The Berkshires Blog

Winter Festivities in the Berkshires Create Family Traditions

By Kelly Bevan McIlquham

November and December are brimming with tradition in the region. From Black Friday shopping at locations like the Berkshire Mall and Lee Premium Outlets and pick-up football games, to concerts, plays and holiday marketplaces, there are myriad activities in Berkshire County geared towards local and visiting families alike, that make it an ideal destination for beginning new family tradition or carrying on with traditions of old.

Once the turkey and “fixin’s” have been eaten and families can barely move, I’d encourage everyone to roll on over to the Colonial Theatre in Pittsfield where tradition abounds with family favorites such as  “Mary Verdi’s Christmas at the Colonial” set for Thanksgiving weekend this year (Nov. 30 and Dec. 1), the Albany Berkshire Ballet’s “The Nutcracker”  (Dec. 7 and 8) with dancers from the local community and Berkshire Theatre Group’s annual community production of “A Christmas Carol” running from Dec. 14-29.

“In 2006, we introduced Berkshire audiences to our production of ‘A Christmas Carol’ at our Unicorn Theatre. The production instantly became an annual favorite,” said BTG’s Artistic Director and CEO, Kate Maguire. “In 2011, we moved to The Colonial Theatre where ‘A Christmas Carol’ has found a wonderful new home. The Colonial is a perfect setting for this timeless tale about goodness and greed at this most treasured time of year.”

In past years Shakespeare & Co. in Lenox has provided the perfect backdrop for family tradition with its annual production of David Sedaris’ “The Santaland Diaries” on its Elayne P. Bernstein Stage. This year the company is breaking from tradition a bit by replacing the aforementioned play with “It’s a Wonderful Life: A Live Radio Show” running Dec. 6-9.

“I wanted a play this time that was perfect for the whole family. This touching and hopeful story will remind you of the strength and spirit of our beliefs and how much family and friends truly mean in our lives,” said Shakespeare & Company’s Artistic Director Tony Simotes. “I am very excited to be offering a true American classic that celebrates one of the best, if not most, inspiring stories of the season. I am hoping to create a new tradition of family entertainment here in the Berkshires. I hope that we can bring back ‘It’s a Wonderful Life’ year after year just as we did with our much loved ‘The Santaland Diaries.’“

Sitting in a warm theater during these cooler weather months may sound appealing, but mom-of-two, Erin Sullivan, and her family revel in their annual Christmas Eve tradition — strolling and caroling around their Pittsfield neighborhood.

“On Christmas night we walk from house to house in our neighborhood singing Christmas carols and sharing the holiday with our neighborhood family. It is a wonderful way to end the day, and even as kids have become adults they still look forward to our neighborhood stroll,” Sullivan said of her family’s annual tradition.

But you don’t have to live in a local neighborhood to partake in a neighborhood holiday-themed stroll such as Sullivan’s. In the spirit of neighborhood strolls everywhere, towns throughout the Berkshires continue to organize annual festivities at which families can walk the streets of the town, marvel at the various light displays, visit with community members over good food and hot chocolate, listen to music, partake in a holiday craft or two and more.

“After 17 years of doing ‘Light up the Holidays’ we are now in the next generation of families having kids,” said John Kelly, one of Dalton’s Light Up the Holidays family stroll organizers. “So now families look at this weekend as ‘I have to still come home and celebrate this. So adults who came to this as kids themselves are still coming ‘home’ (to Dalton) with their children for this weekend each year.”

An added bonus, Kelly said, “Families are coming home for this weekend and then returning for Christmas, so essentially families are getting two Christmases out of this.”

Dalton’s Light Up the Holidays celebration is set for Dec. 7, along with other walks such as the Williamstown Holiday Walk festivities (set for Dec. 6 and featuring a Reindog Parade, Christmas Tree Showcase, music and more); the Great Barrington’s Holiday Stroll (also on Dec. 7); and Stockbridge’s Main Street at Christmas (running for three days Dec. 6-8 with “Readings Around the Hearth,” Holiday House tours, a holiday luminaire walk and caroling and more.

Missed the traditional Black Friday shopping in the Berkshires? Have no fear. Annual holiday fairs and marketplaces provide the perfect opportunity to shop for the holidays, browse the wares of talented local artisans and bring a little bit of the Berkshires home with you. A few local favorites include Berkshire Botanical Garden’s Holiday Marketplace in Stockbridge (Dec. 7-8) and the Alchemy Initiatives Handmade Holiday Festival in Pittsfield also on Dec. 7.

And if none of the above suits your fancy be sure to check out the complete list of Holiday Events or create another family Berkshire tradition of your own — be it skiing or snowshoeing along the trails of a local mountain or simply sitting near next to a warm fire at a local restaurant sipping a steaming mug of hot cocoa. Whatever you choose, it will surely be something you and your children look forward to time and time again.


Kelly was born and raised in the Berkshires and is now living and raising her three children, Max, McKenna and Shea, and her husband Mark in Hinsdale. She is the founder of Berkshire Family Focus, the one-stop online source for family activities, events, information and more in Berkshire County.