There's Always Something Wonderful Here at Saint James Place!

Is Great Barrington Worth Visiting in The Winter? 5 Activities To Do ASAP

If you’re from out of state—or just outside of Berkshire County—you might wonder “Is Great Barrington Worth Visiting in the Winter?” The answer is yes! Below we list 5 activities to do ASAP in Great Barrington in the winter.

Do you know that Downtown Great Barrington is designated at a cultural district? The Great Barrington Downtown Cultural District says, “Not many small towns are lucky enough to boast such a high concentration of creative food, entertainment, art, shopping, and wellness experiences within a walkable half-mile radius.” It’s true! 

Here’s a Google map of the cultural district’s arts & culture, food and drink, health and wellness, and more.

Here’s a Chronogram article “Getting to Know Great Barrington: Small Town Charm” that gives a great overview of Great Barrington’s spirit, people, cultural events, and businesses—whatever the season.

5 Activities to do ASAP in Great Barrington Now

  1. Ski, Snow Shoe and Hike!

    Some winters are AMAZING for snow…others, not so much. Our local ski resorts work hard to groom, create snow, and offer fun opportunities. Check out Butternut (condition report featured), Catamount and Bousquet

    There are so many scenic locations right in and around Great Barrington with beautiful trails, views, and gentle quietude perfect for individuals and families. The Briarcliff Motel compiled a great list of outdoor activities. Go check it out.There are many hotels, motels, bed and breakfasts, inns, and vacation rentals right in Great Barrington and close to what you want to do. The Southern Berkshire Chamber of Commerce has a great list of places to stay. Start with this list.

  2. Attend Amazing Performances and Other Activities!

    Here at Saint James Place (we’re an arts and culture center in the heart of Great Barrington), we have events such as the Winter Great Barrington Arts Markets, chamber music, and opera concerts. Check out our schedule here.You can find a list of winter/early spring events at We also suggest you hop to the Mahaiwe Performing Arts Center website. And how about some Shakespeare and other theater offerings at Shakespeare & Co?

    More of a nightlife live music fan? We suggest you check out the Egremont Barn’s schedule and The Red Lion Inn’s The Lion’s Den. Also, The Berkshire Edge has a great list of local events.

    If you’re fortunate enough to be in Great Barrington in early December (usually the second Saturday), you’ll enjoy the Southern Berkshire Chamber’s Holiday Shop, Sip and Stroll. There are tons of activities for the kids and adults. You can enjoy evening shopping, wreath making, bites and sips at real estate offices, ice sculpting, and fireworks. Saint James Place hosts two free events: Charlie’s Trains (an amazing model train village) and a Vocalis Youth Choir performance.

  3. Shop Downtown Great Barrington!

    Honestly, there’s no better way to get to know Great Barrington than to shop downtown. There are dozens of charming stores to explore from clothing to jewelry; cheese to wine; gift shops to artisan galleries. Here’s list of shops in Great Barrington and the surrounding Southern Berkshire towns.

  4. Dine at Delicious Restaurants!

    Love farm to table dining? Prefer diners and local favorites? Just looking for a great breakfast or quick lunch? Great Barrington has it all. There’s dining on Main Street, Railroad Street, and on Stockbridge Road.Locavore dining with a comfortable atmosphere? We recommend Café Adam, Prairie Whale, and Number 10, all in Great Barrington. Number 10 is the closest to Saint James Place and the Mahaiwe.Cool Cocktails? Mooncloud offers artisan cocktails, bar snacks, and desserts at the top of Railroad Street. Local vibes? We recommend The Well and Miller’s Pub on Main Street. Like Margaritas? There are several delicious Mexican restaurants, including Xicohtencatl, Agaves Mexican Grill, and Fiesta Bar and Grill.

    Here’s a pretty good list of Great Barrington restaurants. And you know how TripAdvisor, Yelp, Open Table, Eater and more work. You’ll find lots of rave reviews.

  5. Explore Great Barrington’s History!

    Do you know that Great Barrington is the home of W.E.B Du Bois, the great African-American historian, sociologist, historian, and civil rights activist? Great Barrington offers an African American Heritage Trail, the Clinton AME Zion Church (part of the Great Barrington Walking Tour and soon to be the African American Culture and Heritage Center), and W.E.B Du Bois’s birth place. Here’s info on a walking tour.You can also visit the Great Barrington Historical Society.Here’s a walking tour map from the Town of Great Barrington.

We shared a lot of information and links. Hope you find it helpful. Come visit Great Barrington this winter (or spring, summer or fall!). Attend a performance here at Saint James Place. There’s always something to do.