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The Best Things to Do in the Berkshires, Massachusetts
It’s hard to give just one specific reason to visit the Berkshires because there are so many things to do in the Berkshires of Massachusetts!
This idyllic corner of New England is packed with nature, art, culture, history and amazing food. So, this sounds like your perfect type of vacation, then the Berkshires is the place for you.
The Berkshires were made famous by past American literary legends—like Melville, Thoreau, Hawthorne and Henry Wadsworth Longfellow—who escaped to write there. Celebrities like Meryl Streep, Pete Seeger and Yo-Yo Ma also have houses in the Berkshires.
But the Berkshires isn’t about rubbing elbows with famous people. If you’re craving an escape to one of America’s most nostalgic and charming highland areas, a weekend getaway in the Berkshires is exactly what you need.
TABLE OF CONTENTS:
Where are the Berkshires?
Cultural activities in the Berkshires
Outdoor things to do in the Berkshires
Best fall foliage spots in the Berkshires
Winter activities in Berkshires
Where to eat in the Berkshires
Where to stay in the Berkshires
Berkshires map
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Where are the Berkshires?
The Berkshires are a mountain range region that extends the length of the west of Massachusetts bordered by Vermont to the north, Connecticut to the south and New York to the west. Two major US cities—New York and Boston—are a few hours’ drive away.
Best Things to Do in the Berkshires
Soak up the rich culture of the Berkshires
With such a rich history in arts and literature, the Berkshires in MA offer every culture enthusiast so much to see and do. There are countless museums, galleries, performance centers, outdoor events venues, and historic homes to see. Here are just some of the cultural Berkshires activities:
Mass MOCA (Massachusetts Museum of Contemporary Art)
Image via Shutterstock by T photography
MASS MoCA in North Adams is a must-visit for art lovers. It features some of the most evocative art exhibits by both established and emerging artists in its industrial-style 250,000 square feet of open space. MASS MoCA also boasts a collection of indoor and outdoor performance arts venues.
Their year-round event calendar usually includes over 75 performances from various genres. They include indie-rock, contemporary dance, alternative cabaret, world music dance and outdoor silent films.
Tanglewood
Summer concert at Ozawa Hall, Tanglewood Music Festival, Berkshires Image via Shutterstock by T photography
Tanglewood is an open-air music venue near Lenox that’s a music lover’s dream!
Home to the Boston Symphony Orchestra in the summer months, you can bet that attending an event at Tanglewood is one of the best things to do in the Berkshires summer. Countless big names in classical, pop, jazz and contemporary have performed here. Bring your own food, drinks and lawn chair and enjoy a concert under the stars.
The Norman Rockwell Museum
Norman Rockwell Museum Image via Shutterstock by Brian Logan Photography
The Norman Rockwell Museum is every bit as enchanting as it sounds. The museum includes 10 galleries of changing exhibits that showcase the work of renowned 20th century American illustrator Norman Rockwell.
Rockwell lived his final 25 years in Stockbridge, where the museum is located. Towards the end of his life, he left his local studio and everything in it to the Norman Rockwell Museum. Visitors can view the portion of his studio that was moved to the museum grounds. In the surrounding 36-acre grounds, the museum hosts regular events, festivals and workshops.
Jacob’s Pillow
Jacob’s Pillow is a renowned dance school and performance space that’s best known for its summer dance festival, the longest-running in the world. It features over 500 free performances and events from June through August.
You’ll be just as captivated by the exceptional dance performances as by the gorgeous 225-acre grounds that were declared a National Historic Landmark District in 2003.
Edith Wharton’s Home – The Mount
Edith Wharton’s home, The Mount Image via DepositPhotos by Lee Snider
The Mount was the home of famous American writer, Edith Wharton. She was instrumental in the design of her own mansion and gardens in 1902. A historical landmark, the Mount is also a museum and cultural centre that hosts events throughout the year.
Visitors can view the main house’s magnificent period furnishing, her fine art collection and Wharton’s personal library. A stroll through the pristine gardens is a must. The Italian Garden, French Flower Garden and Rock Garden are gorgeous.
The Clark Institute
The Clark Institute in Williamstown, Massachusetts
The highly revered Clark Art Institute in Williamstown is one of the only global institutions that serves as both an art museum and a distinguished research institution. It was founded in 1950 by Sterling and Francine as a place to house their impressive art collection. It includes works that span from the Renaissance to the 20th century.
The Clark has been open to the public since 1955 and features a variety of rotating art exhibitions, outdoor sculptures and cultural events. Visitors can take their time exploring the museum and walking the grounds. You can also pack or purchase a picnic lunch to enjoy outdoors or dine at the onsite Cafe 7.
The Hancock Shaker Village
The Hancock Shaker Village in Pittsfield is a “living history museum” where visitors of all ages can have fun experiencing a day in the life of the Shaker community.
The museum includes a Shaker Village Collection that displays furniture, tools, household objects and art from the Shaker community. Visitors can explore the farm and gardens and interact with sheep, goats, chickens, pigs and turkeys.
Explore the great outdoors in the Berkshires
Mount Greylock
Path to Mount Greylock in the Berkshires
Mount Greylock is on the list of best Berkshires things to do if you want to get the most amazing mountain-top views. With its summit at 3,492 feet, Mount Greylock is the highest peak in the state of Massachusetts.
Hikers have the option of choosing several trails up to the summit that are all part of the 12,000-acre Massachusetts State Park system. One path includes part of the Appalachian Trail. Visitors can also reach the top on roads that are accessible by bike or motorized vehicle. No matter how you choose to get up there, the view is worth it!
October Mountain State Forest
Fall foliage in the Berkshires, Massachusetts
October Mountain State Forest is the ideal spot if you love the great outdoors. Yes, October Mountain is gorgeous in October as fall paints the landscape in stunning hues of yellow, orange, green and red—but it’s also lovely any time of year.
With over 16,000 acres, October Mountain is Massachusetts’ largest state forest and gives visitors the widest variety of outdoorsy things to do in western Massachusetts.
Its numerous nature trails accommodate every level of hiking experience while lakes and brooks offer opportunities to fish, canoe, kayak and camp. Mountain biking and skiing are other popular options.
Ramblewild Adventure Park
Ramblewild Adventure Park lets you take in all of the Berkshire of Massachusetts beauty from the treetops! As an aerial park, Ramblewild’s treetop adventure trails involve exploring nature with zip lines, brides, ropes, bridges and swings. There are eight aerial trails and a professional guide is with you at all times to ensure a fun and safe experience.
If you’re looking for what to do in the Berkshires as a family, this place is tons of fun for everyone! All aerial park participants must be seven years or older, be at least 55 inches tall and weigh under 265 pounds.
Pleasant Valley Wildlife Sanctuary
Beaver lodge at Pleasant Valley Wildlife Sanctuary, Berkshire Mountains, Massachusetts
Pleasant Valley Wildlife Sanctuary is another massive outdoor lovers’ playground. It’s a 1,200-acre sanctuary that features a variety of trails, meadows, forest and a large pond. Canoeing, bird watching, paddling and other activities are also offered.
For a leisurely hike, the 30-minute flat loop around Pike’s Pond is perfect for beginners and families with young children, who will be thrilled to spot a resident beaver along the way. For hikers seeking an extra challenge, the Trail of the Ledges is a steep 3-mile loop climb to over 2,000 feet to reach the top of Lenox Mountain.
Leaf peeping at the best fall foliage spots in the Berkshires
Ask anyone who’s been to the Berkshires, Massachusetts in the fall about the most spectacular part of their visit. We guarantee that seeing the magnificent foliage will be on their list.
There’s no shortage of amazing fall leaves sightings in and around Berkshires towns and countryside. But one of the best foliage spots to capture a jaw-dropping 360-degree view of the fall-hued landscape is at the summit of Mount Greylock. Be sure to have your camera ready because you’ll want to capture this panorama.
Another spectacular spot for fall foliage viewing that’s popular on every Berkshires road trip is the well-known hairpin turn in North Adams as you’re driving along Route 2. This sharp angle at high elevation offers the perfect opportunity to get a birds-eye view of the valley’s town and intense colors of the fall treetops.
Enjoy winter activities in the Berkshires
Massachusetts Veterans War Memorial Tower on Mount Greylock
With plenty of snow to be had in the winter, snow sports are among the best things to do in the Berkshires. Here are some of the top ski resorts in the Berkshires area:
Jiminy Peak Ski Resort is a massive self-contained mountain resort in Hancock, near Pittsfield. It has a popular village center with shops, restaurants and bars on-site, so it’s a fun place any time of year. But skiing and snowboarding are its main attractions with 45 trails accessible by 9 lifts that accommodate every level of skier from beginner to advanced.
Berkshire East Mountain Resort is a top choice for families because it has so many things to do! For skiers and snowboarders, there are 42 trails and 4 aerial lifts plus 2 surface lifts. For visitors who want lessons, there’s a reputable ski and snowboard school for all ages.
Wachusett Mountain in Princeton, MA is the tallest mountain in the state. The ski resort features 25 trails and 8 lifts with options for all levels of skiers.
Ski Butternut in Great Barrington is another popular ski and snowboard destination. There are 22 trails on 110 acres and a fun 7-lane tubing centre. Butternut also offers ski and snowboard lessons for all ages.
Otis Ridge is a smaller, family-friendly ski resort near Pittsfield. The Ridge features 3 beginner slopes, 4 intermediate and 3 black diamond trails. They have a snow sport school for adult and kids’ lessons, a ski camp for kids and half-day and full-day ski pass options.
Savour the Berkshires’ local food & drink
Residents of the Berkshires take great pride in their local agriculture and family-owned and operated farms, which is why you can find some of the freshest food offerings in the country. If you’re wondering where to eat in the Berkshires, here are some delectable ideas.
Eateries in Lenox:
Chocolate Springs Cafe has become a Lenox local gem since it opened in 2003. A chocolate lover’s paradise, the cafe is beloved for its welcoming atmosphere that has cozy couches and live music in the evenings. But, yes, the chocolate offerings steal the show! Their award-winning hot chocolate is to die for, while their freshly-made truffles, cakes and gelato are equally delectable.
Nudel Restaurant is located in the heart of downtown Lenox and is a prime example of Berkshire’s pride in supporting the region’s harvests. All of their menu items are made with the freshest ingredients sourced from local farms and small food producers. Each day’s menu is chef-crafted and inspired by the most seasonal selections.
Haven Cafe & Bakery in Lenox is a must if you want to savor one of the best breakfast and brunch experiences in the region. This friendly spot is a local favorite for its exceptional coffee and seasonal specials. But you can’t go wrong with the heavenly staples that are always on their menu, like the croissant French toast, breakfast burrito or buttermilk pancakes.
Where to eat in Stockbridge:
Once Upon a Table is a cozy bistro nestled in a small alley in downtown Stockbridge. There you’ll find a delicious lunch and dinner menu with sandwich, salad, seafood and pasta delicacies like crab cakes, ravioli, mac and cheese and quiche. Save room for their amazing profiteroles or creme brûlée.
Where to eat in Pittsfield:
Mazzeo’s Ristorante is a delightful Italian food favorite in Pittsfield. They bake bread everyday and use fresh, local ingredients for all of their dishes. They’re only open for dinner and are usually very busy, so it’s a good idea to make reservations. Their family-size eggplant parmigiana never disappoints!
Where to stay in the Berkshires
Wheatleigh in Stockbridge Image via Shutterstock by T photography
Accommodations in Lenox:
Wheatleigh
One of the best hotels in the Berkshire area is actually a luxurious Gilded Age mansion so exquisite that it was included on the National Register of Historic Places in the early 1980s. Wheatleigh exudes elegance in every way.
Located on 22 acres overlooking the Berkshire mountains, you can’t beat the nature and serenity Wheatleigh offers. The suites are glorious with their fine art and decor, luxury bedding and antique soaking tub. Enjoy fine dining and wine tasting without ever leaving the grounds.
Check rates and availability at Wheatleigh
Hampton Terrace Inn
This upscale, historic bed and breakfast is the ideal spot for a weekend getaway in the Berkshires. It’s perfectly located for the best things to do near Lenox, MA. Downtown Lenox is a short five-minute walk away.
You’ll love the on-site amenities that include a heated outdoor pool, ensuite fireplaces and jetted tubs, and the all-you-can-eat Southern breakfast buffet.
Check rates and availability at the Hampton Terrace Inn
If you have your heart on staying at one of the most upscale wellness resorts in the Berkshires, Canyon Ranch delivers. Guests choose a plan that helps you meet that goal whether your selected topic is wellness, joy, healthy weight or life transitions.
A wellness guide will help you schedule a daily wellness program that includes a variety of classes, lectures and activities—from meditation and Zumba to stand-up paddle boarding and camp archery.
Where to stay in Stockbridge:
The Inn at Stockbridge
Why stay at a regular motel when you can stay at a Georgian style mansion from 1906 that serves as an elegant bed and breakfast? Secluded on six acres in the Berkshire mountains, it’s perfect for a romantic getaway.
Stay cozy in one of the 16 available rooms, many of which have their own fireplace and double whirlpool tub. Or spend some time enjoying a cocktail on the wraparound porch, sunbathe by the pool or simply wander around the gorgeous gardens. With such a lovely place, you’ll never want to leave!
Check rates and availability at the Inn at Stockbridge
Accommodation in Pittsfield
Hotel on North
This quirky boutique hotel located in the heart of Pittsfield is one of the coolest places to stay in the Berkshires. It radiates modern eccentricity while maintaining the rich charm of the Berkshires history.
Hotel on North works with local galleries to feature their own rotating art exhibition right by the front lobby. They repurposed a vintage birdcage elevator into a cocktail table with seating for two. No two hotel rooms look exactly the same. And the hotel is close to everything, so you can’t go wrong!
Check rates and availability at the Hotel on North
Berkshires Map
Final thoughts on the best things to do in the Berkshires
In a region that’s full of rich culture, captivating nature, idyllic landscapes, locally sourced food and eateries, you’ll find no shortage of amazing things to see and do in the Berkshires. Whether you choose to take a weekend getaway or a week-long road trip, you’re guaranteed to fall in love with this magical slice of New England.
So, let your adventurous spirit guide and let the Berkshires delight you with all its charm!
More information
Tourism Info: Berkshires Tourism
Car Rental: Compare prices at Auto Europe (not just for Europe!)
Guidebook: Berkshire Destinations, AMC’s Best Day Hikes in the Berkshires
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