Music Festival Gigs 2026–2027Connecticut Cities and TownsBeacon Falls, Bethlehem, Branford, Cheshire, Eastford, Fairfield, Farmington, Goshen, Hartford, Milford, Norwalk, Orange, Oxford, Stratford, Suffield, Unionville, Westport, Woodbridge, WoodstockFind Music Festival Gigs in Connecticut
May 2, 2026Oxford Spring FairOxford Town Hall, Oxford Fire House, Grange, Oxford, CT Status: Updated 2/17/2026
A Family & Kids Festival organized by Oxford Cultural Arts Commission.
This Connecticut Family & Kids Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine craft, flea market 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.
May 9 - 10, 2026Dogwood FestivalGreenfield Hill Church Grounds, Fairfield, CT Status: Updated 8/12/2025
A Craft Show organized by Greenfield Hill Congregational Church.
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.
May 9 - 10, 2026Milford Artisan MarketMilford Green, Milford, CT Status: Updated 1/13/2026
A Craft Show organized by Artisan Events by Ally.
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: martial arts demonstrations, artisan demonstrations.
May 17, 2026Boothe Memorial Park Antique & Classic CarBoothe Memorial Park and Museum, Stratford, CT Status: Updated 2/10/2026
A Family & Kids Festival organized by Port Five.
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.
May 23 - 24, 2026Westport Fine Arts FestivalDowntown, Westport, CT Status: Updated 11/5/2025
An Art Show organized by The Westport Downtown Association.
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 .
May 31, 2026Saint Michael Church Spring FairSt. Michael Church Park, Beacon Falls, CT Status: Updated 9/9/2025
A Festival organized by Saint Michael Church.
This Connecticut Festival will have crafts and fine craft exhibitors, and 3 food booths. There will be 1 stage with Local talent and the hours will be Sun 10am-4pm. This event will also include: vendors & local crafters, ladies' guild baskets, kids' zone, food.
June 11, 2026Strawberry Concert / FestivalCampus of New Horizons Village, Unionville, CT Status: Updated 2/12/2026
A Festival Concert organized by New Horizons Village.
This Connecticut Festival Concert will have no exhibit booths and 2 food booths. There will be 1 stage with Local talent and the hours will be Thu 6:30pm-8:30pm. This event will also include: pony rides, rock painting, balloon animals.
June 13, 2026Orange Congregational Church Strawberry FestivalOrange Fairgrounds at High Plains Community Center, Orange, CT Status: Updated 11/11/2025
A Food Festival organized by Orange Congregational Church UCC.
This Connecticut Food Festival will have antique/collectibles, 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 9am-5pm. This event will also include: strawberries, food, kids' area, facepainting, games, hayrides, red auto show, kids' rides.
June 13, 2026Cheshire Strawberry Festival and Craft FairCheshire Green, Cheshire, CT Status: Updated 2/27/2026
A Festival organized by First Congregational Church of Cheshire Connecticut.
This Connecticut Festival will have corp./information, crafts, film, fine art and fine craft exhibitors, and no food booths. There will be 1 stage with Local talent and the hours will be Sat 10am-4pm.
July 17 - 19, 2026Greater Hartford Festival of JazzBushnell Park, Hartford, CT Status: Updated 9/23/2025
A Jazz Music Festival organized by Greater Hartford Festival of Jazz.
This Connecticut Jazz Music Festival will have commercial/retail, crafts, fine art and fine craft exhibitors, and 23 food booths. There will be 1 stage with National, Regional and Local talent and the hours will be Fri 5pm-11:30pm; Sat 12pm-12 midnight; Sun 12pm-10pm.
July 24 - 26, 2026Falcon Ridge Folk FestivalGoshen Fair Grounds, Goshen, CT Status: Updated 1/14/2026
A Folk Music Festival organized by Falcon Ridge Ltd.
This Connecticut Folk Music Festival will have commercial/retail, corp./information, crafts, fine art, fine craft and homegrown products exhibitors, and 6 food booths. There will be 5 stages with International, National, Regional and Local talent and the hours will be Fri-Sat 9am-11:30pm; Sun 9am-6pm. Admission tickets are $50 - $250. This event will also include: pre fest farm market nd staff open mic, , emerging artist showcase.
August 6 - 8, 2026Podunk Bluegrass Music FestivalGoshen Fairgrounds, Goshen, CT Status: Updated 11/12/2025
A Bluegrass Festival organized by The Podunk Bluegrass Music Festival, Inc..
This Connecticut Bluegrass Festival will have commercial/retail, crafts and fine craft exhibitors, and 4 food booths. There will be 3 stages with National, Regional and Local talent and the hours will be Thu 12pm-10pm; Fri-Sat 10am-11pm. Admission tickets are $25 - $500. This event will also include: workshops, kids academy, band & song writing competitions, camping.
August 14 - 15, 2026Milford Oyster FestivalFowler Field, Milford, CT Status: Updated 12/15/2025
A Festival organized by Annual Milford Oyster Festival, Inc..
This Connecticut Festival will have no exhibit booths and 14 food booths. There will be 1 stage with International, National, Regional and Local talent and the hours will be Fri-Sat 5pm-10pm. Admission tickets are $8. This event will also include: rides, oysters, great food, beer and wine.
August 15 - 16, 2026Farm Festival and Art & Craft FairThe Farm Truck at Hein Farm, Farmington, CT Status: Updated 12/10/2025
A Festival organized by The Farm Truck at Hein Farm.
This Connecticut Festival will have antique/collectibles, crafts, fine art, fine craft and homegrown products exhibitors, and 2 food booths. There will be 1 stage with Regional talent and the hours will be .
June 25 - August 20, 2026Branford Jazz on the Green SeriesBranford Town Green, Branford, CT Status: Updated 2/10/2026
A Festival Concert organized by Branford Parks and Recreation Department.
This Connecticut Festival Concert will have no exhibit booths and no food booths. There will be 1 stage with National, Regional and Local talent and the hours will be .
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