Pittsfield Halloween Events 2026
Your guide to the best Halloween events in Pittsfield and nearby
Pittsfield kicks off Halloween 2026 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.
Editor's Picks
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Pittsfield Halloween Parade
Long-running annual parade celebrating 80 years with futuristic-themed community floats.
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Naumkeag Pumpkin Show
· Stockbridge
Over 1,500 illuminated jack-o'-lanterns on historic estate grounds
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13 Nights at Jiminy
· Hancock
Outdoor haunted attraction on a historic plantation.
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The Mount Ghost Tours
· Lenox
Ghost tours in Edith Wharton's historic home
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Hicks Family Farm Haunted Corn Maze
· Charlemont
Dual-experience corn maze: family-friendly by day, terrifying by night.
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All-Hallow E'en Festival
· Albany
Revival of historic 1904-1905 Halloween carnival
Events Happening Soon
Browse Halloween Near Pittsfield by Category
Family-Friendly Fall Activities
Family festival featuring free pumpkin carving, games, and trunk-or-treat.
Haunted Experiences
Includes five haunted attractions and a psychic sideshow at one location.
Halloween Food, Drink, and Parties
Multi-venue Halloween bar crawl featuring drink vouchers and an after-party.
Halloween Movies, Theater, and Entertainment
Halloween dance party with DJ Michael V and a costume contest.
Unique & Unusual Halloween Events
Long-running annual parade celebrating 80 years with futuristic-themed community floats.
Latest News & Updates
Stay informed about Halloween events and activities in Pittsfield
- Pittsfield Halloween Paint & Sip Activity Published: Sat, Oct 17, 2026
- Halloween Ride in Pittsfield Published: Sat, Oct 17, 2026
Pittsfield Halloween Events Map
See every Halloween event, haunted attraction, and pumpkin patch on one map.
