Our Favorite Christmas Events in the Berkshires

Whether you're in town for the weekend or Berkshires-born-and-raised, celebrating Christmas here is unmatched. When you walk the wreath-lined streets and catch wind of a caroler in the distance, you'll realize it, too. Read our guide so you don't miss a joyous moment in Massachusetts this season.

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View Norman Rockwell’s Main Street Holiday Village

Known for Home for Christmas, a stunning painting of a snowy Stockbridge Main Street, Norman Rockwell captured the essence of small-town celebrations. All month long, the Norman Rockwell Museum (originally the Old Corner House, which stands at the left border of the painting) will pay homage to the artist. Plan a quick trip to see a miniature display of his winter scene. It's set up around a soaring pine tree and circled by a chugging little train. 

Enjoy A Christmas Carol

The Berkshire Theatre Group brings you A Christmas Carol—back on its original stage at The Unicorn Theatre! This timeless tale of Ebenezer Scrooge, an infamous miser reformed by four spirits, including Christmas Past, Present, and Yet to Come, is a tradition the entire family can enjoy. Experience this classic story filled with holiday carols and the wonderment of the season—only in Stockbridge. 

Experience NightWood at The Mount

Set at famed author Edith Wharton's historic home, NightWood dazzles guests with immersive sounds and lights. This winter, wander the 3/4-mile route through woods and gardens to experience wonder and merriment.

Wander Around Naumkeag for Winterlights

In this magical outdoor spectacle, see thousands of shimmering holiday lights throughout the Naumkeag property, from the public garden to the historic home. Embark on a self-guided tour and take in the 120,000 lights. Walk through enchanting LED tunnels, see trees twinkle with brilliant bulbs, and stare awestruck at fountains rippling green and red hues.

Browse the Berkshire Botanical Garden Holiday Marketplace

Calling all last-minute shoppers. The holiday market at the Berkshire Botanical Garden is the perfect place to find unique gifts for everyone on your list this year. View the legendary Gallery of Wreaths, plus purchase an assortment of blooming amaryllis and paperwhites. From decorative garlands to hanging terrariums, the plant lovers in your life will thank you! 

Visit Lenox Winterland

Visit Winterland in Lenox all month long. It starts with a tree lighting in Lilac Park on December 2, followed by a can't-miss photo op with Santa. Other seasonal events include a restaurant walk, where participants can try signature cocktails and small plates, an art show at the town's library, and a performance from The Cantilena Chamber Choir. 

Watch It's A Wonderful Life

You want the moon? Just say the word, and the Mahaiwe Performing Arts Center will give it to you! On December 22, join them for their annual screening of the holiday classic It's a Wonderful Life. A favorite feel-good film, it features the famous Jimmy Stewart, who learns lessons about family, friendship, and faith. 

Celebrate at The Red Lion Inn

After you embark on a merry and festive tour around Stockbridge, settle in at The Red Lion Inn. We have a packed itinerary of winter activities as part of our Joyful Family Holidays programming. 

Get cozy on our front porch with a cup of mulled apple cider or hot cocoa. Decorate a gingerbread house, try festive trivia, or let the timeless tunes of the harp soothe you by the fire. From brunch with St. Nick to 'Twas the Night Before Xmas Afternoon Tea, make your holiday memories here. The best of the Berkshires awaits—book your room now


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Where to Find the Best Christmas Lights Around Stockbridge, MA

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What to Do on a Weekend Getaway in Stockbridge, MA