A Time to Celebrate

Holiday Dining & Events in the Berkshires

The holiday season is upon us, and so is crisp, new-fallen snow, blue skies, and the rush of cool mountain air. Ahhhh – it’s winter in the Berkshires, and time for holiday celebrations with friends, family, or just that special someone!! Ready for that ski trail, a little tubing, a visit to a one-of-a kind museum or concert, or a day of shopping and sweet treats? Need to fuel that visit, perhaps by enjoying a sumptuous meal beside a warm fire where you can listen to live jazz? Keep reading to find cheery ideas to fill your Hanukkah, Christmas, or New Year’s plans. 

Holiday Dining

12 Days to Celebrate the Holidays at The Barn at The Williams Inn

From December 13-24, The Barn will feature a daily holiday dish or special,  including a movie night dinner and a night of charitable giving. Check the website for complete details.

“Joyful Family Holidays” at The Red Lion Inn

The Red Lion Inn is offering daily holiday celebrations in conjunction with The Norman Rockwell Museum, including a Santa Brunch and gingerbread house decorating. Dine on Christmas dinner amid old fashioned decor and ambiance. 

Christmas Eve To-Go at Mazzeo’s Ristorante

Always a wonderful place to enjoy a delicious meal, Mazzeo’s is open on Christmas Eve with a take-out only menu, including a selection of festive cocktails. Yum!

Festive Events

Nightwood at The Mount

Through January 1, 2023 – The Mount, Edith Wharton’s historic Lenox home, is excited to present its third year of NightWood, an innovative sound and light experience that immerses visitors in a fantastical winter landscape.

Naumkeag’s Winterlights

Through January 7, 2023 – Naumkeag will sparkle with thousands of shimmering, artfully designed holiday lights. Bring the whole family for a magical and fun outdoor experience they will remember forever— with food, refreshments, and more.

Berkshire Museum’s Winter Festival: Solstice Celebration 

Through January 8, 2023 – Winter Festival exhibitions include Santa Classics, where visitors get to see Kris Kringle in their favorite classical works of art. Learn about Hoot’s Holiday: A Solstice Tale, written by Berkshire Museum’s Exhibitions Research and Content Editor Charlie Catacalos. Hoot’s Holiday follows a journey through time with an Owl living atop the roof of Berkshire Museum as they find objects historic to the Berkshires. 

Hancock Holiday Nights

December 1-31, 2022 – With historic Shaker buildings adorned in lights, stroll through Hancock Shaker Village’s 19th century living history museum bedecked for the holidays, followed by cocktails at the firepit.

Stockbridge Main Street at Christmas

December 3-4, 2022 – See Stockbridge in all its quintessential holiday glory! Advance tickets are needed for weekend events. Visit during the rest of December for the lights and ambiance.

Mistletoe and Music with Berkshire Scenic Railway

December 3, 10, and 17, 2022 – Take an afternoon or early evening holiday-themed train ride and enjoy cabaret style music. BYOB and snacks.

Tinseliner Trains with Santa Claus

December 3, 4, 10, 11, 17, and 18, 2022 – Ride the rails with Santa on the weekends in December on the Berkshire Scenic Railway. Check the website for times and tickets.

Berkshire Grown Winter Markets

December 17, 2022 – Housy Dome in Great Barrington

December 18, 2022 – Greylock Works in North Adams

Deck your holiday tables with an abundance of locally sourced and produced foods, and meet our local farmers.

New Year’s Eve with Whiskey City at the Colonial Theatre

December 31, 2022 – Join The Colonial Theatre for a very special performance by Berkshire County’s Favorite Country-Rock Band, Whiskey City, along with special guests Lindsay Anne and the Hotshot Hillbillies! Check out the Colonial’s calendar for additional holiday shows in December.

You can find more holiday inspiration here. Continue exploring things to do, places to stay, and where to eat and drink and be merry! Check our online calendar frequently for myriad events.

Photo Credits: Tinseliner Train, Hoosac Valley Train Ride; Winterlights, Naumkeag

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