Festivals in Old Saybrook, CT.
Craft Shows, Holiday Celebrations
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 Old Saybrook, CT — upcoming
November 2026 (dates not updated)
Saint Paul Christmas Fair
St. Paul Lutheran Church, Old Saybrook, CT
Status: Updated 11/10/2025
This Connecticut Holiday Celebration will have antique/collectibles, commercial/retail, crafts, fine art, fine craft and flea market exhibitors, and 1 food booth. This event will also include: white elephant, basket silent auction, raffle as well as lunch.
February 2027 (dates not updated)
Chili Fest
Main Street, Old Saybrook, CT
Status: Updated 1/15/2026
This Connecticut Food Festival will have no exhibit booths and 28 food booths. Admission tickets are $15.
October 2027 (dates not updated)
Arts & Crafts Festival
Old Saybrook Town Green, Old Saybrook, CT
Status: Updated 9/20/2026
This Connecticut Craft Show will have fine art and fine craft exhibitors, and no food booths.
