Top 15 Best Things to Do in Great Barrington Massachusetts

You’ll find plenty of things to do in Great Barrington MA, including strolling through its quaint downtown, taking in stunning views from mountain-top hikes, and exploring the town’s theater and fine arts venues. 

An aerial view of Great Barrington MA

Great Barrington is the perfect American small-town get-away – but with a modern flare.

Its walkable downtown is full of red brick buildings that harken to a former era. But the shops, boutiques, and eateries inside are all modern-day – showcasing interesting offerings and contemporary food.

As with all of the Berkshires, art plays a prominent role in Great Barrington. For example, the Mahaiwe Performing Arts Center is an icon in the community – bringing talent from near and far to this town of just over 7,000.

There are also plenty of outdoor activities in Great Barrington, with multiple hikes leading to breathtaking views of the valley below. And winter weather brings skiing and snowboarding on a local family-friendly mountain.

The 15 best things to do in Great Barrington MA

The following are some of the best things to add to your itinerary when visiting Great Barrington, MA.

Discover unique shops and eateries downtown

Downtown Great Barrington - one of the things to do in Great Barrington MA

Great Barrington has a fantastic downtown. It’s big enough to provide a variety of shops, galleries, boutiques, and eateries but small and walkable enough to explore in just a few hours.

One of the more interesting shops downtown is the Railroad Street Collective. This ample space showcases handcrafted items, including distinctive home goods, a wide variety of artisanal jewelry, children’s toys & clothing, ceramics, art, apparel, and gifts. And everything in the store is made by local creatives. (25 Railroad Street)

If you’re looking for unique and well-curated clothing, stop in at Griffin. There’s lots to choose from in this cozy boutique. In addition to clothing, you’ll also find home goods, jewelry, accessories, and other interesting knick-knacks. (4 Railroad Street)

And if you suddenly need ice cream during your stroll, look no further than SoCo Creamery. This ice cream shop, which began in Great Barrington in 2004, features unique and traditional flavors such as Banana Brownie and Blueberry Honey Lavender. (5 Railroad Street)

Visit the Mahaiwe Performing Arts Center

The front of the Mahaiwe performing arts center in Great Barrington Massachusetts

Among the best cultural things to do in Great Barrington MA, is to catch a show or concert at the historic Mahaiwe Performing Arts Center. This beautifully restored theater hosts a variety of performances, including music, theater, comedy, dance, lectures, and film screenings.

The original Mahaiwe Theater was built in 1904, underwent a significant renovation in the 1930s, and again in 2005. From its beginning, the theater sparked an arts culture in the region that now defines the Berkshires.

The box office is open Wednesday through Saturday, 12 PM – 4 PM, and three hours before a performance begins. But tickets can also be purchased on the theater’s website. (14 Castle Street)

Hike Monument Mountain

A view of Monument Mountain in Great Barrington MA

Just a short drive from downtown Great Barrington, Monument Mountain offers a variety of hiking trails that lead to breathtaking views of the Housatonic River Valley at the summit.

In addition to providing a glorious hike, Monument Mountain also carries historic significance. The mountain’s name comes from the Mohican tribe’s stone offerings imbued with prayers left atop its summit. Thus, the name “monument”.

Author Herman Melville is said to have found inspiration for his celebrated novel Moby-Dick here. And William Cullen Bryant found inspiration in his 1815 poem Monument Mountain. Author Nathaniel Hawthorne also spent considerable time on the mountain, finding inspiration for his works.

The mountain is open from sunrise to sunset. There’s a $6 fee for parking except for members of The Trustees of the Reservations, who can park for free. Hiking trail access can be found along Route 183 and Route 7, but the more popular hike is on Route 7. Check the map for more details.

Indulge in farm-to-table dining

A chef holding produce in a field - farm to table dining is a thing to do in Great Barrington MA

Great Barrington and the surrounding area are known for their vibrant farm-to-table dining scene, offering a range of options that celebrate local produce and culinary traditions.

One popular choice is Prairie Whale, an eatery committed to sourcing ingredients from nearby farms, showcasing their seasonal flavors in creatively crafted dishes. (178 Main Street)

A noteworthy establishment just outside of Great Barrington is The Old Inn on the Green, where guests can indulge in a refined farm-to-table experience with dishes that highlight local ingredients, served in a candle-lit room. (134 Hartsville-New Marlborough Road, New Marlborough)

Another option is the delightful Marjoram + Roux, located downtown, which offers breakfast and lunch options made with local ingredients. Be sure to try the farro salad if you’re there for lunch. (47 Railroad Street)

For a casual atmosphere, head to The Bistro Box, a roadside eatery featuring American favorites like hot dogs, burgers, fries, and sandwiches – many using locally sourced ingredients. Open for lunch only. (937 South Main Street)

Visit Bash Bish Falls

A photo of Bish Bash Falls in Great Barrington MA

Nature lovers will want to visit Massachusetts’s highest waterfall, Bash Bish Falls, located southwest of Great Barrington and adjacent to the Mount Washington State Forest. A 30-minute drive will take you to this popular destination featuring water cascading 80 feet into an emerald plunge pool.

While it’s necessary to hike to the falls, the length and difficulty of the hike will be determined by where you park.

If parking in the Massachusetts lot on Falls Road in Mount Washington State Park, the hike will take about .7 miles round trip, but as the terrain is more rugged, this hike is considered moderate to difficult.

Parking is also available in Copake NY, on Route 344. From here, the hike is about 1.5 miles round trip and of moderate ability due to the rocky and uneven nature of the trails.

And if you’re looking for a longer hike? It’s also possible to follow the South Taconic Trail’s 12.4 miles (of moderate to difficult ability) to the falls.

If you’re still interested in more outdoor adventure after seeing the falls, head over to the adjacent Mount Washington State Forest, which features 30 miles of hiking and mountain biking trails, including breathtaking views from the summit of Alander Mountain.

Attend the Berkshire International Film Festival

If you visit Great Barrington in June, check out the Berkshire International Film Festival, featuring over 75 independent and international films, documentaries, and shorts.

This highly anticipated cultural event celebrates the art of cinema. Spanning multiple days, the festival showcases a diverse selection of independent films from around the world, attracting filmmakers and cinephiles alike.

Attendees can engage in thought-provoking discussions, attend screenings, and participate in Q&A sessions with filmmakers, adding a unique interactive element to the experience.

The festival takes place in various venues throughout Great Barrington. Check the website for more information and purchase tickets.

Go skiing or snowboarding

A man skiing in snow

In the winter, a fun thing to do in Great Barrington MA, is hit the slopes at Ski Butternut, a local mountain just a few miles from downtown.

This smaller mountain is a perfect destination for families or anyone eager to ski but not eager for a long drive north.

Skiers and snowboarders of all levels can enjoy the mountain’s 100 acres of trails, which cater to beginners, intermediates, and expert riders. The resort boasts 22 well-groomed trails, ranging from gentle slopes for beginners to challenging runs for more advanced skiers.

In addition to downhill skiing and snowboarding, Ski Butternut also offers tubing lanes for a thrilling alternative winter activity. (380 State Road)

Shop at Berkshire Food Co-op

The outside of the Berkshire Co-op
Photo credit: Kerry Flatley

If you’re interested in local and organic food, check out the Berkshire Food Co-op in Great Barrington.

The Co-op is committed to supporting local farmers and producers and provides a wide selection of high-quality organic and locally sourced products.

From fresh produce and artisanal cheeses to sustainably raised meats and specialty products, the Co-op offers diverse options to cater to several dietary needs and preferences.

You can also get a quick bite to eat in the store’s café, which features freshly prepared meals made with ingredients sourced from local farms. (34 Bridge Street)

Have fun at the Catamount Aerial Adventure Park

A 17-minute drive from downtown Great Barrington toward the New York State border will take you to the Catamount Aerial Adventure Park.

Located within the Catamount Ski Area, the Aerial Adventure Park features a series of aerial courses and challenges set high up in the trees.

Participants navigate various obstacles, such as zip lines, rope bridges, and suspended platforms, while safely harnessed. The park offers nine courses of varying difficulty, ensuring there’s something suitable for beginners and those seeking a more challenging experience.

Tickets to the park allow for 3 hours of climbing. The park is generally open from 10 AM – 5 PM Thursday through Monday. Check the website to verify times and view ticket prices. (17 Catamount Road, South Egremont)

Visit art galleries and studios

The outside of an art gallery in Great Barrington
Photo credit: Kerry Flatley

With its thriving arts scene, it’s not surprising that Great Barrington is home to numerous art galleries and artist studios.

Here are a few worth checking out:

Explore Asiabarong

The outside of Asiabarong - a story that sells antiques and other items from Asia
Photo credit: Kerry Flatley

One of the more unique things to do in Great Barrington MA, is to visit Asiabarong.

Although technically a retail store, Asiabarong could also be mistaken for a museum. Its ample space contains over 25,000 Asian antiques, sculptures, crafts, jewelry, artifacts, and furniture pieces.

Wandering throughout the store, you’ll feel transported to numerous Asian countries simultaneously. There’s everything from a Teak House selling for $22,000 to an antique Japanese literature book selling for $50 to a Korean Hahoe Mask for $90.

Asiabarong is open 11 AM – 5 PM daily except for Tuesdays and Wednesdays. (199 Stockbridge Road)

Enjoy outdoor recreation at Lake Mansfield

Another fun outdoorsy thing to do in Great Barrington MA, is to visit and explore Lake Mansfield.

Numerous hiking trails border the lake and wind through the surrounding woods, making for a picturesque walk.

The lake also provides a perfect spot for fishing, where anglers can cast their lines in search of bass, trout, and other fish species.

Additionally, Lake Mansfield offers a sandy beach area for swimming and sunbathing during the warm summer months. And families can gather for picnics in designated areas using the available picnic tables and grills. (Lake Mansfield Road)

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Explore Bartholomew’s Cobble

If you’re up for more adventures outdoors, visit Bartholomew’s Cobble, a 17-minute drive south of Great Barrington in Sheffield.

This 1,000-foot-high bedrock offers five miles of scenic trails with sweeping mountain vistas and unique geological features.

Bartholomew’s Cobble also hosts various woodland flowers and fern species. So much so that it earned a National Natural Landmark designation in 1971. It’s also home to one of the largest Cottonwood trees in the state.

Admission to Bartholomew’s Cobble is $5 per person and $1 per child (ages 6-12) for non-members. Members of Trustees of the Reservation are free. A visitor’s center and facilities are open seasonally. And a local naturalist leads 2-hour tours on the last Saturday of each month (check the website for more details and register for the tour).

Explore Lenox Massachusetts

Buildings in downtown Lenox MA
Photo credit: Kerry Flatley

About 25 minutes north of Great Barrington is the town of Lenox, MA. Although slightly smaller in size, Lenox packs a big punch in terms of the art and cultural opportunities at its doorstep.

In the early 20th century, Lenox was deemed the “Newport of the Berkshires” due to the many wealthy industrialists who built summer residences here. It’s from this clustering of high society and wealth that a venerable arts scene arose.

Today, you’ll find plenty of cultural things to do in the town, as well as outdoor adventures and esteemed restaurants.

Here are a few highlights of what Lenox has to offer:

  • Tanglewood: the outdoor summer residence of the Boston Symphony Orchestra
  •  The Mount: an opulent Gilded Age mansion and gardens
  •  Lenox Village: although not as large as Great Barrington, Lenox has a cute downtown worth a stroll
  •  Ventfort Hall Mansion and Gilded Age Museum: also a Gilded Age mansion that’s been converted into a museum
  •  Shakespeare & Company: This indoor and outdoor theater performs on-stage performances throughout the year.

To learn more see: Top 15 Best Things to Do in Lenox Massachusetts

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A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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