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  1. Events
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Connecticut Festivals, Craft Shows, Holiday Celebrations, Vendor Events 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 316 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: Durham Agricultural Fair, Greater Hartford Festival of Jazz and Juried Artisan & Craft Show at Hebron Harvest Fair. Scroll below to view the variety of culture, art, music and entertainment found at Connecticut Festivals, Art Shows, Music Festivals and Craft Shows.

Featured Events
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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308 Connecticut Events | New Search

Fairs & Festivals in Connecticut 2026–2027

Fall Back Spring Ahead Art & Craft Fair
October 2026 (dates not updated)

Fall Back Spring Ahead Art & Craft Fair

Located at The Chester Fairgrounds, Chester, CT

Status: Updated 3/31/2025

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This Connecticut Craft Show will have antique/collectibles, crafts, fine art, fine craft and homegrown products exhibitors, and 1 food booth. This event will also include prize drawing.
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Festival on the Green Craft Show
October 2027 (dates not updated)

Festival on the Green Craft Show

Colchester Town Green, Colchester, CT

Status: Updated 9/24/2026

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This Connecticut Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and tba food booths.
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Waveny Park Arts Festival
October 2027 (dates not updated)

Waveny Park Arts Festival

Waveny Park, New Canaan, CT

Status: Updated 9/23/2026

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This Connecticut Festival will have fine art and fine craft exhibitors, and 5 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sun 10am-4pm.
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Columbus Weekend Arts & Fine Crafts Show
October 2027 (dates not updated)

Columbus Weekend Arts & Fine Crafts Show

Merwinsville Hotel Restoration, Inc., New Milford, CT

Status: Updated 10/6/2025

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths. Admission tickets are $3 - $35.
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Buells' Orchard Harvest Festival
October 2027 (dates not updated)

Buells' Orchard Harvest Festival

Buell's Orchard, Eastford, CT

Status: Updated 2/10/2026

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This Connecticut Festival will have no exhibit booths and no food booths. There will be 1 stage with Regional and Local talent and the hours will be Mon, Sat 10am-4pm; Sun 1pm-4pm. This event will also include hayrides.
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Autumn Arts Festival
October 2026 (dates not updated)

Autumn Arts Festival

Madison Town Green, Madison, CT

Status: Updated 9/15/2025

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This Connecticut Art Show will have crafts, fine art and fine craft exhibitors, and 3 food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-5pm; Sun 12pm-5pm.
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Fairfield Harvest Market
October 2027 (dates not updated)

Fairfield Harvest Market

Old Town Hall Green, Fairfield, CT

Status: Updated 7/16/2026

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This Connecticut Holiday Celebration will have antique/collectibles, commercial/retail, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 8 food booths. There will be Roving Performers with Local talent and the hours will be Sat 10am-4pm. This event will also include halloween dog costume parade.
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The Blessing Pantry Fall Fair
October 2027 (dates not updated)

The Blessing Pantry Fall Fair

Seymour, Seymour, CT

Status: Updated 3/23/2026

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This Connecticut Craft Show will have antique/collectibles, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and no food booths. There will be 2 stages with Local talent and the hours will be Sat 10am-2pm. This event will also include free children bounce house and face painting.
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Newtown United Methodist Church Fall Arts & Craft Fair
October 2027 (dates not updated)

Newtown United Methodist Church Fall Arts & Craft Fair

Reed Intermediate School, Newtown, CT

Status: Updated 10/9/2026

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This Connecticut Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and no food booths.
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Zion Scarecrow Festival
October 2027 (dates not updated)

Zion Scarecrow Festival

Zion Lutheran Church, Wallingford, CT

Status: Updated 8/20/2026

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This Connecticut Craft Show will have antique/collectibles, crafts, flea market and homegrown products exhibitors, and 3 food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-3pm. This event will also include: craft fair, hayride, kids games, scarecrow building, scarecrow voting, baked goods.
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Glastonbury Apple Harvest & Music Festival
October 2027 (dates not updated)

Glastonbury Apple Harvest & Music Festival

Riverfront Park, Glastonbury, CT

Status: Updated 6/19/2026

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This Connecticut Festival will have antique/collectibles, commercial/retail, crafts, fine art, fine craft and homegrown products exhibitors, and 25 food booths. There will be 4 stages with International, National, Regional and Local talent and the hours will be Fri 5pm-10pm; Sat 10am-10pm; Sun 11am-4pm. Admission tickets are $5 - $12. This event will also include: harvest pub, amusement rides, kids zone, 55 bands on 5 stages.
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Roseland Cottage Fine Arts & Crafts Festival
October 2027 (dates not updated)

Roseland Cottage Fine Arts & Crafts Festival

Roseland Cottage, Woodstock, CT

Status: Updated 1/13/2026

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and Tbd food booths. There will be 1 stage with Regional and Local talent and the hours will be . Admission tickets are $5.
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Connecticut Food Truck & Wine Festival
October 2027 (dates not updated)

Connecticut Food Truck & Wine Festival

Priam Vineyards, Colchester, CT

Status: Updated 10/16/2026

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This Connecticut Food Festival will have crafts, fine craft and homegrown products exhibitors, and 20 food booths. There will be 1 stage with Local talent and the hours will be Sat 11am-6pm; Sun 11am-5pm.
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Milford Artisan Market - October
October 2027 (dates not updated)

Milford Artisan Market - October

Milford Green, Milford, CT

Status: Updated 1/13/2026

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and 4 food booths. There will be 2 stages with Regional and Local talent and the hours will be Sat-Sun 10am-4pm. This event will also include: kid's area, vendor demonstrations.
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Milford Artisan Market
October 2027 (dates not updated)

Milford Artisan Market

Milford Green, Milford, CT

Status: Updated 8/11/2026

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and 5 food booths. There will be 2 stages with Local talent and the hours will be Sat-Sun 10am-4pm. This event will also include artisan demonstrations.
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Pumpkin Fest
October 2027 (dates not updated)

Pumpkin Fest

Bunny McGuire Park, Canaan, CT

Status: Updated 4/29/2026

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This Connecticut Vendor Event will have antique/collectibles, commercial/retail, crafts, film, fine art, fine craft and homegrown products exhibitors, and 5 food booths. There will be 1 stage with Local talent and the hours will be Sun 10am-3pm. This event will also include kids' activities.
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Hall-O-Weekend
October 2027 (dates not updated)

Hall-O-Weekend

Milford Green/Downtown Milford, Milford, CT

Status: Updated 9/27/2026

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This Connecticut Family & Kids Festival will have commercial/retail, corp./information, crafts and homegrown products exhibitors, and local food booths.
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Holiday Craft Fair
October 2027 (dates not updated)

Holiday Craft Fair

Saint Thomas Parish Gym, Fairfield, CT

Status: Updated 10/21/2026

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This Connecticut Holiday Celebration will have antique/collectibles, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and no food booths. This event will also include raffles.
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Nineteen Annual Pre-Holiday Craft / Wares Fair
October 2027 (dates not updated)

Nineteen Annual Pre-Holiday Craft / Wares Fair

St. Thomas Aquinas Parish Center (GYM), Fairfield, CT

Status: Updated 9/13/2026

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This Connecticut Festival will have antique/collectibles, corp./information, crafts, film, fine craft and homegrown products exhibitors, and no food booths.
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New Fairfield Craft and Bake Sale
October 2027 (dates not updated)

New Fairfield Craft and Bake Sale

New Fairfield Senior Center, New Fairfield, CT

Status: Updated 10/19/2026

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This Connecticut Craft Show will have crafts exhibitors and no food booths. This event will also include cupcake decorating for the kids.
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