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Connecticut Festivals, Holiday Celebrations, Craft Shows, Family & Kids Festivals 2026–2027.

Connecticut spans just 110 miles from east to west and 70 from north to south. But the compact Constitution State has everything you need to unplug - and recharge! With 330 festivals celebrating culture, the arts, beer, blues and barbecue, Shakespeare, strawberries, sailing and everything in between, there's something for everyone! These three events are just the beginning: Sailfest, Durham Agricultural Fair and Greater Hartford Festival of Jazz. Scroll below to view the variety of culture, art, music and entertainment found at Connecticut Festivals, Art Shows, Music Festivals and Craft Shows.

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328 Connecticut Events | New Search

Fairs & Festivals in Connecticut 2026–2027

Holidays on Main
December 2026 (dates not updated)

Holidays on Main

Main Street, Old Wethersfield, Wethersfield, CT

Status: Updated 4/11/2025

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This Connecticut Holiday Celebration will have commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 8 food booths. There will be 1 stage with Local talent and the hours will be Thu 5pm-9pm. This event will also include: caroling, tree lighting, horse & wagon, santa visits.
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Lamplight Stroll
December 2026 (dates not updated)

Lamplight Stroll

Milford Green, Milford, CT

Status: Updated 8/5/2025

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This Connecticut Holiday Celebration will have commercial/retail, crafts, fine art and fine craft exhibitors, and tba food booths. This event will also include: shopping, singalongs, horse & carriage ride, carolers, santa.
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Shelton Holiday Craft Festival
December 5, 2026

Shelton Holiday Craft Festival

Hyatt House Hotel, Shelton, CT

Status: Updated 12/7/2025

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This Connecticut Craft Show will have corp./information, crafts, fine art and fine craft exhibitors, and no food booths.
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First Church of South Windsor Holiday Craft Fair
December 2026 (dates not updated)

First Church of South Windsor Holiday Craft Fair

Church Basement, South Windsor, CT

Status: Updated 3/11/2025

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This Connecticut Craft Show will have crafts and fine craft exhibitors, and no food booths. There will be Roving Performers with Local talent and the hours will be Fri 5pm-8pm; Sat 9am-2pm.
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Christmas Town Festival
December 2026 (dates not updated)

Christmas Town Festival

Junction Route 61 and Route 132, Bethlehem, CT

Status: Updated 8/25/2025

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This Connecticut Holiday Celebration will have crafts exhibitors and 10 food booths. There will be 2 stages with Local talent and the hours will be Fri 5pm-9:30pm; Sat 9:30am-4pm. This event will also include: "santa made me do it" 5k race, scavenger hunt, kids crafts, vehicle decorating.
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Christmas Faire
December 2026 (dates not updated)

Christmas Faire

Deep River Congregational Church, Deep River, CT

Status: Updated 11/20/2025

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This Connecticut Holiday Celebration will have antique/collectibles, crafts and homegrown products exhibitors, and 3 food booths. This event will also include children's workshop.
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Holiday Fair
December 2026 (dates not updated)

Holiday Fair

Holy Trinity Lutheran Church, Terryville, CT

Status: Updated 11/24/2025

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This Connecticut Holiday Celebration will have crafts exhibitors and no food booths. This event will also include: crafts, fresh greens, homemade soups, cookie walk.
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Bacon Academy Sleigh Bells Arts & Crafts Fair
December 2026 (dates not updated)

Bacon Academy Sleigh Bells Arts & Crafts Fair

Bacon Academy High School, Colchester, CT

Status: Updated 4/8/2025

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This Connecticut Craft Show will have antique/collectibles, crafts, fine craft and homegrown products exhibitors, and 2 food booths.
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Cromwell Mayor's Tree Lighting
December 2026 (dates not updated)

Cromwell Mayor's Tree Lighting

Cromwell Town Green, Cromwell, CT

Status: Updated 11/6/2025

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This Connecticut Family & Kids Festival will have no exhibit booths and 4 food booths. This event will also include: caroling, hot chocolate, cookies, petting zoo, photo booth, food trucks.
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Christmas Bazaar
December 2026 (dates not updated)

Christmas Bazaar

Somers Congregational Church, Somers, CT

Status: Updated 12/4/2025

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This Connecticut Holiday Celebration will have commercial/retail, crafts, fine art, fine craft and homegrown products exhibitors, and no food booths. This event will also include lunch is available.
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Christmas Market
December 2026 (dates not updated)

Christmas Market

School Gym, Torrington, CT

Status: Updated 10/7/2025

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This Connecticut Craft Show will have commercial/retail and crafts exhibitors, and no food booths. There will be Roving Performers with National and Local talent and the hours will be Sat 10am-6am. This event will also include school gingerbread and art contests.
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Scandinavian Club Christmas Market
December 2026 (dates not updated)

Scandinavian Club Christmas Market

Scandinavian Club, Fairfield, CT

Status: Updated 7/8/2025

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This Connecticut Holiday Celebration will have commercial/retail, crafts, fine art, fine craft and homegrown products exhibitors, and no food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-3pm. This event will also include: scandinavian holiday lunch, raffle, santa.
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Holiday Craft Fair & Marketplace
December 2026 (dates not updated)

Holiday Craft Fair & Marketplace

West District School, Unionville, CT

Status: Updated 11/8/2025

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths. This event will also include: cupcake making, ornament making, santa photos, face painting.
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Christmas Craft Fair and Boutique
December 2026 (dates not updated)

Christmas Craft Fair and Boutique

Woodbury Middle School, Woodbury, CT

Status: Updated 4/14/2025

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This Connecticut Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and no food booths. This event will also include festival of wreaths - silent auction for beautifully decorated fresh wreaths.
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Holiday Craft Fair
December 2026 (dates not updated)

Holiday Craft Fair

Bristol Historical Society, Bristol, CT

Status: Updated 11/4/2025

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This Connecticut Craft Show will have antique/collectibles and crafts exhibitors, and no food booths.
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Saint Matthew H.S.A. Craft/Vendor Show
December 2026 (dates not updated)

Saint Matthew H.S.A. Craft/Vendor Show

St. Matthew School, Forestville, CT

Status: Updated 12/1/2025

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This Connecticut Craft Show will have antique/collectibles, crafts, fine art, fine craft and homegrown products exhibitors, and no food booths. This event will also include: raffle, lunch served, bake sale.
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Knights of Saint Patrick Fifth Winter Craft Fair
December 2026 (dates not updated)

Knights of Saint Patrick Fifth Winter Craft Fair

Knights of St. Patrick, New Haven, CT

Status: Updated 10/22/2025

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This Connecticut Craft Show will have antique/collectibles, crafts, fine art, fine craft and flea market exhibitors, and no food booths. This event will also include: raffle, specialty cocktails, food for purchase.
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Torrington Holiday Craft and Gift Fair
December 2026 (dates not updated)

Torrington Holiday Craft and Gift Fair

Historic Armory Building, Torrington, CT

Status: Updated 11/6/2025

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This Connecticut Craft Show will have commercial/retail, crafts, fine art and fine craft exhibitors, and no food booths.
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Saint Ann Christmas Fair
December 2026 (dates not updated)

Saint Ann Christmas Fair

Saint Ann Parish Center, Milford, CT

Status: Updated 12/7/2025

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This Connecticut Holiday Celebration will have crafts, fine art and fine craft exhibitors, and no food booths.
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Haddam Killingworth Holiday Craft Fair
December 2026 (dates not updated)

Haddam Killingworth Holiday Craft Fair

Haddam Killingworth Middle School, Killingworth, CT

Status: Updated 12/2/2025

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This Connecticut Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and 4 food booths. This event will also include raffle.
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Chaplin PTO Craft Fair
December 2026 (dates not updated)

Chaplin PTO Craft Fair

Chaplin Elementary School, Chaplin, CT

Status: Updated 11/8/2025

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This Connecticut Craft Show will have antique/collectibles, commercial/retail, crafts, film, fine art, fine craft and homegrown products exhibitors, and no food booths. This event will also include breakfast with santa.
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Short Short Story Film Festival
November - December 2026 (dates not updated)

Short Short Story Film Festival

Online only at

Status: Updated 11/21/2025

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This Connecticut will have no exhibit booths and no food booths. Admission tickets are $10 - $13.
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Heritage Holiday Church Fair
December 2026 (dates not updated)

Heritage Holiday Church Fair

First Congregational Church of South Windsor, South Windsor, CT

Status: Updated 9/9/2025

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This Connecticut Craft Show will have crafts and fine craft exhibitors, and no food booths.
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CraftWestport
December 2026 (dates not updated)

CraftWestport

Staples High School, Westport, CT

Status: Updated 10/21/2025

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This Connecticut Art Show will have crafts, fine art and fine craft exhibitors, and 25 food booths. Admission tickets are $6 - $13.
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