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Posted on October 05, 2022 Written by LocalIQ

Stockbridge Main Street at Christmas. Credit: Courtesy of 1Berkshire, Photo by Joel Laino

There’s no “off” season in the Berkshires. Spring, summer and fall, the region offers endless fun for the whole family. But winter is a time when the Berkshires truly shine. Whether you’re a fan of the cold and snow or prefer to admire it while bundled up and sitting next to a fire indoors, there’s something irresistible about a New England winter. And no place does it better than the Berkshires. 

Read on for can’t-miss events and must-try experiences to help you plan your winter wonderland getaway to the Berkshires.  

Header: Stockbridge Main Street at Christmas. Credit: Courtesy of 1Berkshire, Photo by Joel Laino

Winter markets and local delights

Food just tastes better when you buy it at a farmers market or farmstand. The Berkshire Grown Winter Farmers’ Markets are a series of indoor winter markets highlighting the foods grown and produced in the region. Keep an eye out for details on these must-visit markets , and plan to leave space in the car to bring home seasonal goodies.

TOURISTS’ exterior deck bar. Credit: Courtesy of 1Berkshire, Photo by Nicole Franzen

TOURISTS’ exterior deck bar. Credit: Courtesy of 1Berkshire, Photo by Nicole Franzen

Curl up by a fire with a book and your sweetie

Is there any better way to spend a cold winter evening than at a cozy inn, charming B&B or peaceful local hotel? The Berkshires offer an escape from the stresses of everyday life, so leave plenty of time for R&R. Fill your days with explorations, then spend the evenings relaxing. Bring a book or a knitting project, a journal or a sketchbook. Book a room at Shaker Mill Inn, Race Brook Lodge, Gedney Farm, Guest House at Field Farm, The Constance, Hotel on North, TOURISTS, Seven Hills or any of the unique local hotels, inns and B&Bs

Museum hop or catch a show

One of the best things about the region is that you don’t have to choose between spending time in nature and soaking up arts and culture . It’s easy to do both. 

Even if you’re there for a ski trip, set aside an afternoon to check out the Williams College Museum of Art, The Clark, MASS MoCA or the Norman Rockwell Museum. Or, plan a date night around a show at Berkshire Theater Group, Mahaiwe Performing Arts Center or Barrington Stage Company.

Shop local for unique holiday gifts

With such an emphasis on local culture and a rich arts scene, a weekend in the Berkshires offers ample opportunity to find unique gifts for everyone on your list. Book a girls’ weekend, then wander through small boutiques and funky gift shops in search of the perfect present. Bookmark local spots like Thistle ‘n Thorn Floral, Heirlooms Jewelry, An American Craftsman Gallery, Berkshire Mantiques, Dory & Ginger, Casablanca, Susan Silver Antiques, ROAM: A Xtina Parks Gallery and Nature’s Closet when planning your shopping itinerary

Jiminy Peak in Hancock. Credit: Courtesy of 1Berkshire, Photo by Jiminy Peak.

Jiminy Peak in Hancock. Credit: Courtesy of 1Berkshire, Photo by Jiminy Peak.

Play outdoors in the snow.

Winter sports are what so many people associate with the Berkshires. Whether you prefer thrilling downhill runs at Jiminy Peak, Butternut, Catamount, Berkshire East and Bousquet or want to slide across cross-country trails at Notchview or Maple Corner Farm, this is the place for winter adventurers of all levels. Not into skiing? Strap on a pair of snowshoes at The Clark or any of the properties managed by Berkshire Natural Resources and Trustees of Reservation.

Eat your way through the Berkshires

From cutting-edge local fare to cozy dinners in a local tavern, you’ll find exactly what you crave at the end of any winter’s day. Book a table at local favorite restaurants and bars like Frankie’s Ristorante Italiano, Miss Adams Diner, District Kitchen & Bar, Pleasant and Main, John Andrews Farmhouse Restaurant or The Barn Kitchen & Bar.

Lastly find your perfect holiday event

For kids and the young at heart, Naumkeag Winterlights is a memorable and magical experience featuring thousands of artfully designed light exhibits. You may also want to check out Berkshire Museum’s annual Festival of Trees and The Mount’s NightWood, an outdoor sound and light experience set against the backdrop of Edith Wharton’s home. Visit Stockbridge Main Street at Christmas December 2-4 to witness a magical New England setting reminiscent of a famous holiday painting by Norman Rockwell. Another nostalgic must-see is the Tinseliner Trains with Santa Claus, hosted annually by Berkshire Scenic Railway Museum. Enjoy hot cocoa and roasted marshmallows and a 1950s Christmas train ride with a visit from Santa. For more these holiday ideas and more visit here .

The best part about the Berkshires is that there’s such a wide variety of activities to try. Combine a few of these ideas to create the ultimate winter wonderland weekend getaway!

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