2025 Holiday Season Art and Events Guide
A selection of the season's most exciting events.
As Autumn’s extravagant hues fade to brown and the winds grow colder, the Hudson Valley, Berkshires, and Litchfield hills begin to transition from displays of harvest spirit for a bounty of holiday seasonal to-dos. From the Day of the Dead to festivals of light, November and December are replete with uplifting events to ward off the doldrums. But it’s not just homages to the religious and pagan festivals of old, created to keep people from going stir crazy while the sun hides for most of the day. Local arts venues continue to arouse our patronage with delightful performances and exhibitions. Seasonal Affective Disorder be damned!
Holiday Festivals and Events
NightWood: An Enchanted Sound & Light Walk at The Mount
Select evenings November through January, Lenox, MA
NightWood turns the gardens of Edith Wharton’s estate into a nocturnal narrative of light and sound. Guests follow a winding outdoor trail through forested paths, encountering seven immersive vignettes blending nature, myth, and seasonal motifs. Each station pairs subtle lighting effects with original sound design to create dreamlike landscapes. Between walks, the NightWood Cafe, in the mansion courtyard, offers hot cider, cocoa, and sweet treats, while the museum shop stays open for holiday purchases.
Basilica Farm & Flea Holiday Market
November 28-30, Hudson
Basilica Hudson becomes a holiday marketplace focused on local craftsmanship at Farm & Flea’s winter edition. Conceived as a rejection of the capitalistic chaos of Black Friday, over the Thanksgiving weekend, more than 120 local vendors converge under the former factory’s high ceilings. Craft makers, vintage dealers, farmers, and artisans all take part in the highly social shopping extravaganza. The vibe is carefully curated to present only local, ethical, handcrafted producers. There’s also artisanal food including wood-fired pizza, waffles, mulled cider, and small-batch sweets. Expect a mix of browsing, community, and grunge-chic.
Winterlights at Naumkeag
November 28–January 3(Wednesday–Sunday evenings), Naumkeag, 5 Prospect Hill Road, Stockbridge, MA
Each winter, the gardens of Naumkeag transform into a holiday spectacle in Winterlights, where thousands of twinkling lights trace pathways, terraces, and gardens, creating shimmering landscapes after dark. This season’s display runs Wednesday through Sunday evenings, beginning the Friday after Thanksgiving and concluding the first weekend of January. Timed-entry tickets (purchased in advance) guide visitors through illuminated scenes—some classic, some new—with shuttles from downtown Stockbridge to shuttle zones and various parking options. Highlights include glowing arches, light sculptures among evergreens, and choreographed light moments that surprise as you round each bend. Note: the terrain is steep and uneven, so sturdy footwear is recommended and accessibility is limited.
Kent Gingerbread Festival
December 1-31, Thursdays through Sundays, Kent, CT
The sweetest holiday tradition in Kent returns as downtown shops fill with the spicy aroma of gingerbread. Now in its 13th year, the Kent Gingerbread Festival showcases imaginative gingerbread houses crafted by local bakers and artists. Delightful creations are tucked into 23 participating businesses around town. Pick up a map and embark on a gingerbread scavenger hunt: Collect clues at each display to solve a festive riddle, then turn in your answer to claim a prize. Don’t forget to vote for your favorite sugary structure to crown the People’s Choice winner. Displays are open Thursday through Sunday all month, making this a leisurely self-guided tour of Kent’s shops. Fun, free, and utterly charming, it’s a must-do celebration of community creativity and holiday cheer.
Bethlehem Christmas Town Festival
December 5-6, Bethlehem, CT
Bethlehem transforms into its namesake Christmas Town for this 44th annual festival, a beloved tradition that ushers in the holidays. Festivities kick off as Santa himself helps light the town Christmas tree. All weekend, the village green and Main Street fill with old-fashioned cheer: local vendors selling gifts, horse-drawn hayrides, an illuminated fire-truck parade, live music and dance performances, and a morning “Santa Made Me Do it” 5K. Children can hang out with Santa for a photo, make free crafts, and join scavenger hunts. Seasonal food and drink options will surround you and make themselves inevitable.
Great Barrington Holiday Market
December 6-7, Great Barrington, MA
Great Barrington’s storefronts, galleries, and pop-up tents unite for this weekend-long holiday market of local artisans. In every corner, you’ll find ceramics, textiles, candles, small-batch foods, woven goods, and one-of-a-kind seasonal gifts. Shop window displays burst with lights and color, musicians drift among crowds, and performance artists surprise you at unexpected corners. Pausing for a cup of cider or sweets, you soak in the seasonal energy of town and craftspeople in sync.
Hudson Winter Walk
December 6, Hudson
Hudson’s Winter Walk envelops Warren Street in holiday glow, happy crowds, and music. Strolling along, you’ll find bands, circus performers, dancers, choruses, costumed characters, fireworks, street food vendors, petting zoos, horse and carriage rides, holiday lights and decorations, and signature late-night shopping. It’s a full-town, multi-site celebration designed to marry winter’s chill with community warmth.
Stockbridge Main Street Christmas
December 6-7, Stockbridge, MA
Stockbridge will be adorned with twinkling lights and charming holiday wreaths that evoke the spirit of the season, offering a delightful array of family-friendly activities. From live performances and historic property tours to bustling holiday markets and the Winterlights display, there’s much to do. Don’t miss the Rockwell Holidays at the Museum, where art and tradition come alive, or the the shops and restaurants that showcase the best the town has to offer. And of course, Santa himself will be making appearances.
Kent Holiday Fest
December 6, 3-7pm, Kent, CT
Kent’s Holiday Fest invites towns across Litchfield County to converge on the town green for an afternoon and evening of seasonal magic. Local artisans vend crafts in tents and musicians take turns on stage. Children may ride horse-drawn wagons, join in cookie decorating, or sing karaoke. As dusk falls, the town tree is lit amid cheers and carols, and the celebration spills into neighboring storefronts, which often stay open late for holiday browsing.
Canaan Holiday House Tour
December 5-6, various private homes, Canaan/Falls Village, CT
This annual house tour opens historic homes, barns, and inns across the Canaan region. Guides take visitors through gorgeously decorated interiors—a mix of folk, Colonial, and modern holiday styles—while lobbies serve complimentary cider, cookies, and music. Because many houses are private residences, tickets are limited and advance reservation is encouraged.
Festive Performance
“Pippin” at the Copake Grange
November 7-9 and 14-16, Copake Grange, Copake
In a committed community production, The Two of Us Productions presents “Pippin” at the historic Copake Grange over two weekends. The show follows young Pippin—heir to the Frankish throne—as he quests through war, romance, political intrigue, and illusion in search of true happiness. Under the guidance of a mysterious troupe of players, he comes to realize the deeper beauty hidden in ordinary life. Expect soaring musical numbers like “Corner of the Sky” and “Magic to Do.” Friday and Saturday shows begin at 7:30pm, Sundays at 3pm.
Vocal Fireworks: LIVE @AMP — A Cappella Showcase
Nov 15, doors 7:00 pm / show 8:00 pm, American Mural Project, Winsted, CT
The American Mural Project’s Live @AMP series returns with Vocal Fireworks, an energetic a cappella concert featuring three standout collegiate groups: Brandeis University’s Starving Artists, UConn’s Extreme Measures, and Wesleyan’s Notably Sharp. Held inside AMP’s soaring five-story mural gallery, the evening marries rich vocal harmony with immersive architecture. Each group offers its own repertoire of modern, jazz, and classic tunes before uniting in a blowout finale that blends voices in soaring crescendos.
“A Christmas Story” at the Center for Performing Arts at Rhinebeck
December 5-21, Rhinebeck
This adaptation of the beloved movie A Christmas Story brings Ralphie Parker’s holiday adventures to the stage in full nostalgic glory. Set in 1940s Indiana, the show features every iconic moment—“you’ll shoot your eye out,” the leg lamp, the pink bunny suit—all performed live with comedic timing and heart. The ensemble cast (kids and adults) brings humor and warmth to family antics, with the narrator guiding audiences back into childhood memory. Performances run weekends and a few matinees, making it a festive outing for all ages.
Stella Cole at Studio E at Tanglewood
December 13, 7pm, Lenox, MA
Vocalist Stella Cole brings her classic tone and deep reverence for the Great American Songbook to Tanglewood’s holiday season. As part of the Tanglewood Learning Institute’s winter series, this performance leans into seasonal standards, all delivered with her soulful clarity and stylistic playfulness. Audiences can expect a blend of jazz, cabaret, and nostalgic charm. The show is part concert, part celebration, part invitation to reflect on the staying power of the standards.
