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  • Pittsfield (Indoor) Farmers Market

    Featured Pittsfield (Indoor) Farmers Market
    Zion Lutheran Church 74 1st Street, Pittsfield, MA, United States

    Come celebrate our Indoor Market season! You’ll find everything you need—fresh local produce, eggs, meats, and mushrooms; delicious baked goods and breads; hot coffee and Mediterranean food; treats for you […]

  • A Christmas Story for $1

    Featured A Christmas Story for $1
    The Beacon Cinema 57 North Street, Pittsfield, MA

    Celebrate the season with a timeless classic! A Christmas Story returns to the big screen at Phoenix Theatres for just $1 a ticket. Bring the whole family and enjoy the […]

  • Holiday Shindy

    Featured
    Masonic Temple 116 South Street, Pittsfield, United States

    On Saturday, December 13th 2025, a Berkshire benchmark of spectacular sustainable craft tradition will again take place in Pittsfield’s Upstreet Cultural District. For 18 years the Holiday Shindy has been […]

  • Festival of Trees

    Featured Festival of Trees
    Hancock Shaker Village 1843 West Housatonic St., Pittsfield, MA, United States

    Berkshire Museum’s popular winter exhibition comes to the historic grounds of Hancock Shaker Village, with Festival of Trees: Barn To Be Wild! Come explore the Village as you gaze upon beautifully […]

    Free – $20

  • DJ on the Deck

    Featured
    Bousquet Mountain 101 Dan Fox Drive, Pittsfield, MA, United States

    Get ready to turn up the heat on the slopes! Whether you’re carving fresh runs all day or just here for the vibes, DJ on the Deck is your Saturday […]

  • Crafting with Rainbow Seniors

    Featured Crafting with Rainbow Seniors
    WANDER Berkshires 34 Depot Street, Pittsfield, MA, United States

    🧶 Come Get Your Craft On at WANDER! 🎨 Crafting with Rainbow Seniors Second Saturday of every month 🕧 12:30–2:00 PM Calling all knitters, crocheters, doodlers, makers, and creatives of […]

  • Holiday Open Studios

    Featured
    Clock Tower Artists 75 South Church Street, 3 Floor, Pittsfield, United States

    Ready to find the perfect holiday gift — and maybe even surprise yourself with something magical? Join us for a festive Holiday Open Studios with the Clock Tower Artists! The […]

    Free

  • Eagles Band Holiday Concert

    Featured
    First United Methodist Church 21 Pearl Street, Pittsfield, MA, United States

    Free Holiday Concert with your favorite tunes of the season.Intermission bake sale and a prize giveaway!