GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
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Upcoming Events
Apr
19
Monday Night Cruzin’ Fish Family Farm
Apr 19, 2027 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Apr
20
Dock34 Cruise Night
Apr 20, 2027 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
May
18
Cruise Night with Paradice
May 18, 2027 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
May
18
Joanna’s Restaurant Cruise Night
May 18, 2027 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
May
18
Dock34 Cruise Night
May 18, 2027 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
May
20
Tribury Cruise Night
May 20, 2027 · Woodbury, CT
Regular cars and coffee / cruise-in gathering in Woodbury, CT, drawing classic cars, hot rods, and collector vehicles.
May
21
Joey D’s Cars & Cones
May 21, 2027 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
May
22
The Farmer’s Cow Cafe Weekly Car Show
May 22, 2027 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
May
22
Joey D’s Cars & Cones
May 22, 2027 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
May
24
Monday Night Cruzin’ Fish Family Farm
May 24, 2027 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
May
25
Dock34 Cruise Night
May 25, 2027 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
May
25
Cruise Night with Paradice
May 25, 2027 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
May
27
2027 Greenwich Concours d’Elegance
May 27 – Jun 1, 2027 · Greenwich, CT
Car show in Greenwich, CT, featuring classic, custom, and collector vehicles on display.
Jun
6
Cars and Coffee at the Birdhouse
Jun 6, 2027 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Jun
6
Caffeine & Carburetors (lite)
Jun 6, 2027 · New Canaan, CT
Car show in New Canaan, CT, featuring classic, custom, and collector vehicles on display.
Jun
6
Caffeine & Octane
Jun 6, 2027 · Glastonbury, CT
Regular cars and coffee / cruise-in gathering in Glastonbury, CT, drawing classic cars, hot rods, and collector vehicles.
Jun
8
Joanna’s Restaurant Cruise Night
Jun 8, 2027 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Jun
8
Southington Drive-In Tuesday Night Car Cruise
Jun 8, 2027 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Jun
8
Hank’s Dairy Bar Car Cruise on the Lawn
Jun 8, 2027 · Plainfield, CT
Car show in Plainfield, CT, featuring classic, custom, and collector vehicles on display.
Jun
8
Cruise Night with Paradice
Jun 8, 2027 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.