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Festivals in Cheshire, CT.
Festivals, Family & Kids Festivals

Featured Events

May 23 - 24, 2026

thevoiceofart.org/call-for-fine-art-festival

(203) 379-0015
Sharon Town Green - Sharon, CT

The Voice of Art is pleased to invite you to its sixth annual outdoor juried fine art show, “Fine Art Festival" in Sharon on the Green. This show will be a highlight for collectors and residents from the Tri-State region, New England and beyond. The Litchfield Hills have a history and reputation of featuring top fine artists from across the country, and also many well-known and beloved New England and CT artists who are widely admired by art enthusiasts.

September 11 - 13, 2026

seaport.org

(203) 838-9444
Veterans Memorial Park - Norwalk, CT

Three days of fun, food, and dazzling free entertainment on multiple stages, plus a myriad of special events for families and friends, from nine to ninety marks just some of the activities planned for the 2026 Norwalk Oyster Festival hosted by the Norwalk Seaport Association at the 35-acre Veteran's Memorial Park in Norwalk. Year 2025 attendance reflects a 2 day event.

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 Cheshire, CT — upcoming

June 13, 2026

Cheshire Strawberry Festival and Craft Fair

Cheshire Green, Cheshire, CT

Status: Updated 2/27/2026

A Festival organized by First Congregational Church of Cheshire Connecticut.
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.
Cheshire Fall Festival
September 2026 (dates not updated)

Cheshire Fall Festival

Bartlem Park, Cheshire, CT

Status: Updated 8/11/2025

A Festival organized by Cheshire Chamber of Commerce.
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.