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Stockbridge: Main Street at Christmas

Stockbridge Chamber of Commerce 50 Main Street, Stockbridge, MA

The town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas. Sponsored by the Stockbridge Chamber of Commerce, the holiday celebration offers a full range of holiday activities […]

Arts and Culture, Family Friendly, Festivals, Holidays


The Polar Express

Phoenix Theatres Beacon Cinema 57 North Street, Pittsfield, MA

Join Phoenix Theatres for a special screening of The Polar Express during the first week of December, with tickets priced at just one dollar! Bring your family and friends for an enchanting cinematic experience that captures the true spirit of the holiday season. Tickets sell fast, so make sure to get yours ahead of time! See […]

Holidays, Performing Arts & Entertainment



The Mount, Edith Wharton's Home 2 Plunkett Street, Lenox, MA
Free – $25

NightWood is back! Join us for another innovative and immersive sound and light experience set against the backdrop of Edith Wharton’s historic home. Wander the illuminated 3/4-mile route through the woods and gardens for a fantastical journey that evokes wonder and awakens the imagination. Don’t miss the four new encounters this year!

Arts and Culture, Family Friendly, Holidays, Outdoor Event


Holiday Downtown Pittsfield Passport

Downtown Pittsfield, Inc. 33 Dunham Mall, Suite 102, Pittsfield, MA

Downtown Pittsfield, Inc. (DPI) will be facilitating a Holiday Downtown Pittsfield Passport giving shoppers a chance to win one of three prize packages made up of donations from the 40 participating local businesses. The grand prize value will be over $500. The promotion will run Friday, November 24 through Sunday, December 3 and will encompass Black Friday, […]

Family Friendly, Holidays


Festival of Trees: Nostalgia

Berkshire Museum 39 South Street, Pittsfield, MA
Free – $15

This installment of the decades-old community tradition offers participants the opportunity to celebrate the long history and deep roots of community in the Berkshires while capturing the essence of our institutions, schools, and businesses. The theme of “Nostalgia” complements Berkshire Museum’s three-part 120-year anniversary exhibition series exploring the history of the Museum since its inception […]

Arts and Culture, Family Friendly, Festivals, Holidays

Holiday Craft Fair at Simon’s Rock

Bard College at Simon's Rock 84 Alford Road, Great Barrington, MA

The Employee Enrichment Activities Committee (EEAC) at Simon’s Rock will host their Annual Simon's Rock Arts and Craft Fair  in the Daniel Arts Center on campus. The Craft Fair will feature arts and crafts for sale from Simon’s Rock students, faculty, and staff. This festive fair is an excellent opportunity to get to know the […]

Family Friendly, Holidays


Winterlights at Naumkeag

Naumkeag House & Gardens 5 Prospect Hill Road, Stockbridge, MA
$7 – $30

Winterlights is back! Join us for a magical outdoor experience at Naumkeag as it sparkles with thousands of shimmering and artfully designed holiday lights. Bring the whole family for a fun and safe outdoor experience. Winterlights runs Wednesday through Sunday each week from the Friday after Thanksgiving through the first weekend in January.

Arts and Culture, Family Friendly, Holidays, Outdoor Event


Berkshire Potters Collective: First Annual Holiday Pottery Sale

Berkshire Art Center 13 Willard Hill Road, Stockbridge, MA

The Berkshire Potters Collective (BPC) presents its first annual Holiday Pottery Sale at Berkshire Art Center. An opening reception of the sale will take place on Friday, December 1st, from 5pm to 7pm at Berkshire Art Center’s flagship location, Citizens’ Hall. For purchases made during the event, 70% of sales will support the artists and 30% […]

Arts and Culture, Holidays

Festive Frolic: Wreath Art Auction

The Lichtenstein Center for the Arts 28 Renne Ave, Pittsfield, MA

Join Pittsfield’s Office of Cultural Development and dozens of local artists for the 8th Annual Wreath Art Auction. Talented local artists have graciously donated their time and talent to create beautiful holiday wreaths, centerpieces, kissing balls, and more! Grab and go wreaths will be available starting at 5 pm, and the top items will be […]

Arts and Culture, Family Friendly, Holidays