Cheshire Fall Festival 2026: Here’s What To Know

CHESHIRE, CT — The Cheshire Fall Festival will take place this weekend at Bartlem Park in Cheshire.

The celebration kicks off with “Food Truck Friday” on Friday, Sept. 18, including the Kiwanis Carnival and a concert, and continues Saturday, Sept. 19, with vendors on the Bartlem Park Great Lawn, followed by the annual fireworks show.

The food trucks will be in operation from 5 p.m. to 9 p.m. on Friday, and the band Women of Rock performs at 7 p.m. Adults can also enjoy Counter Weight Brewing Company beer and Lyman Orchards hard cider on Friday and Saturday night.

“On Friday, visitors can expect a variety of food trucks and entertainment throughout the evening,” reads a post on the Cheshire Fall Festival website. “Saturday, September 19th, promises to be a beautiful day filled with booths on display, food trucks, performances and demonstrations. Come walk the field and see what our local businesses, crafters, and vendors have to offer.

“In the evening, you will find musical performances on the main stage. Everyone will enjoy the Kiwanis carnival in the parking lot. Be sure to stop by our Cheshire Chamber of Commerce tent and introduce yourself. Come spend the weekend with us and see everything our town has to offer.”

On Saturday, more than 100 vendors and crafters will run from 10 a.m. to 4 p.m., and there will be food trucks and live music all day, with fireworks at 8 p.m.

The Re/MAX Rise Hot Air Balloon Rides will be held in front of Cheshire Pool from 9 a.m. to 11 a.m. There is a $20 suggested donation. Children under 12 must be accompanied by an adult.

For more information, including the entertainment schedule for Saturday, visit the Cheshire Fall Festival website here.