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
1
Tribury Cruise Night
Oct 1, 2026 · Woodbury, CT
Regular cars and coffee / cruise-in gathering in Woodbury, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
1
Prospect Auto Club Cruise Night
Oct 1, 2026 · Prospect, CT
Regular cars and coffee / cruise-in gathering in Prospect, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
1
Cruise Night at Connecticut Valley Brewing
Oct 1, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
1
Connecticut Seaport Car Club’s 2026 Cruise Nights
Oct 1, 2026 · Fairfield, CT
Regular cars and coffee / cruise-in gathering in Fairfield, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
1
Prospect Auto Club Car Show at Senor Panchos
Oct 1, 2026 · Prospect, CT
Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.
Oct
1
Crusin East Thursday Cruise
Oct 1, 2026 · Milford, CT
Regular cars and coffee / cruise-in gathering in Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
1
Prospect Car Show
Oct 1, 2026 · Prospect, CT
Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.
Oct
2
Trantolo & Trantolo Presents: Cruisin’ @ CT Golf Land
Oct 2, 2026 · Vernon, CT
Regular cars and coffee / cruise-in gathering in Vernon, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
3
Farmers Cow Car Show
Oct 3, 2026 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
Oct
3
The Farmer’s Cow Cafe Weekly Car Show
Oct 3, 2026 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
Oct
3
Bristol Auto Club Cruise Night
Oct 3, 2026 · Bristol, CT
Regular cars and coffee / cruise-in gathering in Bristol, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
3
Bill’s Drive-In Saturday Cruise
Oct 3, 2026 · Monroe, CT
Regular cars and coffee / cruise-in gathering in Monroe, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
4
Breast Cancer Awareness Car Show
Oct 4, 2026 · SOUTHINGTON, CT
Car show in SOUTHINGTON, CT, featuring classic, custom, and collector vehicles on display.
Oct
4
Blood Sweat and Gear's Car's and Coffee.
Oct 4, 2026 · Milford, CT
Car show in Milford, CT, featuring classic, custom, and collector vehicles on display.
Oct
4
4th Annual Kickin’ Country Car, Truck and Tractor Show
Oct 4, 2026 · Woodbury, CT
Car show in Woodbury, CT, featuring classic, custom, and collector vehicles on display.
Oct
5
Cruise Night: 60’s Night
Oct 5, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
5
Cruise Night – Open Cruise
Oct 5, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
5
Monday Night Cruisn’
Oct 5, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Oct
5
Cruise Night at Connecticut Valley Brewing
Oct 5, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
5
Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show
Oct 5, 2026 · Willington, CT
Car show in Willington, 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.