and show their support.”

White added that Donald Trump “is very relatable to anyone, really. Atlantans got a chance to see that and show their love back” and he anticipates Trump will make major inroads with Black voters in Atlanta and across the country due to events like his Wednesday visit.

Jasmine Harris, a spokesperson for the Biden campaign, criticized the visit.

“Thinking Black voters relate to Donald Trump because he spent twenty minutes handing out freebies at a fast food restaurant is yet another insult to our intelligence – and perfect example of just how disingenuous Trump’s outreach to Black voters continues to be," Harris said in a statement.

In March, 55 percent of Black Americans said they approved of Biden's handling his job as president while 45 percent disapproved, according to a poll by the AP-NORC Center for Public Research. But a February poll found only a 25 percent favorability rating for Trump among Black Americans.

The visit was not met with fanfare by some on campus or the local community. Montgomery denounced the criticism some students who appeared in the viral videos alongside Trump have received both on campus and online.

“They are claiming that the students made a mockery of their institutions and saying that they are disrespecting their ancestors. It is really, really bad,” said Montgomery.

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Couples Getaway

Posted on February 02, 2019 Written by Lindsey Schmid Updated on February 02, 2019

By Darcie Sosa

It’s the dead of winter. It’s beautiful, but it’s cold, and you’re going just a little bit stir crazy in your house. You and your partner need to get away; in fact, you need a getaway to the Berkshires! Whether this is your first holiday as a couple or a yearly tradition, you can enjoy time together outdoors, exploring our cultural attractions, or simply taking time to reconnect over a delicious meal in a new place.

Enjoy hitting the slopes together? The Berkshires offers both downhill and cross-country skiing . Beautiful cross-country/snowshoe trails can be found at Notchview (a Trustees of Reservations property) as well as at Hilltop Orchards & Furnace Brook Winery , Maple Farms Cross Country Skiing , Cranwell Resort , and Canterbury Farm . Discover our snow-covered Berkshire beauty and enjoy miles of groomed trails. Prefer the thrill of flying down the mountain? The Berkshires is also home to Jiminy Peak Mountain Resort , Bousquet Ski Area , Ski Butternut , as well as two nearby ski areas, Catamount and Berkshire East . All are open for snowboarding and some even offer tubing!

Maybe you’re more into the indoor cultural options ? Even in the cultural off-season, the Berkshires has plenty of those to offer as well. Into contemporary art? The Berkshires is home to several contemporary museums, including Williams College Museum of Art , which hosts a variety of art styles, Berkshire Art Museum , and the largest contemporary art museum in the country, MASS MoCA . Are classic and eclectic art more your style? Museums like the Berkshire Museum , Norman Rockwell Museum , and the Clark Art Institute (which underwent a large renovation five years ago) host beautiful exhibits and have some of the world’s most well-known collections of classic paintings and visual arts.

Once you’ve had your fun, you’ll want to have a fabulous, romantic place to recoup, relax, and recharge. The Berkshires is host to a number of quirky, hip hotels and luxury resorts. Berkshire Inns , which owns and operates several newly-built or renovated hotels, have indoor pools and jacuzzis and offer short and long-term rental options. Courtyard by Marriott Lenox Berkshires also offers bistro dining, a 24-hour gym, an indoor jacuzzi, and an outdoor fire pit. Newly-built or renovated hotels with familiar names, such as the Hampton Inn & Suites and Hilton Garden Inn , offer similar amenities.

Looking for something a bit more quirky? Main Street Hospitality is a Berkshire family organization that owns, operates, develops, and designs unique hotels. Whether you want a boutique experience at the 45-room Hotel on North , (with the delicious Eat on North attached) or Porches Inn at Mass MoCA , or prefer “rustic chic” like the famous and historic Red Lion Inn , (with attached restaurants and pub) you’ll find what you’re looking for. Another beautiful, unique alternative is Tourists Welcome , which since opening, has been written about in Vanity Fair , Vogue , the Boston Globe , and the New York Times .

If you’re looking for a couples luxury getaway, why not stay at one of the Berkshires’ world-renowned luxury resorts, such as Blantyre or Wheatleigh ? Both offer an experience you will not soon forget, and you will be pampered from head to toe. Looking for a wellness getaway? Why not try the world-renowned Canyon Ranch ? Known for its healthy dining, luxury rooms, spa treatments, and other therapeutic wellness amenities. You and your partner will surely leave feeling renewed.

No matter your preferences for things to do or where to stay , you and your honey can find that quick or longer-term stay right here in the Berkshires.

Want more Berkshires? Learn about special happenings , culinary destinations , planning your trip , or even dream about moving to the Berkshires right here.”

Darcie Sosa is a Berkshire marketing/PR professional, who when isn’t working loves being outside hiking with her dogs, going to live music and theatre shows, networking, trying new restaurants and volunteering for local nonprofits. She is an alum of Berkshire Community College, Massachusetts College of Liberal Arts, and the University of Massachusetts, Amherst.

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The 7 best things to stream this weekend, from a shocking true-crime story to a thrilling video-game adaptation

• Check out new shows like "Fallout" and "The Sympathizer" this weekend.
• Movies like "The Greatest Hits" are newly streaming.
• Watch documentaries like "What Jennifer Did" and "Brandy Hellville & The Cult of Fast Fashion."

From dramas to reality TV to true crime, there's something new out for everyone this weekend.

Prime Video's highly anticipated "Fallout" series, based on the beloved video games, dropped its full season on the streamer this week. Entertainment reporter Eammon Jacobs calls it a "masterful adaptation that captures the games' adventure and mystery."

Meanwhile, over on Netflix, "What Jennifer Did" depicts the harrowing true story of a young Canadian woman found guilty of first-degree murder for conspiring to have her strict parents killed.

In the mood for something lighter? There's a new "Bluey" special coming out for parents and kids to enjoy together, or the romantic fantasy "The Greatest Hits" that's perfect for an at-home date night.

Here's a complete rundown of all the best movies, shows, and documentaries to stream this weekend, broken down by what kind of entertainment you're looking for.

'Fallout' is a must-see postapocalyptic drama

Don't be put off by the fact that this guy is missing a nose.

Amazon's new "Fallout" show is worth a watch , whether you're familiar with the original video game series or not. (But if you are a gamer and already blew through the show, I suggest you check out BI's roundup of all the details you missed for a deep-dive into its many Easter eggs.)

From "Westworld" cocreators Jonathan Nolan and Lisa Joy, all eight episodes of the first season are available now.

Streaming on: Prime Video

For a new reality TV fix, watch 'Patti Stanger: The Matchmaker'

If you're an OG "Millionaire Matchmaker" fan, you're in luck: Patti Stanger is back with a new reality show, and she's as unfiltered as ever.

Streaming on: The CW app (or Hulu Live TV )

True crime fans should check out 'What Jennifer Did'

This new true-crime documentary explores the story of Jennifer Pan , a Canadian woman who was convicted of first-degree murder for hiring hitmen to kill her strict Vietnamese immigrant parents when she was 24.

Streaming on: Netflix

Or for a different kind of true story, watch 'Brandy Hellville & The Cult of Fast Fashion'

The HBO Original documentary tracks the rise and fall of Brandy Melville, once a must-have, Instagram-beloved brand for teens.

The fast-fashion company's cult-like following unraveled when allegations of discriminatory work practices — investigated by Business Insider senior correspondent Kate Taylor , who's a featured participant in the doc — came to light.

Streaming on: Max

For something prestige-y, check out 'The Sympathizer'

HBO's new darkly comedic drama is based on the 2015 Pulitzer Prize-winning novel of the same name by Vietnamese-American professor Viet Thanh Nguyen. It follows a half-Vietnamese, half-French communist spy living in America near the end of the Vietnam War.

Robert Downey Jr. serves as an executive producer and also plays multiple antagonists on the show under some heavy makeup and prosthetics . The first episode premieres Sunday.

If you want something to watch with your young kids, stream the new 'Bluey' special

If you're a parent, you know that finding quality children's programming is difficult.

"Bluey" quickly became famous for resonating as much with moms and dads as it does with their children. The beloved, Emmy-winning animated show's first-ever extended special — called "The Sign" and clocking in at a whopping 28 minutes long — hits Disney+ on Sunday.

Streaming on: Disney+

If you want something light and romantic, watch 'The Greatest Hits'

The new movie stars Lucy Boynton as a woman named Harriet grieving her dead boyfriend who discovers she can travel back in time whenever she hears a song from her past. She has to reckon with whether to attempt to change the past or move on with a new love interest in the present. The vibe is very "Time Traveler's Wife."

Streaming on: Hulu

Disclosure: Mathias Döpfner, CEO of Business Insider's parent company, Axel Springer, is a Netflix board member.

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