Cheshire Fall Festival 2026

Friday September 18th, 2025 – Food Trucks and Music
Saturday September 19th, 2025 – Cheshire Fall Festival

This September, the Chamber, in collaboration with the Town of Cheshire, will bring the community together to support our local businesses, crafters, farms, and local non-profits at the 2026 Fall Festival. The celebration begins on “Food Truck Friday”, September 18th, and continues Saturday, September 19th on the Great Lawn at Bartlem Park, in the heart of our town.

On Friday, visitors can expect a variety of food trucks and entertainment throughout the evening. 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.