October in the Berkshires of western Massachusetts means jack-o'-lanterns, crisp nights, and small towns lighting up with spooky fun. Whether you’re with little goblins or looking for a grown-ups’ night out, here’s your guide to trick-or-treating in towns across the region—and a special highlight: the Masquerade Macabre at Ventfort Hall in Lenox.
👻 Town-by-Town Trick-or-Treat Highlights
Here are some towns where Halloween traditions are alive and well, with trick-or-treat hours, parades, or special events. (Times may shift, so double check local listings before heading out.)
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Great Barrington – 5:30 to 7:30 p.m.
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Lenox – Downtown trick-or-treat, with participating businesses; generally 5:30 to 7 p.m.
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Stockbridge – Trick-or-treat 5 to 7 p.m., plus Halloween Parade & Pumpkin Walk-About.
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West Stockbridge – 4:30 to 6:30 p.m.; Town Hall party afterward with a costume contest.
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Sheffield – Trunk-or-treat and neighborhood routes, usually 5 to 7:30 p.m.
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New Marlborough – 5 to 7:30 p.m.; quieter, more spread out, great for families.
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Williamstown – 5:30 to 7:30 p.m. in residential and business districts.
🎭 Masquerade Ball at Ventfort Hall in Lenox
If you're looking for something haunted and elegant, mark your calendar:
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Event: Masquerade Macabre at Ventfort Hall, Lenox
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When: October 25
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What to expect: A dark, theatrical masquerade ball in a Gilded Age mansion, with local artists, performances, and a dance under autumn shadows. (21+ event.)
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Why go: Soak up spooky grandeur in a place with history and atmosphere—perfect for those who want more than candy and costumes.
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Link for details: https://berkshires.org/events/ventfort-hall-masquerade-macabre/\
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🍎 Tips for a Berkshire Halloween
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Dress in layers: Expect chilly evenings, but houses might be warm.
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Many towns host parades, pumpkin walks, and craft tables alongside trick-or-treating.
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Stop by local farms for cider donuts and pumpkins to round out the night.
