The Downtown Pittsfield area will host a Halloween Paint & Sip activity. This event is organized by the Pittsfield Parks & Recreation Department and Foster MA/Adopt MA.
🎃 Halloween Paint
Pittsfield News & Updates
Stay informed about the latest events and activities in Pittsfield
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Latest: Saturday, October 17, 2026
Saturday, October 17, 2026
🎃 Halloween Ride
A Halloween Ride is scheduled for Saturday, October 31st, with departures starting at 1:30 p.m. This event is associated with the Pittsfield Parks & Recreation Department.
Friday, October 16, 2026
🎃 Halloween Activities
Downtown Pittsfield's It's Alive! Kids' Zone will provide free Halloween activities, games, crafts, and face painting. The event is scheduled to take place from 11 a.m. to 2 p.m.
🎃 Halloween Parade
The application deadline for the Pittsfield Halloween Parade has been extended. For inquiries, individuals can contact Jennifer VanBramer, Recreation & Special Events Coordinator, via phone or email.
Tuesday, October 13, 2026
🎃 Fall Festivals
The region is offering a variety of Halloween and fall attractions, with many events returning after contactless options were previously implemented. Hancock Shaker Village in Pittsfield, MA is one of the locations participating in these seasonal festivities.
Wednesday, September 30, 2026
🎃 Halloween Stores
Spirit Halloween stores are now open for the season across Massachusetts, with 34 locations available. A new Pittsfield location has opened at Lee Premium Outlets.