Pittsfield Halloween & Things to Do 2026
Your complete guide to the best halloween in Pittsfield and surrounding areas
Pittsfield kicks off Halloween 2025 near the main district and historic Park Square with ghostly tours and frightful events throughout October.
Halloween offerings include Halloween adventures, autumn gatherings and supernatural fun featuring pumpkin carving, haunted walks and family-friendly festivals.
Find the best Pittsfield Halloween happenings this year!
Browse Halloween Near Pittsfield by Category
Family-Friendly Fall Activities
Two-day festival with parade and Imagine Park
Haunted Experiences
Bigger scares and more entertainment this fall
Movies, Theater, and Entertainment
All Shakespeare plays in under two hours
Food, Drink, and Parties
10th Annual Oktoberfest Massachusetts celebration
Unique & Unusual
Meet legendary horror icons and explore a world of terror.
Editor's Picks
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Nightmare Acres
(South Windsor)
Bigger scares and more entertainment this fall
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CT HorrorFest
(Hartford)
Meet legendary horror icons and explore a world of terror.
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DementedFX Haunted House
(Holyoke)
20,000 sq ft of giant monsters and immersive horror.
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MyKingstonKids Halloween Fest & Parade
(Kingston)
Two-day festival with parade and Imagine Park
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All-Hallow E'en Festival
(Albany)
Revival of historic 1904-1905 Halloween carnival
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Oktoberfest Massachusetts 2025
(Hadley)
10th Annual Oktoberfest Massachusetts celebration
Pittsfield Halloween Events Map
See every Halloween event, haunted attraction, and pumpkin patch on one map.
