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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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329 Connecticut Events | New Search

Fairs & Festivals in Connecticut 2026–2027

Connecticut Sheep, Wool and Fiber Festival
April 2026 (dates not updated)

Connecticut Sheep, Wool and Fiber Festival

North Haven Fairgrounds, North Haven, CT

Status: Updated 1/30/2025

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This Connecticut Fiber Arts Festival will have 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 9am-4pm. Admission tickets are $10. This event will also include many exhibits and demonstrations.
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Colchester Food Truck & Music Festival
April 2026 (dates not updated)

Colchester Food Truck & Music Festival

Priam Vineyards, Colchester, CT

Status: Updated 3/8/2025

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This Connecticut Festival will have crafts, film and fine craft exhibitors, and 20 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 11am-7pm; Sun 11am-6pm.
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ArborEarth Festival
April 2026 (dates not updated)

ArborEarth Festival

Bartlett Arboretum grounds, Stamford, CT

Status: Updated 3/7/2025

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This Connecticut Family & Kids Festival will have commercial/retail, corp./information and crafts exhibitors, and local food booths. There will be 1 stage with Regional talent and the hours will be Sun 11am-3pm. This event will also include children's activities.
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May Market
May 2026 (dates not updated)

May Market

Hill-Stead Museum Grounds, Farmington, CT

Status: Updated 2/6/2025

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This Connecticut Home and Garden Show will have antique/collectibles, crafts, fine craft and homegrown products exhibitors, and no food booths. There will be Roving Performers with Regional and Local talent and the hours will be Sat 12pm-4pm. Admission tickets are $10. This event will also include: garden demonstrations, workshops, speakers, kids' activities.
2.43/5
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Oxford Spring Fair
May 2026 (dates not updated)

Oxford Spring Fair

Oxford Town Hall, Oxford Fire House, Grange, Oxford, CT

Status: Updated 3/11/2025

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This Connecticut Family & Kids Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine craft and homegrown products exhibitors, and 5 food booths. There will be Roving Performers with Local talent and the hours will be Sat 10am-2pm. This event will also include: touch a truck, petting zoo. kids games.
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Hartford Power Squadron Marine Swap Meet and Craft Show
May 2026 (dates not updated)

Hartford Power Squadron Marine Swap Meet and Craft Show

West Marine, Old Saybrook, CT

Status: Updated 2/6/2025

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This Connecticut Boat Auto Camping Show will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft, flea market and homegrown products exhibitors, and 1 food booth. This event will also include cash raffle.
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Windsor Lions Club Spring Arts & Crafts Festival
May 9, 2026

Windsor Lions Club Spring Arts & Crafts Festival

Windsor Town Green, Windsor, CT

Status: Updated 10/14/2025

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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 part of month long shad derby festival.
2.29/5
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Westville ArtWalk
May 2026 (dates not updated)

Westville ArtWalk

Westville Village, New Haven, CT

Status: Updated 3/18/2025

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This Connecticut Gallery-Exhibition Event will have crafts, fine art and fine craft exhibitors, and no food booths. There will be Roving Performers with talent and the hours will be Mon-Sat 11am-5pm.
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Dogwood Festival
May 9 - 10, 2026

Dogwood Festival

Greenfield Hill Church Grounds, Fairfield, CT

Status: Updated 8/12/2025

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This Connecticut Craft Show will have antique/collectibles, commercial/retail, crafts, fine craft and homegrown products exhibitors, and 6 food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-5pm; Sun 11pm-5pm. This event will also include: local musicians, a capella groups, children's activities, cafe.
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Mile-Long Craft & Tag Sale on the Boardwalk
May 2026 (dates not updated)

Mile-Long Craft & Tag Sale on the Boardwalk

Ocean Beach Park, New London, CT

Status: Updated 3/20/2025

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This Connecticut Flea Market will have antique/collectibles, commercial/retail, crafts, flea market and homegrown products exhibitors, and no food booths. This event will also include raffle.
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Willimantic's Third Thursday Street Fest- May
May 2026 (dates not updated)

Willimantic's Third Thursday Street Fest- May

Historic Downtown on Main Street, Willimantic, CT

Status: Updated 3/14/2025

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This Connecticut Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 20 food booths. There will be 6 stages with Regional and Local talent and the hours will be Thu 6pm-9pm. This event will also include: vendors, children's area.
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South Windsor Armed Forces Day
May 2026 (dates not updated)

South Windsor Armed Forces Day

Nevers Park, South Windsor, CT

Status: Updated 3/8/2025

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This Connecticut Festival will have crafts, film, fine craft and homegrown products exhibitors, and 15 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 5pm-9pm.
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SJB Women's Group Craft Fair
May 2026 (dates not updated)

SJB Women's Group Craft Fair

St. Therese Church, Branford, CT

Status: Updated 3/11/2025

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This Connecticut Festival will have crafts and homegrown products exhibitors, and no food booths.
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Bead Mall Trunk Show
May 2026 (dates not updated)

Bead Mall Trunk Show

The Elks Club Middletown, Middletown, CT

Status: Updated 4/28/2025

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This Connecticut Craft Show will have crafts and fine craft exhibitors, and no food booths. Admission tickets are $2.
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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

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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.
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Southbury Spring Craft Festival
May 17, 2026

Southbury Spring Craft Festival

Wyndham Hotel, Southbury, CT

Status: Updated 12/11/2025

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This Connecticut Craft Show will have corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and no food booths.
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CT Food Truck Battles Festival
May 2026 (dates not updated)

CT Food Truck Battles Festival

Woodtick Recreation, Wolcott, CT

Status: Updated 11/13/2024

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This Connecticut Food Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 40 food booths. There will be 1 stage with National, Regional and Local talent and the hours will be Fri 4pm-8pm; Sat 11am-8pm; Sun 11am-5pm. Admission tickets are $tba.
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Bruce Museum Outdoor Crafts Festival
May 2026 (dates not updated)

Bruce Museum Outdoor Crafts Festival

Bruce Museum Grounds, Greenwich, CT

Status: Updated 1/14/2025

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This Connecticut Art Show will have crafts, fine craft and homegrown products exhibitors, and 4 food booths. There will be Roving Performers with Regional talent and the hours will be . Admission tickets are $10. This event will also include children's craft activites and museum exhibits.
4.14/5
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Boothe Memorial Park Antique & Classic Car
May 2026 (dates not updated)

Boothe Memorial Park Antique & Classic Car

Boothe Memorial Park and Museum, Stratford, CT

Status: Updated 1/15/2025

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This Connecticut Family & Kids Festival will have antique/collectibles exhibitors and 1 food booth. There will be 1 stage with Local talent and the hours will be Sun 9am-4pm. This event will also include the park has many free events from 1:00 pm to 4:00 pm.
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Westport Fine Arts Festival
May 23 - 24, 2026

Westport Fine Arts Festival

Downtown, Westport, CT

Status: Updated 11/5/2025

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This Connecticut Art Show will have fine art exhibitors and no food booths. There will be 1 stage with National, Regional and Local talent and the hours will be .
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Fine Art Festival in Sharon on the Green
May 23 - 24, 2026

Fine Art Festival in Sharon on the Green

Sharon Town Green, Sharon, CT

Status: Updated 12/9/2025

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This Connecticut Craft Show will have crafts, fine art and fine craft exhibitors, and 3 food booths.
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Bethel Blooms Craft Fair
May 2026 (dates not updated)

Bethel Blooms Craft Fair

Municipal Center (front lawn), Bethel, CT

Status: Updated 1/14/2025

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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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Food Trucks on the River - May
May 2026 (dates not updated)

Food Trucks on the River - May

Veteran's Memorial Park, Shelton, CT

Status: Updated 4/3/2025

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This Connecticut Festival will have commercial/retail, crafts, fine art and fine craft exhibitors, and 25 food booths. There will be 1 stage with Regional and Local talent and the hours will be Fri 5pm-10pm; Sat 11am-8pm. This event will also include food trucks.
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Bark in the Park
May 2026 (dates not updated)

Bark in the Park

Latham Park, Stamford, CT

Status: Updated 4/10/2025

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This Connecticut Pet-themed Event will have commercial/retail and corp./information exhibitors, and no food booths. There will be Roving Performers with Local talent and the hours will be Sat 11am-3pm.
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