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Stockbridge Main Street at Christmas

Downtown Stockbridge

Rediscover the joys of the holidays in Stockbridge, MA, where the town transforms into a magical New England village, adorned with twinkling lights and charming holiday wreaths that evoke the spirit of the season. This enchanting destination offers a delightful array of family-friendly activities that promise to create cherished memories for all. From captivating live […]

Arts and Culture, Belong Berkshires, Family Friendly, Holidays

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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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  • The Mount: Weekend House Tours

    The Mount, Edith Wharton's Home 2 Plunkett Street, Lenox, MA

    Join us for a weekend house tour - available weekends now through December! If  you’re looking for the perfect weekend outing as we transition into winter, a tour of The Mount is a must! You’ll explore rooms filled with history, learn about Wharton’s fascinating life, and see why her home remains one of the most […]

    Arts and Culture, Exhibits, Family Friendly, History and Heritage

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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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  • Clark Art: First Sunday Free

    Clark Art Institute 225 South Street, Williamstown, MA

    The Clark Art Institute continues its First Sunday Free series. In celebration of Hugh Hayden's sculpture, the End, December’s First Sunday Free theme is Beasts and Bones. Enjoy free museum admission from 10 am–5 pm and take part in free special activities from 1–4 pm.

    Arts and Culture, Exhibits, Family Friendly

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  • Talks, Tea, and Toddies Author Series

    Talks, Tea, and Toddies Author Series

    Berkshire County Historical Society at Arrowhead 780 Holmes Road, Pittsfield, MA
    $75

    Beginning November 9, the Berkshire County Historical Society will host a special series of fund-raising readings featuring four authors with strong ties to the Berkshires. They take place in Herman Melville’s historic study where he wrote Moby-Dick inspired by his view of Mount Greylock. Following the readings, guests can interact with the authors while enjoying […]

    Benefits and Galas, Literature, Lectures, and Talks

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  • Tantalizing Talks with Tea & Toddies

    Tantalizing Talks with Tea & Toddies

    Berkshire County Historical Society at Arrowhead 780 Holmes Road, Pittsfield, MA
    $35 – $75

    Step into the warmth of history and storytelling as one of Berkshire County's talented writers reads aloud in Herman Melville's own study. Then, gather in the downstairs parlor for an intimate tea featuring decadent treats and a touch of winter magic. Choose from 4 different Sundays in November and December with 4 different authors. Tickets […]

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