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
19
Cruise Night – Open Cruise
Oct 19, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
19
Lenny Incandella Memorial Cruise Night
Oct 19, 2026 · Willimantic, CT
Regular cars and coffee / cruise-in gathering in Willimantic, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
19
Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show
Oct 19, 2026 · Willington, CT
Car show in Willington, CT, featuring classic, custom, and collector vehicles on display.
Oct
19
Monday Night Cruisn’
Oct 19, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Oct
20
Joanna’s Restaurant Cruise Night
Oct 20, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
20
Dock34 Cruise Night
Oct 20, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
20
Cruise Night with Paradice
Oct 20, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
20
Southington Drive-In Tuesday Night Car Cruise
Oct 20, 2026 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
20
Litchfield Crossings Tuesday Cruise
Oct 20, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
20
Two-Wheel Tuesdays
Oct 20, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Oct
22
Prospect Auto Club Cruise Night
Oct 22, 2026 · Prospect, CT
Regular cars and coffee / cruise-in gathering in Prospect, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
22
Tribury Cruise Night
Oct 22, 2026 · Woodbury, CT
Regular cars and coffee / cruise-in gathering in Woodbury, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
22
Crusin East Thursday Cruise
Oct 22, 2026 · Milford, CT
Regular cars and coffee / cruise-in gathering in Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
23
Trantolo & Trantolo Presents: Cruisin’ @ CT Golf Land
Oct 23, 2026 · Vernon, CT
Regular cars and coffee / cruise-in gathering in Vernon, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
23
2026 MiataCon
Oct 23, 2026 · Lakeville, CT
Car show in Lakeville, CT, featuring classic, custom, and collector vehicles on display.
Oct
23
Joey D’s Cars & Cones
Oct 23, 2026 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
Oct
24
Hot Rod Hootenanny at the Farm at Carter Hill
Oct 24, 2026 · Marlborough, CT
Car show in Marlborough, CT, featuring classic, custom, and collector vehicles on display.
Oct
24
Cam Jammers Cars and Coffee
Oct 24, 2026 · Windsor Locks, CT
Car show in Windsor Locks, CT, featuring classic, custom, and collector vehicles on display.
Oct
24
The Rotary Club of Plainfield 4th Annual Car Show
Oct 24, 2026 · Plainfield, CT
Car show in Plainfield, CT, featuring classic, custom, and collector vehicles on display.
Oct
24
Farmers Cow Car Show
Oct 24, 2026 · Berlin, CT
Car show in Berlin, 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.