Chatham OctoberFeast 2025 was held Saturday, October 4, 11:00am-4:00pm

This free event attracted visitors from around the region, as well as local residents, to enjoy family-friendly activities in the heart of Chatham: food and drink, magic show, live bands, entertainment, carved pumpkin contest, dog costume contest and parade, pumpkin decorating & other kids’ activities.

11:00am-11:45	Emacs performs fiddle music from beyond. Presented by PS21: Center for Contemporary Performance	Main Stage
11:00am-Noon	Violin /accordion music	Clock Tower
11:00am-4:00pm	Stonykill DJ spinning records	Main Street
Noon-1:00pm	Ragamufins pop up entertainment	Main Street
12:15-2:30pm	Love Button (classic rock From Brooklyn)	Main Stage
1:00-3:00pm	Scott Stockman Music	Clock Tower
3:00-5:00pm	Bits & Pieces, local favorite ’70s, ’80s, ’90s	Main Lot
7:00-9:00pm	Hot Shot Hillbillies. Berkshire’s Best Band- rockabilly – presented by Chatham Brewing	Main Lot
7:00-9:00pm	Big Frank & The Bargain Bingers, Honkey Tonk Blues Band	People’s Pub, 36 Main Street

11:00am-Noon	Sign up Dog Costume Parade	Main Lot
12:15pm	Dog Parade line up	Main Lot
12:30pm	Dog Parade kick off	Main Street
12:45-1:15pm	Dog costume judging	Clock Tower
1:15pm	Dog costume winners announced	Clock Tower

Sponsored by Johnnie Walker Insurance

11:00am-Noon	Drop off Carved Pumpkins	Main Lot
Noon-12:30pm	Pumpkin judging	Main Lot
1:00pm	Pumpkin winners announced	Main Lot
7:00pm	Lighting of the Pumpkins	Main Lot

11:00am-1:00pm	Ooms goats presented by Bimi’s Cheese	Gazebo
1:30-3:30pm	Magic show, face painting and balloon tying	Gazebo
11:00am-4:00pm	Haywagon rides	Pick up on Park Row
11:00am-4:00pm	Kids pumpkin decorating	Gazebo
11:00am-4:00pm	Kids activities at the Morris	Park Row
11:00am-4:00pm	Cider pressing – presented by Johnny Walker Insurance	Gazebo
Noon-5:00pm	Wine and cheese tasting	Chatham Wine & Liquor, 53 Main Street
1:30-2:00pm	Group Yoga – presented by Chatham Yoga	Main Street