By Amy Krzanik
Photo above: Winterlights at Naumkeag, David Edgecomb
FESTIVE DECORATIONS AND EVENTS
NightWood at The Mount
Through January 3
Lenox | edithwharton.org
This immersive, otherworldly sound and light experience is set against the backdrop of Edith Wharton’s historic home.
Festival of Trees: Barn to be Wild
Through December 28
Hancock Shaker Village, Pittsfield
hancockshakervillage.org
berkshiremuseum.org
While the Berkshire Museum undergoes renovations, it will hold its beloved Festival of Trees exhibition at Hancock Shaker Village. All ages will enjoy decorated trees, each ornamented by a different Berkshires-based organization or business and designed around this year’s theme.
Berkshire Scenic Railway Holiday Train Rides
November 29–December 13
Adams Station, Adams
berkshiretrains.org
The historic Hoosac Valley Train Ride offers trips on the Tinseliner, featuring Christmas carols and a visit from Santa—and the Mrs. Claus Cookie Express, one time only, on December 20.
Winterlights at Naumkeag
November 28–January 3
Stockbridge
thetrustees.org/naumkeag
Naumkeag’s wildly popular Winterlights transforms the historic home’s expansive gardens into a twinkling fantasyland aglow with thousands of holiday lights.
Berkshire Theatre Group
December 4–31
Stockbridge & Pittsfield
berkshiretheatregroup.org
“A Christmas Carol” comes to Stockbridge’s Unicorn Theatre December 4–21, while Pittsfield’s Colonial Theatre hosts Holiday Jazz with Tim Jones, Mutts Gone Nuts, and concerts including New Year’s Eve with Max Creek.
Williamstown Holiday Walk
December 5–7
Downtown Williamstown
destinationwilliamstown.org
Williamstown rings in the season with caroling, carriage rides, a penny social, a ceremonial tree lighting, an appearance by Santa Claus, and the annual ReinDog Parade.
Stockbridge Main Street at Christmas
December 6–7
Downtown Stockbridge
stockbridgechamber.org
The picturesque town pays tribute to illustrator Norman Rockwell with a recreation of his painting, “Stockbridge Main Street at Christmas,” along with live music, holiday shops, and festive decor.
Ventfort Hall
Beginning December 12
Lenox | gildedage.org
The mansion welcomes guests for a Stockbridge Chamber Historic Holiday Property Tour on December 12, a Tea & Talk on Gilded Age Christmas Traditions on December 20, a Holiday Cabaret with Sherri James Buxton and Bob Shepherd on December, followed by a dessert tea, and two marionette shows by Carl Sprague on December 27 and 29.
Hudson Hall Winter Walk
December 6
Warren Street, Hudson, NY
winterwalkhudson.org
This annual tradition transforms a mile-long stretch of downtown into a festive wonderland with street performers, art installations, shopping, kids’ entertainment, food and drink, fireworks, and a visit from Santa.
Community Chanukah Dinner
December 19
Knesset Israel, Pittsfield
knessetisrael.org
Join friends for an energizing, musical Friday evening service, then stay for a kosher shabbat dinner. RSVP to save your spot.
Kwanzaa Celebration
December 20
Hudson, NY | hudsonhall.org
Operation Unite NY welcomes Kwanzaa with a free Umoja Community Celebration that includes kids’ activities, dancing, drumming, a candle-lighting ceremony, and more at Hudson Hall.
Winter Solstice Celebration
December 20
Olana, Hudson, NY | olana.org
Olana State Historic Site celebrates the beginning of winter with workshops, artmaking, seasonal storytelling, Hank the miniature donkey, and more.
Nightwood at The Mount, Eric Limon
HOLIDAY MARKETS
Basilica Farm & Flea
November 28–30
Basilica Hudson, Hudson, NY
basilicahudson.org
An antidote to big box Black Friday, this popular annual market features a large and diverse group of regional crafters and vendors alongside locally sourced, farm-fresh food.
Berkshire Botanical Garden Holiday Marketplace
December 5–7
Stockbridge
berkshirebotanical.org
The Gallery of Wreaths is the centerpiece of this annual market, but shoppers can also find seasonal plants, decorative containers, terrariums, and crafts from regional artisans.
Troutbeck’s Holiday Bazaar
December 6–7
Amenia, NY | @troutbeck.ny
This event celebrates small businesses with craftsmanship and creativity at the forefront, all presented with an eye toward understated luxury. Vendors include favorite shops, local artisans, jewelers, NYC-based boutique fashion lines, and toys galore.
Holiday Shindy
December 13
Masonic Temple, Pittsfield
holidayshindy.com
The popular Shindy returns in a new location with the same high-quality gifting options from regional artisans, farms, and makers.
Great Barrington Shop, Sip & Stroll
December 13
Downtown Great Barrington
southernberkshirechamber.com
The Stroll features dozens of free activities including crafts, games with prizes, encounters with holiday characters, and more throughout downtown Great Barrington.
Delightful & Delectable Holiday Market
December 20
Berkshire Food Co-op, Great Barrington | @gbartsmarket
Great Barrington Arts Market (GBAM) presents a unique holiday sale featuring the best of the Berkshires’ handmade gifts and delicious giftable treats.
Stockbridge Main Street at Christmas, Gillian Jones
ARTS AND MUSIC INTO THE NEW YEAR
Norman Rockwell Museum
Opening November 8
Stockbridge | nrm.org
“Jazz Age Illustration” and “Shine a Light: The Art and Life of Deb Koffman” open in early November and continue into 2026.
The Clark
Opening November 22
Williamstown | clarkart.edu
Two new shows—“Raffaella della Olga: Typescripts” and “Shadow Visionaries: French Artists Against the Current, 1840–70”—join a film series, live music performances, and more into the new year.
The Foundry
November 29
West Stockbridge
thefoundryws.com
Award-winning clarinetist and composer Itay Dayan and his Band will perform a night of klezmer music. The Boston-based, Israeli musician is considered one of today’s most promising voices in klezmer.
MASS MoCA
Opening December 6
North Adams | massmoca.org
In “RACE/HUSTLE,” Zora J Murff’s photographs invite viewers to examine how systems of domination interlock. Opening February 21, 2026, the group show “Technologies of Relation” examines how we relate to each other, to our devices, and to our future.
Sense and Sensibility: A Lively Costumed Reading
December 12–14
Shakespeare & Company, Lenox
shakespeare.org
Based on the novel by Jane Austen, this reading follows the three Dashwood sisters and their widowed mother as they are forced to leave the family estate in Sussex and move to a modest cottage.
The Mahaiwe
December 20
Great Barrington | mahaiwe.org
Grammy Award-winning producer and guitarist extraordinaire John Pizzarelli and his trio salute the legendary Tony Bennett, celebrating over 60 years of unparalleled artistry.
I/O Festival 2026: The Music of Now
January 16–18
Williamstown | williams.edu
This contemporary music fest features three days of performances at the Williams College ’62 Center and the Clark Art Museum.
NICE ICE!
Fourth Annual Berkshire Pond Hockey Classic
February 7 or (weather backup) 14
Benedict Pond, Great Barrington
berkshirepondhockeyclassic.com
Coming soon!
A new refrigerated 100×50 outdoor ice rink will open in Pittsfield this winter, offering free public skating and programming.
