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Holidays & Beyond

Posted on September 06, 2022Written by 1Berkshire Marketing Team

Things to do in the Berkshires in the winter.

It’s Time to Plan Your Festive Winter Getaway to the Berkshires

Sparkling snowcapped mountains. A crackling fire in the hearth. A glass of warm apple cider. Winter is a magical season in the Berkshires offering chilly outdoor fun and cozy indoor retreats where you can rest and recharge for the next day’s adventure. Ski in the morning. Stroll through a world class museum in the afternoon. Catch a concert after a hearty meal. There’s something for everyone in the Berkshires! Learn more about visiting in the winter.

Explore Winter Events in the Berkshires

  • Festival of Trees – Hosted annually by Berkshire Museum, the Festival of Trees showcases dozens of artfully designed holiday trees around a specific theme. Each tree is decorated by a Berkshire business, organization, or group. It’s a fun holiday exhibit to add to your itinerary! 2022 Festival dates not yet announced.
  • Naumkeag Winterlights – Bring the whole family for a magical, fun, and safe outdoor experience – with food, refreshments, and more – at Naumkeag. See the historic property sparkle with thousands of shimmering, artfully designed holiday lights. Details for 2022 have not yet been announced.
  • NightWood – Beginning in November, NightWood is an outdoor sound and light experience set against the backdrop of The Mount, Edith Wharton’s home. The total route is approximately 3/4 of a mile through the woods and gardens and includes both paved and unpaved pathways, inclines, and stairs. Enjoy a mesmerizing light installation while listening to a curated soundscape to enhance the experience. 2022 dates are November 11-January 1.
  • Berkshire Grown Winter Farmers’ Market – Indoor winter markets will feature the abundance of local grown and produced foods found in the Berkshires. Details to be announced.
  • Tinseliner Trains with Santa Claus hosted by Berkshire Scenic Railway Museum – Enjoy a 1950’s Christmas train ride with a visit from Santa. Trip includes a layover at the PopCares Tree Lot to pick a tree for pick up later. Also, enjoy hot cocoa and roasted marshmallows.
  • Stockbridge Main Street at Christmas – The town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas.

Find Fun Things to Do in Berkshire Winter

  • Play outdoors in the snow – Choose thrilling downhill runs at a ski resort such as Jiminy Peak, Ski Butternut, Catamount, Berkshire East, and Bousquet. Choose the deeply satisfying slide on cross-country skis at picturesque Notchview or Maple Corner Farm. Or strap on a pair of snowshoes and become part of a glorious winter landscape on the grounds at The Clark or any of our Berkshire Natural Resources Council and Trustees of Reservation properties.
  • Explore Culture Indoors – Check out the Williams College Museum of Art, MASS MoCA, and the Norman Rockwell Museum, or you might enjoy catching a show at Berkshire Theater Group, Mahaiwe Performing Arts Center, and Barrington Stage Company. 
  • Satisfy Your Inner Foodie – Settle down to a cozy dinner in a local tavern, or splurge at one of the more elegant fine dining establishments – both make for a perfect ending to a winter’s day. Some ideas include Frankie’s Ristorante Italiano, Miss Adams Diner, District Kitchen & Bar, Pleasant and Main, John Andrews Farmhouse Restaurant, The Barn Kitchen & Bar. 
  • Cozy Up by the Fire – Nothing beats a cozy inn, charming B&B, or peaceful hotel. After a long day exploring the Berkshires, relax and recharge at one of our many excellent lodging options. Some ideas include Shaker Mill Inn, Race Brook Lodge, Gedney Farm, Guest House at Field Farm, The Constance, Hotel on North, TOURISTS, and Seven Hills. 
  • Gift Giving – Don’t forget this is the perfect time of year to pick up gifts for your loved ones or treat yourself to something sparkly to put you in the holiday spirit. From small boutiques to funky gift shops, you are sure to find that perfect something in the Berkshires. Ideas include 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.

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