5 Ways to Have Fun in the Berkshires in Winter

There are no gray days in the Berkshires, even when nights are long and clouds intrude and winter makes its presence obvious. Sure, if you’re just looking with your eyes, you might disagree. But your brain is capable of sensing in so many other ways, and the Berkshires in winter will light up your neurons as few destinations can. With small-town charm and big-city culture, winter sports for novices and adrenaline addicts, and learning experiences that feel more like recess than school, you’re in for a colorful adventure.

5 Ways to Have Fun in the Berkshires in Winter

Get Outside

The Berkshires are Massachusetts’s winter sports capital, where you’ll find beginner slopes and black-diamond trails at popular ski areas such as Berkshire East, Ski Butternut, and Jiminy Peak. Don’t automatically dismiss the idea of zipping downhill just because you’ve never skied or snowboarded, since learners of all ages find these gentle mountains nonintimidating. There are plenty of invigorating alternatives, though, for visitors who want rosy cheeks without snapping on skis. Rent snowshoes at Arcadian Shop or Berkshire Bike and Board, then crunch around Lenox’s Kennedy Park or choose your trail — from easy to challenging — at the Laurel Hill Association’s Stockbridge property. Cross-country ski through fields and forests at rural Canterbury Farm in Becket. Easiest of all: Sit back and let gravity thrill you at one of the region’s snow tubing parks. Snowmaking keeps Ski Butternut’s eight-lane tubing hill primed for fun every winter weekend.

Learn Something New

This isn’t like hitting the books at the start of a semester. In the Berkshires, engaging classes will teach you fun skills and jump-start your creativity. The Education Center at the Berkshire Botanical Garden hosts workshops not only for those who enjoy coaxing new life out of the soil but also for artists, cooks, and kids. One-day, hands-on art classes at the Norman Rockwell Museum allow teens and adults to develop their drawing and painting talents. Kripalu in Stockbridge is your place to journey inward through retreats focused on well-being, creative expression, relationships, meditation, and yoga.

Visit Museums

When you’re lost in the meticulous detail of an original painting or Saturday Evening Post cover at the Norman Rockwell Museum in Stockbridge or in the evocative boldness of a contemporary installation at MASS MoCA in North Adams, you won’t care if the landscape outside looks black and white. Art repositories aren’t the only Berkshires museums that stay open all winter. The Berkshire Museum in Pittsfield, with its array of galleries devoted to art, nature, and innovation, is undergoing dynamic transformation. Interactive experiences, such as those featured within the high-tech Curiosity Incubator, hint at what’s to come. The Mount — the Berkshires’ preeminent historic house museum, where Edith Wharton wrote her most beloved novels — is also open for tours on winter weekends through February. Set as it is in a glorious landscape, the estate is an inspiring place for a winter’s walk or snowshoe trek, as well.

Hear Live Music

Nothing warms a winter night like a spirited musical performance, and in the Berkshires a show is on the calendar every single night. A singer or band plays the Lion’s Den at the Red Lion Inn in Stockbridge 365 days a year. Order a drink and some comfort food, and enjoy this underground pub’s cozy vibe. Thursday nights are reliably lively at the Guthrie Center in Great Barrington, where there’s warm camaraderie among musicians at weekly Hootenannys. And even though Tanglewood is closed for the winter, the Berkshire Bach Society ensures rousing classical music performances are part of the region’s winter scene. Close Encounters with Music brings mesmerizing chamber music performances to Great Barrington stages on select winter nights, too.

Sip Local Wines, Spirits, and Beers

The brewing, distilling, and winemaking scene in the Berkshires ensures you’ll have myriad choices when you’re ready to toast your winter adventures. On winter Fridays and Saturdays, Berkshire Mountain Distillers in Sheffield offers tours of the first distillery opened in the Berkshires since Prohibition’s repeal. Its tasting room’s temptations include locally inspired, small-batch spirits such as Berkshire Bourbon Whiskey, made from corn grown two miles away. If you’d like to sample beers as fresh and inventive as MASS MoCA’s contemporary artworks, Bright Ideas Brewing on the museum’s North Adams campus is your spot for food and brews. At Hilltop Orchards in Richmond, you can rent cross-country skis or snowshoes and explore the property before heading inside for a tasting of Furnace Brook wines. Apple ice wine, made with fruit grown on-site, wouldn’t taste this smooth and sweet without winter’s deep freeze.

What are your favorite ways to enjoy the Berkshires in winter? Let us know!

This post was first published in 2019 and has been updated. 

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