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Festival of Trees: Barn to Be Wild

Hancock Shaker Village 1843 West Housatonic Street, Pittsfield, MA
$20

Berkshire Museum and Hancock Shaker Village are excited to announce a unique collaboration for the 2025 Festival of Trees program, entitled Festival of Trees: Barn to be Wild! This annual festive tradition typically sees Berkshire Museum hosting dozens of trees decorated by local organizations, businesses, and individuals, all inspired by that year's theme. This year, […]

Arts and Culture, Exhibits, Family Friendly, Holidays

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  • Downtown Pittsfield Festive Frolic

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

    Downtown Pittsfield, Inc. is excited to bring back the Festive Frolic on Friday, December 5 and Saturday, December 6. Activities on Friday include the City of Pittsfield’s Park Square Tree Lighting Ceremony at 6 pm. Saturday’s events include The Berkshire Bazaar hosted by Thistle ‘n Thorn Floral at The Holiday Inn from 11 am to […]

    Festivals, Holidays

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  • Clark Art and Williamstown’s Holiday Walk Weekend

    Downtown Williamstown Spring Street and Water StreetWilliamstown,

    The Clark Art Institute joins in the community-wide celebration of the holidays during Williamstown’s 42nd Annual Holiday Walk Weekend. Friday 12/05 On December 5, Jenny Herzog kicks off the season in style with a spirited concert blending the Great American Songbook, tap dance, and holiday classics. Herzog—a part-time Berkshire County resident—celebrates the long relationship between […]

    Family Friendly, Festivals, Holidays, Outdoor Event

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  • Home for the Holidays with Norman Rockwell

    Norman Rockwell Museum 9 Route 183, Stockbridge, MA

    This heartwarming collection of holiday themed works by Norman Rockwell—from Thanksgiving and Christmas to New Year’s—are showcased in this lively installation of enduring seasonal favorites. Renowned for his ability to capture the spirit of American life, Rockwell’s paintings reflect the joy and nostalgia of the season as inspired by classic tales, holiday festivities and greetings, […]

    Exhibits, Family Friendly, Holidays

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  • Williamstown Holiday Walk

    Downtown Williamstown Spring Street and Water StreetWilliamstown,

    Are you ready for the 42nd Annual Williamstown Holiday Walk??!! Check the link for the complete list of events, including concerts, the ReinDog parade, tree decorating, tree lighting, breakfast with Santa, and more! Take your photo at the Hatchlings art installation on the Williams President’s House Lawn all weekend.

    Family Friendly, Festivals, Holidays, Outdoor Event

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  • Holiday Marketplace and Gallery of Wreaths

    Holiday Marketplace and Gallery of Wreaths

    Berkshire Botanical Garden 5 West Stockbridge Road, Stockbridge, MA

    An eagerly awaited tradition continues at Berkshire Botanical Garden, with Holiday Marketplace featuring the legendary Gallery of Wreaths. The festivities begin Friday evening with the Holiday Wreath Preview Party. The party includes early wreath-buying opportunities, live music, hors d’oeuvres, libations, and merriment! The Holiday Marketplace runs Saturday and Sunday. Select from a collection of 100 […]

    Belong Berkshires, Family Friendly, Festivals, Holidays

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  • Nightwood

    Nightwood

    The Mount, Edith Wharton's Home 2 Plunkett Street, Lenox, MA
    Free – $30

    The Mount, Edith Wharton’s Home is thrilled to announce the return of the popular winter sound and light show, NightWood, November 21, 2025 – January 3, 2026. Now in its sixth season, NightWood invites visitors to step into a fantastical landscape where music, light, and nature come together in a journey under the stars. This […]

    Family Friendly, Holidays, Outdoor Event

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  • FriYAY Karaoke

    FriYAY Karaoke

    Dalton American Legion 258 North Street, Dalton, MA

    This FRIDAY and EVERY Friday is Karaoke Night at the Dalton American Legion.The crowd is fun and supportive. Come on out and give it a try.We are proud of the volunteers that run these Karaoke nights, please come show them your support.SUPPORT YOUR LOCAL AMERICAN LEGION POST!Thank You Chief, Marie & Dan!!#intheberkshires

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