GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
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Upcoming Events
Oct
12
Monday Night Cruisn’
Oct 12, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Oct
12
Cruise Night at Connecticut Valley Brewing
Oct 12, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
12
Cruise Night – Open Cruise
Oct 12, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
12
Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show
Oct 12, 2026 · Willington, CT
Car show in Willington, CT, featuring classic, custom, and collector vehicles on display.
Oct
13
Litchfield Crossings Tuesday Cruise
Oct 13, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
13
Two-Wheel Tuesdays
Oct 13, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Oct
13
Dock34 Cruise Night
Oct 13, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
13
Cruise Night with Paradice
Oct 13, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
14
Car show @ Beer Garden @ Bart’s
Oct 14, 2026 · Windsor, CT
Car show in Windsor, CT, featuring classic, custom, and collector vehicles on display.
Oct
15
Prospect Car Show
Oct 15, 2026 · Prospect, CT
Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.
Oct
15
Prospect Auto Club Cruise Night
Oct 15, 2026 · Prospect, CT
Regular cars and coffee / cruise-in gathering in Prospect, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
15
Tribury Cruise Night
Oct 15, 2026 · Woodbury, CT
Regular cars and coffee / cruise-in gathering in Woodbury, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Trantolo & Trantolo Presents: Cruisin’ @ CT Golf Land
Oct 16, 2026 · Vernon, CT
Regular cars and coffee / cruise-in gathering in Vernon, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
17
Farmers Cow Car Show
Oct 17, 2026 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
Oct
17
Jags and Java
Oct 17, 2026 · Wallingford, CT
Car show in Wallingford, CT, featuring classic, custom, and collector vehicles on display.
Oct
18
Blood Sweat and Gear's Car's and Coffee.
Oct 18, 2026 · Milford, CT
Car show in Milford, CT, featuring classic, custom, and collector vehicles on display.
Oct
18
Cars and Coffee at the Birdhouse
Oct 18, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Caffeine & Octane
Oct 18, 2026 · Glastonbury, CT
Regular cars and coffee / cruise-in gathering in Glastonbury, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Caffeine & Carburetors (lite)
Oct 18, 2026 · New Canaan, CT
Car show in New Canaan, CT, featuring classic, custom, and collector vehicles on display.
Oct
19
Monday Night Cruzin’ Fish Family Farm
Oct 19, 2026 · Bolton, CT
Car show in Bolton, 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.