Holiday Events in Connecticut 2026–2027
Attend the Most Exciting Holiday Events This Year
If you’re looking for holiday-themed events in Connecticut, we’ve got you covered. Browse through dozens of updated events to add a touch of festivity, fun, and spontaneity to the holidays! If you don’t have something planned, you’ll manage to turn things around at the last minute and make your holidays extra special. At FestivalNet, we don’t just cover Christmas and New Year’s. You’ll also find countless exciting events, shows, festivals, and fairs for the Fourth of July, Halloween, Thanksgiving, Valentine’s Day, and a wide range of other exciting celebrations! Whether you’re looking for the perfect holiday event to enjoy as a couple, with friends, or with your family, you’ll find a plethora of options here. Ready to get started? Browse through some of the most anticipated events of the year to let the merrymaking begin!
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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Holiday Events — upcoming
December 5, 2026
Bacon Academy Sleigh Bells Arts & Crafts Fair
Bacon Academy High School, Colchester, CT
Status: Updated 5/12/2026
December 5, 2026
60th Annual DRCC Christmas Faire
Deep River Congregational Church, Deep River, CT
Status: Updated 6/25/2026
December 5, 2026
Holidays on Main
Main Street, Old Wethersfield, Wethersfield, CT
Status: Updated 4/14/2026
December 5, 2026
Shelton Holiday Craft Festival
Hyatt House Hotel, Shelton, CT
Status: Updated 12/7/2025
December 5, 2026
Christmas Craft Fair and Boutique
Woodbury Middle School, Woodbury, CT
Status: Updated 3/27/2026
December 4 - 6, 2026
First Church of South Windsor Holiday Craft Fair
Church Basement, South Windsor, CT
Status: Updated 8/11/2026
December 6, 2026
41st Annual Holiday Festival/Newtown CT Holiday Market
Main St. Newtown, Edmond Town Hall, Trinity Church, CHB Library, Newtown, CT
Status: Updated 4/22/2026
December 6, 2026
Haddam Killingworth Holiday Craft Fair
Haddam Killingworth Middle School, Killingworth, CT
Status: Updated 3/10/2026
December 12, 2026
Hebron Holiday Craft Fair
Hebron Elementary School, Hebron, CT
Status: Updated 7/18/2026
