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.
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.
Saturday
Cheshire Fall Festival
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Balloon Rides 9 AM - 11 AM
Sponsored by ReMax. In front of Cheshire Pool. $20.00 Donation. Children under 12 must be accompanied by an adult.
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Vendors & Crafters 10 AM - 4 PM
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Food Trucks 10 AM - 4 PM
Participating food trucks from Friday evening will start at 10 AM.
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Carnival TBD
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Farmer's Market TBD
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Fireworks Dusk
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Festival End Evening
The Cheshire Fall Festival will commence shortly after the fireworks.
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