Saturday September 10th 2022
Saturday September 10th 2022
Eight to the Bar
Friday September 9th 2022
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Fly High with a Hot Air Balloon Experience

Join us Saturday September 10th from 9:00 A.M. – 11:00 AM at Bartlem Park. Cost $20.00 per ride. Sponsored by ReMax Rise Cheshire. Proceeds to offset costs of festival expenses. (Please help us to keep this a free admission festival!) Contact the Cheshire Chamber of Commerce at (203) 272-2345 for more information.

Hot Air Balloon will be tethered. Weather permitting. Kids under 12 must be accompanied by an adult.

Re/Max Rise


Enjoy the entertainment and fireworks at the Cheshire Fall Festival from your reserved spot. Purchase a 10 x 10 VIP spot for your friends and family to enjoy during the Fall Festival on September 9th and 10th. Contact the Cheshire Chamber of Commerce at (203) 272-2345 for more information.

Popcorn and water to be picked up at Cheshire Chamber tent at dusk for fireworks. 10 people maximum in each spot. First come, first serve basis. Payment must be paid in full at time of reservation. No tents allowed!

Package Includes

$ 100
  • 10 x 10 Space
  • Popcorn
  • Water Bottles
  • Friday & Saturday

Welcome to the 34th Cheshire Fall Festival and Market Place Website!

Friday September 9th, 2022 – Food Trucks and Music
Saturday September 10th, 2022 – 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, orchards, and local non-profits at the 2022 Fall Festival. The celebration begins on “Food Truck Friday”, September 9th,and continues to Saturday, September 10th 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 10th, promises to be a beautiful day filled with booths on display, food trucks, performances and demonstrations spanning two stages. Come walk our field and see what our local businesses, crafters, and vendors have been up to. Additionally, we are beyond excited to announce an updated car show for all car enthusiasts! In the evening, you will find musical performances on the main stage and an inspiring display of fireworks for everyone to enjoy. 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!

The 2022 Fall Festival would not be possible without the dedicated volunteers and staff that have committed their time, talent and passion to this special event. Bring your friends and family to Cheshire on September 9th and 10th for the 34th Annual Fall Festival; entertainment, food, music, and more awaits you.


Yetta Augur

President Cheshire Chamber of Commerce.

Contact Us!

2022 Vendor Applications

Downloads for this year’s applications are available now. Click on the links below. The vendor map layout is available now on the application. The field layout will be available in the Spring. Contact the Cheshire Chamber at (203) 272-2345 for more information.

2022 Sponsors

Photo Gallery of Previous Years!