21 Best Things to Do in the Berkshires

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The Berkshires are a mountain range extending the western length of Massachusetts and spilling into nearby states. Sprinkled throughout the region are small towns and cities awaiting exploration. The Berkshires have it all – adventure, solitude, romance, culture, and more. Situated just a few hours’ drive from two major cities, New York and Boston, this area is pastoral but within reach.

With ample activity offerings and places to sightsee, it’s the perfect place to visit in New England if you’re looking for a charming and sophisticated getaway that’s remote yet accessible. Let’s take a lo9ok at 21 wonderful things to do in the Berkshires of New England!

Play in the Great Outdoors!

If the trails are your respite of choice, then the Berkshires will satisfy any craving for nature. Climb the highest peak in the state or take a more casual ride along a rail trail. The Berkshires are an outdoor paradise; any choice will lift spirits and fill you with a sense of awe.

Mount Greylock, Adams

A tree with a mountain in the background

At 3491 feet, Mount Greylock is the highest peak in Massachusetts. Part of the Massachusetts State Park system, it is composed of 12,000 acres and a well-maintained trail network through the Berkshires and Taconic mountain ranges. Several trails lead to the summit, including a stretch of the Appalachian Trail, which runs through the park. An accessible road used by both motorized vehicles and bicycles also leads visitors to the top, so you can choose your own adventure.

Once you’re at the summit, you’ll be greeted with views of up to 90 miles away, as well as stunning views of nearer farms, forests, and towns. To cap off your visit, climb the 93-foot Veterans War Memorial Tower or grab a bit to eat at Bascom Lodge.

Ashuwillticook Branch Rail Trail

An open wooden fence on a path in the woods

The Ashuwillticook Branch Rail Trail runs for thirteen miles from Lanesborough northward to Adams, with an extension south to Pittsfield underway and a northward one being planned. Whether walking, jogging, biking, or rollerblading appeals to you, this railroad-ground (flat!) trail will serve you well. Along the way, you’ll pass by wetlands where you may spy turtles and fish, a reservoir with stunning views of the surrounding mountains from the shores, and a peaceful forest.

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Natural Bridge State Park, North Adams

A close up of a lush green bushes and a rock wall

For a state park with opportunities that will suit the interests and capabilities of everyone in your party, visit Natural Bridge, located in North Adams. The park’s namesake is a natural marble geological formation, in addition to a marble quarry. Visitors can view the features from wooden bridges, pathways, and viewing platforms.

The chasm has just a quarter mile of walking, but there’s a lot to see. Besides the main attraction, Natural Bridge State Park has a gorgeous field below the walking area – the ideal place to have a picnic lunch. Seasonal programming is offered by park rangers and interpretive signage is posted year round, giving visitors ample opportunities to learn about the historic, geological, and human impact of the area.

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Leaf Peeping

Aerial view of fall trees with a highway in the center

The Berkshires are home to some of the best leaf peeping around! While driving anywhere in this region will give you sights of fall’s most stunning colors, the iconic hairpin turn along Route 2 in North Adams offers unbelievable views. Besides views of spectacular foliage from a high elevation, this point will give you views of the surrounding valley towns.

Another superb destination for leaf peeping is the top of Mount Greylock, where the high ground will give you the advantage of taking in 360-degree views. Wherever you take a roadtrip in western Mass in the fall, you’ll be on an impromptu leaf peeping expedition, so keep your eyes wide open!

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October Mountain State Forest, Lee

A sandy beach area in front of a body of water with fall trees in the distance

Lovely any time of the year, October Mountain offers over 16,000 acres along with miles of excellent and varied hiking. For hikers seeking a moderate trek, the October Mountain Loop Trail will not disappoint. It tends to be less busy than some of the more popular trails, and features brooks and a lake, making it ideal for a calm yet energizing time in the woods.

For a less strenuous hike, try Washington Mountain Marsh interpretive trail. This two-mile trek will take you through a unique area, with features including marshlands, wetlands, an overlook, remains of nineteenth-century houses, a cemetery, and of course, animal habitats. If you’re searching for another adventure, October Mountain State Forest offers camping, places to canoe or kayak, and opportunities to fish, mountain bike, and cross-country ski.

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Jiminy Peak Mountain Resort, Hancock

Ski trails in the summer with green trees between each trail
Jiminy Peak in the summer

If hitting the powder is your winter activity of choice, then spend a day at Jiminy Peak. With 45 trails that provide a variety of routes for skiers and snowboarders of all difficulty levels, you won’t get bored during your time on the mountain. With numerous trails open for night skiing, the fun can really last all day long! Once your time on the slopes is over, head to the lodge to warm up, or reserve a stay at the Country Inn. The Country Store on site also has a deli and snacks, plus local specialities and souvenirs. 

Visiting in summer? There’s also plenty to do, like aerial adventure courses, mountain biking, and more.

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Arts and Culture

The Berkshires are an artist’s – and an art lover’s – oasis. Artists spanning a breadth of creative pursuits, including music, dance, performance, writing, painting, drawing, and beyond, have flocked here for generations, both for inspiration and for opportunities to showcase their work.

Norman Rockwell Museum, Stockbridge

A red house with a green lawn and mountains in the background
Editorial credit: James Kirkikis / Shutterstock.com

Stockbridge, MA was home to Norman Rockwell, an icon of 20th century American illustration art, for twenty-five years. Here, a museum was established in his honor in 1969. This temple to Rockwell’s work offers a deep dive into this life, highlighting his artistic growth, how he posthumously became the state artist of Massachusetts, and the societal impact of his popular illustrations. The museum is dedicated to equity, and it illuminates the connections between art and justice through its exhibits and programs. Learn more about the Normal Rockwell museum here.

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Tanglewood, Lenox

People sitting in lawn chairs at dusk
Editorial credit: T photography / Shutterstock.com

Tanglewood is best known as the summer home of the Boston Symphony Orchestra. Situated in the beautiful hills of the Berkshires, it offers orchestral concerts and many other performances all summer long. With performances by the Boston Symphony Orchestra and the Boston Pops, as well as choral groups and popular artists, your visit will be a feast for the ears.

Looking downward on a green hill with mountains in the distance
Editorial credit: T photography / Shutterstock.com

Besides the incredible music you can take in at one of three concert venues, Tanglewood has a lush and landscaped property with gardens, sculptures, and views of the mountains – the perfect place for a romantic stroll!

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MASS MoCA, North Adams

MASS MoCA (or, the Massachusetts Museum of Contemporary Art), is tucked away in the northwesternmost corner of the state. Once you step inside, you’ll discover what a gem it is. You’ll want to set aside a good part of a day for your visit; with 16 buildings, you’ll need some time to truly experience it!

Steps leading up to a building with mountains behind it
Editorial credit: T photography / Shutterstock.com

Opened in 1999, its ever-expanding footprint includes recent renovations that create more space for art and create even more impact. With cafes, a full restaurant, and even a microbrewery, there are plenty of opportunities to stay nourished and enjoy your day! Besides its stellar and immersive visual arts, MASS MoCA also has performing arts spaces. Be sure to check the calendar to see if an event is happening during your visit.

The Bookloft, Great Barrington

If reading is your entertainment of choice, then a visit to the Bookloft will bring you immense joy. This independent bookstore, located in Great Barrington and open since 1974, recently moved into a new location. The comfy shop is a haven for literature lovers; its shelves feature popular bestsellers while highlighting local authors, who are often featured at events held at the Bookloft. The Bookloft is also a great spot to pick up local gifts!

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The Berkshire Museum, Pittsfield

The Berkshire Museum in Pittsfield is over a century old and located centrally in the largest city in the Berkshires. Its exhibits are eccentric and worldly, spanning art, history, and natural science. The collections reveal the museum founder’s goal of bringing the world to the people of rural western Massachusetts; when you visit, you can learn about and see Asian, Native American, and American art, ancient civilizations, sculptures, minerals, natural science, and an aquarium! 

Hancock Shaker Village, Pittsfield

A herd of sheep grazing with a house and round building behind them

The Hancock Shaker Village is the site of an established Shaker community that existed for nearly two centuries. Today, it’s an interpretive site on the National Register of Historic Places, where visitors can learn experientially about the Shaker story. Visitors can explore the museum, buildings, farm, and gardens, and even go on a hike. At over 750 acres in size, the Hancock Shaker Village is a respite from the hectic nature of 21st century life. Before you leave, be sure to stop by Shaker Mercantile for traditional and modern gifts and goods. 

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Clark Art Institute, Williamstown

A body of water reflecting the trees
Editorial credit: quiggyt4 / Shutterstock.com

Set against a luminous backdrop of forest, the marble Clark Art Institute is an art museum and research center. The Clark’s collection comprises works from the Renaissance through the twentieth century, with an emphasis on American and European decorative arts. Visitors will also enjoy special exhibits, which are refreshed throughout the year. Moreover, outdoor art exhibits make the museum’s pastoral setting part of the experience, and visitors will enjoy engaging fully with the Berkshires while taking in the works that are set outside.

Edith Wharton’s The Mount

A villa set up high on a hill
Editorial credit: T photography / Shutterstock.com

Writer Edith Wharton lived at The Mount for a decade during some of the most prolific years of her writing career. Readers, architecture aficionados, and history-loving travelers alike will savor a trip to The Mount. Indoors and out, a step onto the property will make evident how it was a place that inspired significant writing in Wharton. When you visit, you’ll have a chance to take a tour of the house, wander its Italian-inspired garden, and participate in programs for visitors.

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Dining in the Berkshires

With all the sights to see and activities to participate in, you’ll surely be looking for a place to grab a snack, drink, or a full meal. Choose one of these dining destinations and you won’t be disappointed!

Haven Café & Bakery, Lenox

Head to Haven Cafe & Bakery in Lenox for one of the best breakfast and brunch menus around! With seasonal specials and mouthwatering staples, you’ll enjoy whatever you choose at this friendly, unpretentious place. From breakfast burritos to croissant French toast to a wealth of baked goods, your palette will be glad you chose the Haven’s heavenly creations.

Chocolate Springs Cafe, Lenox

Step inside this Lenox cafe and your senses will be captivated by the smells and sights steeped into the walls of Chocolate Springs Cafe. With a wide menu of chocolate products from truffles to hot chocolate and nearly everything in between, you can order some to enjoy in the comfortable atmosphere — and take some to go. Be sure to check the schedule, as live music and events occur throughout the year. 

Hilltop Orchards, Richmond

Hilltop Orchards is an experience. No matter the time of year you visit, you’ll be in for fun, good eats, savory sips, and an engaging time all around. Better yet? Hilltop Orchards is committed to sustainable farming practices! Visitors can take a walk through the orchards or the property’s trails, pick apples seasonally, and participate in a cider or wine tasting at Hilltop’s Furnace Brook Winery. Be sure to swing by the farm store for the best apple cider donuts, seasonal produce, cider and wine, and other local goods.

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The Prairie Whale, Great Barrington

The Prairie Whale offers a rural dining experience influenced by its New York City-owner’s culinary roots. Committed to sourcing its ingredients locally, the changing menu reflects its farm-to-table ethos. It is a popular destination, but even if there’s a wait before you’re seated, the lawn games available will entertain you and make the time fly. 

Berkshire Mountain Bakery, Housatonic and Pittsfield

With an owner who’s featured in Netflix’s Cooked, you know you’re in for a real treat when you set foot inside Berkshire Mountain Bakery! Applying European-style techniques, the business specializes in bread, but its Pittsfield location has a wider menu with pizza, salads, and more. Its homey style is unassuming, but once you take a bite, you will know firsthand the genuine passion for crafting experiential eating that is baked into the products. You might just  want to grab an extra loaf to go!

Barrington Brewery and Restaurant, Barrington

Open in 1995, Barrington Brewery and Restaurant serves solar-brewed beer and locally-sourced fare. With excellent service, satisfying beverages, tasty meals, and a wonderful space indoors and out, a visit here will provide a homey, pleasurable time. Its extensive menu and filling portions make Barrington Brewery and Restaurant an especially good dinner spot if you’ve had an active day.

Tunnel City Coffee, Williamstown

Located in downtown Willamstown, a college town on the Massachusetts-Vermont border, Tunnel City Coffee is the best place around to get a cup of strong, savory coffee. Grab a pastry along with your cup of joe and enjoy it while sitting indoors or outside, where you can take in views of the surrounding mountains or windowshop. 

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