Slice of Life: What living in Great Barrington, MA is like

Considering making Great Barrington your future home? By some accounts the Best Small Town in America, Great Barrington is a truly special gem in south county with a thriving cultural scene. Located about 2.5 hours from both New York and Boston, this town has plenty going on to keep “big city” folk from being bored while still offering the best aspects of small town life. No matter what you’re into, Great Barrington has lots to offer. 

Outdoor Activities to do around Great Barrington

Hikes & Walks

Great Barrington and the surrounding area is teeming with opportunities to get outside, from the relaxed meander of the self-guided W.E.B Dubois historical walk to multi-day journeys in the Appalachian mountains. Hike to the top of Monument Mountain and soak in the breathtaking views of the Housatonic River Valley.

Skiing & Snowboarding

Great Barrington is home to Ski Butternut, a resort with trails fit for beginners to advanced skiers. Additionally, Butternut hosts two terrain parks: one is designed to be smaller for those just getting into riding park or who want to practice their skills on more approachable terrain. Catamount Mountain Resort is a quick ride away on the New York Border, and Jiminy Peak as well as Bousquet are all within your reach in less than an hour’s drive. There’s no shortage of mountains to explore when you make Great Barrington your home base. 

On the Water

Idyllic lakeside living is well within your reach in Great Barrington. Just outside of downtown, you’ll find Lake Mansfield, a 29-acre pond that’s perfect for swimming, fishing or a scenic walk along the water. Bring your camera along when walking along the Housatonic river, or when you discover Bash Bish Falls after a half hour’s drive south. Those seeking larger bodies of water to sail, kayak or cruise along can enjoy Stockbridge Bowl, Laurel Lake, Lake Garfield or Lake Buel, to name just a few of the options within your close reach. 

Great Barrigton’s Arts & Culture Scene

Berkshire Busk!

Every weekend during the summer, Great Barrington hosts a music and street performer festival throughout its downtown. Railroad Street becomes a community gathering point as attendees shop at an evening artisan market, dine outdoors on the closed street, and watch world-class performers perform for tips. You can read more about the festival here.

Mahaiwe Performing Arts Center

The Mahaiwe is a cultural institution right in the heart of Great Barrington. You never know who you might find onstage at the Mahaiwe next. In recent years the venue has hosted comedians like John Mulaney and Cecily Strong, dance exhibitions from contemporary to ballet, theatrical performances, movie screenings, and music from opera to Graham Nash and everything in between. You can count on the Mahaiwe to deliver something extraordinary to watch year-round.

Other Nearby Music & Theatre Venues

Besides the Mahaiwe, there’s a number of venues within reach to suit any taste. In Great Barrington, you can drive 50 minutes or less to any of the following:

The Egremont Barn

The Egremont Barn boosts the best local talent and brings in plenty of out-of-towners that are sure to get you on your foot. The Barn is no stranger to karaoke, either, if you want to get onstage yourself. 

The Foundry

Up in West Stockbridge, you’ll find The Foundry, who are sure to host an out-of-the-box musical or dance performance within their cozy venue. You may even find the odd comedian or two on their events calendar. 


Of course, the venue that needs no introduction in the Berkshires is Tanglewood, the summer home of the Boston Symphony Orchestra. This Lenox institution is famous for incredible classical music as well as chart-topping rock bands and pop artists. Once you become a Berkshire local, you’ll have to spend at least one Fourth of July packing a picnic on the Tanglewood lawn and catching a performance by James Taylor, complete with fireworks in the finale. 

Theatrical Stages

It’s no secret that the Berkshires is teeming with talent in the world of theater, either; Shakespeare & Company in Lenox is sure to have household name in its program each summer. Berkshire Theatre Group has a number of stages nearby for their yearly plays and musicals, including The Unicorn Theatre in Stockbridge and The Colonial Theatre in Pittsfield. Just down the street from the Colonial you’ll also find Barrington Stage Company, who are known for hosting world-class talent and showcasing groundbreaking new material. The Broadway play-turned-film “American Son” premiered with Barrington Stage in 2016. 

Jacob’s Pillow

Take a half hour drive into rural Becket and discover Jacob’s Pillow, a cultural haven that hosts dancers from all over the world. You can catch a groundbreaking performance onstage, or don your legwarmers and check out their community classes for dancers of all experience levels. With plenty of talk-backs, parties and workshops to attend during the summer, any artist moving to the Berkshires is sure to find a community of like minded people to connect with and be inspired by.

The Triplex Cinema & Berkshire International Film Festival 

Film junkies will fit right into the Great Barrington culture–did you know that Indiana Jones star Karen Allen has a clothing store in the middle of downtown? It sits just around the corner of The Triplex Cinema, which (when not under renovation) hosts everything from the latest blockbuster to indie films fresh off of Cannes. Great Barrington is even home to its own Berkshire International Film Festival. BIFF hosts a number of groundbreaking films, talk backs and special events. As a Great Barrington local, you’ll begin to measure the start of the summer by heading downtown for the festival each June. 

Local Galleries

Why not source the art for your new home right from your new town? Main Street and Railroad Street in Great Barrington host an impressive number of fine art galleries, from The Vault to Bernay and more. Take a walk through to check out their latest exhibiting artists and see what speaks to you. 

A Scenic & Lively Downtown

Great Barrington Farmers Market

Your idyllic new lifestyle in Great Barrington simply has to include a stroll around the farmers market on Saturday mornings during the warm months. Peruse craft goods and grab some fresh, locally sourced groceries to set your week up right. 

Boutique Storefronts

There’s plenty of fun to be had when going on a shopping spree downtown. Vintage barware, chic clothing, charming home decor and more are sure to catch your eye when walking the streets of Great Barrington. Hosting a housewarming party? You’re sure to find some unique additions to your new space–along with some outstanding cheese and wine–in your walk around the block. Don’t forget to grab a rare vinyl courtesy of Rob’s Records to get the mood just right. 

Best Places to Eat in Great Barrington

Breakfast & Lunch

When you become a Great Barrington resident, you have your pick of outstanding cafes to become a regular at for your morning cup of coffee. Fuel, Patisserie, Marjoram & Roux, and GB Eats are just a few of your options within a square mile radius downtown, Really, there’s no bad apple in the bunch when it comes to espresso, pastries, and light lunch fare to get you through the start of your day. You’re bound to become friendly with other locals as you see the same faces reading, writing and taking meetings in the ambiance of their favorite coffee shop. 


Great Barrington hosts an impressive array of eateries representing all different types of cultural dishes. Play it close to home with the farm-to-table creations of Prairie Whale, the upscale New England dishes of The Elm, or branch out with Bizen’s sushi or Steam’s ramen dishes. Those who seek a good steak house won’t be disappointed by hitting Number Ten on their way to the Mahaiwe. 

Bars & Dessert

Sometimes you just need to treat yourself–and in Great Barrington, it’s easy to do so with your family, your date, or even on your own. Kids and kids-at-heart will be stunned by the array of sweets available at Robin’s Candy on Main Street. At Robin’s, you can find locally made fudge, sweets from abroad to quell any expatriate’s homesickness, and candies both classic and new. 


If ice cream is your craving, SoCo Creamery is simply the best. From classic flavors, to artisan creations like Lemon Basil or Marzipan Date Orange Zest (don’t knock it til you try it), the quality of SoCo’s creations is unbeatable. They always have a good list of dairy-free flavors and sorbets on hand, too. 


If your tastes are less high-in-calorie and more high-in-alcohol, Mooncloud is arguably the best cocktail bar in the county just on inventory alone. Their list of internationally-sourced liquors is sure to have whatever it is you’re looking for–and if it gets too overwhelming, you just can’t go wrong with one of their craft cocktails. 

Family-Friendly Activities

Grover’s Corner

Hidden behind town hall is Grover’s corner, named in memory of Arlo Guthrie’s former guitarist and legendary local children’s performer, David Grover. The park & gazebo at Grover’s Corner frequently hosts free concerts sponsored by the town of Great Barrington throughout the summer, with children’s programming every Saturday morning in July and August. 

Great Barrington Library

From ice cream parties to outdoor experiences and more, there’s tons of opportunities through the local library to get your kids engaged in their new community.  Stop in and see what’s new to join in on. 

Community Events

You can find an event that’s fun for the whole family no matter the time of year. Besides the aforementioned Berkshire Busk!, you can expect a winter wonderland with the Holiday Shop, Sip & Stroll each December. Adult wreath-making, s’mores by the fire, live music and even a visit from Santa are highlights that return year after year. 


Whatever you’re looking for, Great Barrington is a fantastic place to live! Take a look at the properties currently listed in Great Barrington.

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