The Berkshires is a popular vacation destination and with so many fun things to do in Great Barrington Massachusetts, it lands solidly on the list of must-visit small towns in Western MA.
One of the most charming small towns in the Bay State, there are plenty of fantastic things to do in Great Barrington on your next trip to the Berkshires!
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W.E.B. Du Bois, author, sociologist, activist, and founding member of the NAACP, was born in Great Barrington in 1868. Called The Homesite, the home Du Bois was born in is a designated National Historic Landmark.
Visit The Homesite to learn more about Dubois’ legacy and connection to Great Barrington, and then grab a brochure so you can go on the self-guided W.E.B. Du Bois downtown walking tour so you can see the places that shaped his life and work.
Downtown Great Barrington
Editorial credit: Albert Pego / Shutterstock.com
Great Barrington’s lovely downtown has a quintessentially charming New England vibe to it, with cute boutique shops and great restaurants, including the must-visit The Prairie Whale, one of the best restaurants in the Berkshires!
Take a historic walking tour and check out some notable historical sites like the Winged Victory Monument, Searles Castle, and more. If you’re looking for somewhere to stay within walking distance of the town center, check out the Wainwright Inn for an ultra-charming historical B&B experience!
Mahaiwe Performing Arts Center
The Mahaiwe Theatre originally opened its doors in 1905, hosting vaudevillian acts for audiences that delighted in the aesthetics of this gorgeous proscenium theatre. Silent films made their way to Great Barrington around 1914, and Mahaiwe continues to host both live performances and film events on its still stunning stage.
This intimate theatre hosts comedy, music, plays, films, and more, so be sure to check the events calendar to see what’s coming up next on stage at the Mahaiwe.
Housatonic River Walk
If you’d like to stretch your legs a bit with a little walk along the river, head to the recently revitalized Housatonic River Walk.
Offering a simple trail that winds along the mighty Housatonic, the Housatonic River Walk is a nice choice for a stroll spring through fall but is closed during the winter months when the trail becomes impassable due to weather conditions.
Housatonic Flats Trail
For a relaxing little hike, check out the Housatonic Flats Trail, considered one of the best hikes in the Berkshires. A true beginners hike, there’s no need to worry about wearing yourself out on this one because it’s only a mile-long loop!
What it lacks in length, it more than makes up for with nature. Look and listen as this is a popular bird-watching spot, but be sure to bring the bug spray with you as it can get a little buggy!
One of the top things to do in Great Barrington during the winter is to head to Ski Butternut, where you will find 100 skiable acres, snowboarding terrain parks, and snow tubing trails with 100% snowmaking capabilities!
If you aren’t traveling with all of your equipment, don’t worry; you can rent it all right there when you get your ski pass for the day. Trails range from beginner to advanced, so there’s something for all skill levels at Ski Butternut.
Lake Mansfield is a beautiful 29-acre pond that is a favorite swimming spot for locals and visitors alike! Lifeguards are present May through Labor Day, and many come to enjoy the sweet serenity of this space and cool off during the humid summer months.
In addition to the sandy beach, there are also picnic facilities and nature trails, so even if it’s not quite swimming weather, Lake Mansfield is still a great spot to go out and enjoy a little peace and quiet.
The Guthrie Center
The Guthrie Center is located in the church of Arlo Guthrie’s “Alice’s Restaurant” fame, and was founded in 1991 as an inter-faith center that focuses on community development through programs like free lunches, workshops, musical lending libraries, and more!
An absolute must-visit for anyone who has ever listened to and loved Arlo Guthrie’s epic 18+ minute song, the Guthrie Center also hosts a weekly hootenanny every Thursday evening; check in with the calendar to see what to expect during your visit!
Beautiful Monument Mountain is a popular thing to do in Great Barrington partly due to the gorgeousness of the views (especially in fall!) afforded you once you climb to its 1,624-foot summit, and partly due to its very cool place in literary history.
It is said that the inspiration for the story of Moby Dick was born on Monument Mountain when Herman Melville and Nathaniel Hawthorne found themselves sheltering in a cave together during inclement weather; this mighty mountain may have also been the birthplace for one of the greatest stories in American literary history!
Taft Farms is a lovely little family farm that welcomes the public in to visit their farm animals and participate in their youth community garden. They also host a fantastic Christmas tree farm and are considered one of the best pumpkin patches in Massachusetts!
Taft Farms also offers fresh produce and other tasty goodies in their Farmhouse Kitchen and Deli. Taft Farms also specializes in baked goods like apple cider donuts and fresh-baked seasonal pies, so there’s something for everyone to enjoy out at Taft Farms!
Beartown State Forest
Beautiful Beartown State Forest is 12,000+ acres and spans several towns, including Great Barrington. This wonderfully maintained state forest has great hiking trails; Benedict Pond Loop Trail is a lovely 1.7-mile loop around the lake, and a lovely hike any time of year.
Beartown State Forest makes for a fantastic picnic spot, too. Take your favorite lunch out and find the perfect spot to relax and take it all in!
There are lots of fun things to do in Great Barrington Massachusetts, so be sure to swing by during your next Berkshires vacation!
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Amy Hartle is the founder and Editor-in-Chief of New England With Love, a comprehensive resource for travel in the New England region. Amy has been exploring New England since 2001. She lived in Vermont for many years and is a graduate of Plymouth State University in New Hampshire. Amy has been writing about travel for over a decade. On this site, Amy aims to share her love of New England and help you to have the best possible adventures!
Amy has been a full time blogger since 2012, and is also the publisher of Two Drifters, where she writes about couples travel and relationships, as well as Let’s Adventure Baby, a family travel site. When not traveling the world or creating epic blog content, Amy can be found cuddling with her husband, son, and cats, & drinking a maple latte.