The Berkshires Blog

Make the Berkshires Your Home Away From Home For The Holidays

By Kelly Bevan McIlquham

When you think of celebrating a quintessential New England holiday with your family what does it look like? Families strolling the picturesque streets of a small town, window-shopping at locally-owned shops for toys, sweets and unique gifts? Maybe that picture includes spending a day on the slopes or on a  local sledding hill, before winding down in front of a crackling fire with steaming cups of hot chocolate heaped with extra whipped cream for the kids. Or perhaps, your vision is more like the images depicted in Norman Rockwell’s famed “Stockbridge Main Street at Christmas” painting. Children running through the streets while parents’ arms overflow with packages, neighbors stopping to chat and catch up, or simply waving a friendly hello to anyone who passes and carolers going door-to-door spreading holiday cheer.

Believe it or not, not much has changed during the holiday season in the Berkshires since that scene was captured on Rockwell’s canvas for McCall’s Magazine in December of 1967. Families who decide to make the region their home away from home during this festive season can experience all of the above … and then some, as the locals prepare for the holidays this year.

Tree lightings kick off the season as early as Nov. 26 (North Adams), as well as annual holiday staples like the Great Barrington Rudolf Steiner School’s 42nd annual Holiday Handcraft Fair on Nov. 15 and “Christmas at the Colonial with Mary Verdi” set for Nov. 29. More trees will be lit at annual events such as the Festival of Trees at the Berkshire and Bennington Museums (beginning Dec. 1), the Holiday Walk in Williamstown and Light Up the Holidays in Dalton (Dec. 6) and the Stockbridge Main Street at Christmas weekend-long celebration featuring holiday concerts and activities, local house tours, children’s story times, caroling, luminary walks and more. It all concludes on Dec. 7 with a reenactment of the original scene depicted in Rockwell’s painting complete with vintage automobiles parked in the exact same spots as in the painting.

Holiday concerts and performances like the Close Encounters with Music: A Holiday Celebration (Dec. 6) and John Pizarelli  and Jane Monheit (Dec. 27) at the Mahaiwe Performing Arts Center; “The Nutcracker” (Dec. 6 and 7) and “A Christmas Carol” (Dec. 14-22) at the Colonial and “It’s A Wonderful Life: A Live Radio Play” at Shakespeare & Company (Dec. 5-28) also fill the calendars during the season.

Families celebrating Hanukkah might want to mark their calendars for the Dec. 21 Hanukkah Family Celebration at the Berkshire Mall in Lanesborough, featuring live music, face-painting, dancing, latkes, a giant menorah lighting and more. And usually around this time of year a local Hanukkah (and later Christmas) concert by local children’s performer David Grover is scheduled.

Want to soak up even more of that New England holiday spirit in the Berkshires? Try strolling the streets of downtown Great Barrington, Pittsfield, North Adams or Williamstown, window shopping (or really shopping) at family favorites such as Tom’s Toys, Robin’s Candy Store, Persnickety Toys or Imagine That!? The skiing and/or sledding at Catamount, Bousquet, Butternut, Berkshire East, and Jiminy Peak is a must, or families might really feel like the locals and experience some holiday sledding at a local hill in the area (see a list at Then head back to your home away from home for that fire and hot chocolate. Better yet, make a stop at Chocolate Springs for a mug of their signature Serious Hot Chocolate!

A Portland, Oregon visitor to the shop said this about the hot chocolate on Yelp. “Remember the river of chocolate (with the bright pink boats) in Charlie and the Chocolate Factory? The hot chocolate from Chocolate Springs is right out of that book: complex, deep flavor with every mouthful full of richness, as if the Oompa Loompas and the rush of the river had truly churned this cocoa to perfection.”

Seriously, it’s that good! While you’re there, there are plenty of treats for the stockings and packaged delectable for the sweet-tooths on your holiday shopping list.

I could go on and on about the events and activities that will make the Berkshires the perfect home away from home for your holidays this year, but instead I’m just going to direct you to the Visitor Bureau’s events calendar or the Family Calendars at Berkshire Family Focus. You will find all you need to feel like you’re home for the holidays.


Kelly Bevan McIlquham was born and raised in Berkshire County, and is now raising her three children, with her husband in Hinsdale. She is the founder of Berkshire Family Focus, an online source for family activities, events and more in the Berkshires.