GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
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Past Events
Aug
26
State Line Propane & Oil Car Show
Aug 26, 2026 · Granby, CT
Car show in Granby, CT, featuring classic, custom, and collector vehicles on display.
Aug
26
State Line Car Show
Aug 26, 2026 · Granby, CT
Car show in Granby, CT, featuring classic, custom, and collector vehicles on display.
Aug
26
Cruise Nights at The Enfield Knights Council
Aug 26, 2026 · Enfield, CT
Regular cars and coffee / cruise-in gathering in Enfield, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
26
Da Andrea Restaurant Classic Car Cruise
Aug 26, 2026 · Westbrook, CT
Car show in Westbrook, CT, featuring classic, custom, and collector vehicles on display.
Aug
25
Dock34 Cruise Night
Aug 25, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
25
Two-Wheel Tuesdays
Aug 25, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Aug
25
Joanna's Cruise Night
Aug 25, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
25
Joanna’s Restaurant Classic Car Shows
Aug 25, 2026 · Somers, CT
Car show in Somers, CT, featuring classic, custom, and collector vehicles on display.
Aug
25
Southington Drive-In Tuesday Night Car Cruise
Aug 25, 2026 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
25
Litchfield Crossings Tuesday Cruise
Aug 25, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
24
Monday Night Cruzin’ Fish Family Farm
Aug 24, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Aug
24
Connecticut Valley Brewing Company Cruise Night
Aug 24, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
24
Cruise Night – Open Cruise
Aug 24, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
24
Monday Night Cruisn’
Aug 24, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Aug
24
Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show
Aug 24, 2026 · Willington, CT
Car show in Willington, CT, featuring classic, custom, and collector vehicles on display.
Aug
24
Cruise Night: Oldsmobile/Buick/Cadillac/Pontiac
Aug 24, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
23
Blood Sweat and Gear's Car's and Coffee.
Aug 23, 2026 · Milford, CT
Car show in Milford, CT, featuring classic, custom, and collector vehicles on display.
Aug
23
Air-Cooled at the Orchard
Aug 23, 2026 · 9 AM – 3 PM · Middlefield, CT
The Connecticut Volkswagen Association and Connecticut CORSA present Air-Cooled at the Orchard at Lyman Orchards, 32 Reeds Gap Road in Middlefield. The show is open to air-cooled Volkswagens, Porsches and Corvairs. Show-car entry is $10 and spectator admission is free. The event is rain or shine.
Aug
23
Cars and Coffee at the Birdhouse
Aug 23, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
23
Caffeine & Carburetors (lite)
Aug 23, 2026 · New Canaan, CT
Car show in New Canaan, CT, featuring classic, custom, and collector vehicles on display.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.