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
September 5, 2026
Bethel Holiday Weekend Craft Festival
Municipal Center (front lawn), Bethel, CT
Status: Updated 6/29/2026
August 2 - September 6, 2026
Walnut Beach Summer Concert Series
Walnut Beach Pavillion, Milford, CT
Status: Updated 6/21/2026
September 12, 2026
Saint James Fall Fair
St. James Episcopal Church, Farmington, CT
Status: Updated 6/11/2026
September 11 - 13, 2026
East Haven Fall Festival
Town Green, East Haven, CT
Status: Updated 8/17/2026
September 19, 2026
Outdoor Harvest Craft Festival & Car Show
St Martha's Church grounds, Enfield, CT
Status: Updated 2/27/2026
September 25 - 26, 2026
Devon Rotary Oktoberfest
Rotary Pavillion, Fowler Field, Milford, CT
Status: Updated 5/12/2026
October 3, 2026
Bethel Autumn Craft Festival
Municipal Center (front lawn), Bethel, CT
Status: Updated 6/29/2026
October 10, 2026
Windsor Lions Club Spring Arts & Crafts Festival
Windsor Town Green, Windsor, CT
Status: Updated 8/12/2026
October 10, 2026
Windsor Lions Club Fall Arts & Crafts Festival
Windsor Town Green, Windsor, CT
Status: Updated 2/11/2026
October 2 - 11, 2026
Southington Apple Harvest Festival Arts and Crafts Show
Southington Town Green, Southington, CT
Status: Updated 4/28/2026
October 10 - 11, 2026
Connecticut Garlic & Harvest Festival
Bethlehem Fairgrounds, Bethlehem, CT
Status: Updated 8/12/2026
October 17, 2026
Fairfield Harvest Market
Old Town Hall Green, Fairfield, CT
Web: commerce.fairfieldctchamber.com/events/deta..
Status: Updated 7/16/2026
November 7, 2026
Shelton Autumn Craft Festival
Hyatt House Hotel, Shelton, CT
Status: Updated 12/7/2025
November 14, 2026
Christmas Bazaar and Craft Fair
Our Lady of Assumption Church Hall, Woodbridge, CT
Status: Updated 6/22/2026
November 14, 2026
Fall Into Winter Craft Fair
Holy Family Church Hall & Classrooms / St Jeanne Jugan Parish, Enfield, CT
Status: Updated 6/11/2026
November 14, 2026
West Bristol School Holiday Craft & Vendor Fair
West Bristol School, Bristol, CT
Status: Updated 2/10/2026
November 22, 2026
Southbury Autumn Craft Festival
Wyndham Hotel, Southbury, CT
Status: Updated 12/7/2025
November 22, 2026
Frosty's Christmas Festival
Aqua Turf Club, Southington, CT
Status: Updated 1/1/2026
