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Festivals in Windsor, CT.
Festivals, Craft Shows, Holiday Celebrations

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.

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 Windsor, CT — upcoming

May 9, 2026

Windsor Lions Club Spring Arts & Crafts Festival

Windsor Town Green, Windsor, CT

Status: Updated 10/14/2025

A Craft Show organized by Windsor Lions Club.
This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths. This event will also include part of month long shad derby festival.
Windsor Shad Derby Parade and Festival on the Green
May 2026 (dates not updated)

Windsor Shad Derby Parade and Festival on the Green

Windsor Town Green, Windsor, CT

Status: Updated 2/27/2025

A Festival organized by Windsor Jaycees.
This Connecticut Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft, flea market and homegrown products exhibitors, and 20 food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-4pm. This event will also include: parade, beer garden, assorted events.
The Windsor Eco Monarch Fest
September 2026 (dates not updated)

The Windsor Eco Monarch Fest

The Green on Broad Street, Windsor, CT

Status: Updated 8/20/2025

A Festival organized by Suzanne Urban.
This Connecticut Festival will have crafts and fine craft exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-3pm. This event will also include: upcycled planter display, over 30 planters made by area talent.
Windsor Lions Club Fall Arts & Crafts Festival
October 2026 (dates not updated)

Windsor Lions Club Fall Arts & Crafts Festival

Windsor Town Green, Windsor, CT

Status: Updated 5/13/2025

A Craft Show organized by Windsor Lions Club.
This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths. This event will also include chili fest.