This free event attracts 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.
Apply to be a vendor
Applications are open to all food and beverage vendors, as well as vendors who feature food and table-top related products such as vendors of spices, condiments, flowers and table-top items.
Deadline for applications is Sunday, September 20.
Vendor fee is $100 for a 12’x12′ space, if paid by 9/20/25. Late entries will be considered, but may not be accommodated as spaces are usually in high demand.
Featured Events
Contest Registration
11:00am-Noon Main Lot
Parade Line Up
12:15pm Main St.
Parade Kick-Off
12:30pm Main St.
Judging
12:30-1:00pm Main St.
Winners Announced
1:30pm Clocktower
Drop Off/Registration
11:00am-Noon Main Lot
Judging
Noon-12:30pm Main St.
Winners Announced
1:00pm Main Lot
Pumpkin Lighting
7:00pm Main Lot
Strolling Accordion
11:00am-Noon Main St.
Ragamuffins
Noon-1:00pm Main St.
Love Button
12:15-2:30pm Main Lot
Music
1:00-3:00pm Clocktower
Hot Shot Hillbillies
7:00-9:00pm Main Lot
Full Schedule of Events
| 11:00am-Noon | |
| Strolling Accordion | Main Street |
| 11:00am-4:00pm | |
| Haywagon Rides | Park Row |
| Stonykill DJ Records | Main Street |
| Axe Throwing | Main Lot |
| Pumpkin Decorating for Kids | Gazebo |
| Group Yoga | Main Street |
| Popup Entertainment | Main Street |
| Kids’ Activities | Park Row |
| Kids’ Painted Window Contest | Main Street |
| Cider Pressing | Main Lot |
| Noon-12:30pm | |
| Carved Pumpkin Contest Judging | Main Lot |
| Noon-1:00pm | |
| Ragamufins Pop Up Entertainment | Main Street |
| 12:15-2:30pm | |
| Love Button, Classic Rock from Brooklyn | Main Lot/Main Stage |
| 12:30pm | |
| Dog Costume Contest and Parade Kick-Off | Main Street |
| 12:30-1:30pm | |
| Dog Costume Contest Judging | Clocktower |
| 1:00pm | |
| Pumpkin Carving Contest Winners Announced | Main Lot |
| 1:00-3:00pm | |
| Music | Clocktower |
| 1:30pm | |
| Dog Costume Contest Winners Announced | Clocktower |
| 1:30-3:30pm | |
| Magic Show | Gazebo |
| 2:30pm | |
| Stein Hoist Contest | Main Lot |
| 3:00-5:00pm | |
| Bits & Pieces, Local Favorite with Music from the ’70s, ’80s and ’90s | Main Lot/Main Stage |
| 5:00pm | |
| Main Street Reopens | |
| 7:00pm | |
| Lighting of the Carved Pumpkins | Main Lot |
| 7:00-9:00pm | |
| Hot Shot Hillbillies, Voted Berkshire’s Best Band, Rockabilly | Main Lot/Main Stage |
Drop Offs, Sign Ups, Line Ups, Load Ins & Pack Ups
| 9:00-10:30am | ||||
| Vendor load in on Main Street | ||||
| 11:00am | ||||
| All vehicles must be off Main Street | ||||
| 11:00am-Noon | ||||
| Dog Costume Parade Sign Up in the Main Lot | ||||
| Drop Off Carved Pumpkins to the Main Lot | ||||
| 12:15pm | ||||
| Dog Costume Contest Parade Line Up at Main Lot | ||||
| 4:00pm | ||||
| Vendor pack up from Main Street |