Festivals in Cheshire, CT.
Festivals, Family & Kids Festivals
Holiday Craft Fair
November 14, 2026
(860) 508-0735
Cromwell High School - Cromwell, CT
The CCCWC Annual Holiday Craft Fair is a successful event that has been supported for over 50 years. The Annual Holiday Craft Fair provides a great opportunity for crafters and artists to showcase their original handcrafted work. We take a special interest in ensuring a profitable and worthwhile day for our crafters. Come and join in the fun!
Frosty's Christmas Festival
November 22, 2026
(203) 233-3167
Aqua Turf Club - Southington, CT
Frosty's Christmas Craft Festival is currently sold out but still accepting applications from crafters and vendors who make and sell their own products for our waiting list. Each Booth will be 8 x 7 and vendors may purchase more than one space. Festivals at this venue normally attract over 3000 shoppers. This event will be heavily advertised in area newspapers, radio and tv ads, street signs and on social media.
Events in Cheshire, CT — upcoming
June 2027 (dates not updated)
Cheshire Strawberry Festival and Craft Fair
Cheshire Green, Cheshire, CT
Status: Updated 2/27/2026
This Connecticut Festival will have corp./information, crafts, film, fine art and fine craft exhibitors, and no food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-4pm.
September 2027 (dates not updated)
Cheshire Fall Festival
Bartlem Park, Cheshire, CT
Status: Updated 8/25/2026
This Connecticut Festival will have antique/collectibles, commercial/retail, crafts, fine art, fine craft and homegrown products exhibitors, and 10 food booths. There will be 2 stages with Regional and Local talent and the hours will be Fri 5pm-9pm; Sat 10am-9pm.
