Festivals in Westport, CT.
Art Shows, Festivals, Craft Shows
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 Westport, CT — upcoming
November 7 - 8, 2026
CraftWestport
Staples High School, Westport, CT
Status: Updated 9/2/2026
This Connecticut Art Show will have crafts, fine art and fine craft exhibitors, and 25 food booths. Admission tickets are $6 - $13.
May 2027 (dates not updated)
Westport Fine Arts Festival
Downtown, Westport, CT
Status: Updated 11/5/2025
This Connecticut Art Show will have fine art exhibitors and no food booths. There will be 1 stage with National, Regional and Local talent and the hours will be .
September 2027 (dates not updated)
Gold's Dragoons Charity Polo Match
Fairfield Hunt Club, Westport, CT
Status: Updated 8/17/2026
This Connecticut Sports Event will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft and homegrown products exhibitors, and no food booths. This event will also include: best ladies hat competition, best tailgate, best dressed gentleman.
