Find Your Winter Fun

Discover the best things to do in the Berkshires in winter, from day trips to cozy weekend getaways.

Outdoor adventures, art and culture, cozy inns—the Berkshires has it all in the winter months, plus vibrant downtowns for shopping and dining. Here’s a short list of ideas for making the most of winter in the Berkshires, from skiing to museum days to chilling by a warm fireplace.

Get Outside

The spectacular natural beauty of the Berkshire hills, just under 3 hours from New York City and Boston, is the perfect setting for experiences that blend New England hospitality with outdoor adventure. Berkshire ski areas have miles of diverse terrain for downhill and cross-country skiing, tubing, and snowboarding. And just because it’s winter doesn’t mean you can’t enjoy a nature walk on the beautiful grounds at cultural venues such as Tanglewood or The Clark. For a uniquely Berkshire outing, take a full-moon hike on the groomed trails at Notchview or a wildlife-tracking walk with a Mass Audubon guide at The Mount. Another great option is Mass Audubon Pleasant Valley Wildlife Sanctuary – check out their All Persons Trail, a mostly flat and easy 20–30-minute walk around Pike’s Pond.

Dining. Credit Kacey Hatch.

Explore the Local Food & Music Scene

After a winter-weather outdoor adventure, what’s better than settling in with a cold brew or belly-warming bite to eat? Head for local favorites Xicohtencatl, Freight Yard Pub & Restaurant, or Mazzeo’s for a delicious dinner and drinks, and The Lion’s Den or Stationery Factory for live music on weekends. Or visit a Berkshire brewpub for a burger and a cold one on tap.  

Shop & Gallery Hop

Winter outdoor activities are weather-permitting in the Berkshires. If you’re looking for an alternative to spending the day outside, there are plenty of interesting shops, independent bookstores, antique co-ops, and art galleries worth a visit. Stop in at local outfitters Nature’s Closet and the Arcadian Shop for a refresh on your cold-weather gear. Or see the latest exhibitions opening at Berkshire museums (free day at MASS MoCA January 25th and free admission to The Clark January through March 2025). Other visual arts galleries of note include Greylock Gallery, ROAM, Sohn Fine Art, and Gary Lichtenstein Editions, among others.

Art class at the Berkshire Art Center. Credit Great Sky Media.

Learn Something New

The possibilities are endless when it comes to educational opportunities in the Berkshires! Want to try your hand at painting or pottery? Sign up for a winter-session class at Berkshire Art Center. Thinking about starting a yoga or meditation practice? Take a workshop at Kripalu Center for Yoga & Health. Enjoy thought-provoking activities and events? Check out the winter offerings at Tanglewood’s Linde Center for Music and Learning, OLLI: Osher Lifelong Learning Institute, or MCLA.

Stay at an Historic Inn (or Mountain Resort)

If a winter getaway in the Berkshires conjures up images of relaxing, rejuvenating (or romance), you’ve got the right idea. From family-friendly suites to intimate fireplaced rooms for couples, there’s a Berkshire inn or resort for winter adventurers like you.

Discover more ways to explore the Berkshires in winter. We’ve got fun ideas for everyone!

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