Festivals in New Canaan, CT.
Festivals, Family & Kids Festivals
Fairfield Harvest Market
October 17, 2026
commerce.fairfieldctchamber.com/events/deta..
(203) 255-1011
Old Town Hall Green - Fairfield, CT
Fairfield Farmers Market Vendors, Fairfield Rotary Beer Garden Guess the Weight of the Giant Pumpkin, Apples, Cider, Food Trucks, Jewelry, Apparel, Food Items, Home Décor, Crafts, Furniture, Pet Products, DJ Scott providing music. Rain Date - October 24, 2026
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.
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Events in New Canaan, CT — upcoming
October 2026 (dates not updated)
Harvest Fest
New Canaan Nature Center, New Canaan, CT
Status: Updated 9/21/2025
This Connecticut Wine-Beer Event will have homegrown products exhibitors and local food booths. There will be 1 stage with Regional talent and the hours will be Sat 7pm-10pm. Admission tickets are $85 - $250.
October 11, 2026
Waveny Park Arts Festival
Waveny Park, New Canaan, CT
Status: Updated 9/23/2026
This Connecticut Festival will have fine art and fine craft exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sun 10am-4pm.
October 2026 (dates not updated)
Fall Fair
New Canaan Nature Center, New Canaan, CT
Status: Updated 10/1/2025
This Connecticut Festival will have no exhibit booths and tba food booths. There will be 1 stage with Regional and Local talent and the hours will be Fri 5pm-9pm; Sat 10am-6pm; Sun 12pm-5pm.
