GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
Browse cars for sale in Connecticut →Filters
Narrow the events below by city, ZIP, or event type.
Upcoming Events
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
6
Dock 34 Cruise Night
Oct 6, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
6
Litchfield Crossings Tuesday Cruise
Oct 6, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
6
Two-Wheel Tuesdays
Oct 6, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Oct
7
Car show @ Beer Garden @ Bart’s
Oct 7, 2026 · Windsor, CT
Car show in Windsor, CT, featuring classic, custom, and collector vehicles on display.
Oct
8
Crusin East Thursday Cruise
Oct 8, 2026 · Milford, CT
Regular cars and coffee / cruise-in gathering in Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
8
Prospect Car Show
Oct 8, 2026 · Prospect, CT
Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.
Oct
8
Prospect Auto Club Cruise Night
Oct 8, 2026 · Prospect, CT
Regular cars and coffee / cruise-in gathering in Prospect, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
8
Cruise Night at Connecticut Valley Brewing
Oct 8, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
10
Nexgen trunk or treat Car Show
Oct 10, 2026 · Bristol, CT
Car show in Bristol, CT, featuring classic, custom, and collector vehicles on display.
Oct
10
Oct. 10: Driver Education @ Lime Rock Park
Oct 10, 2026 · Lakeville, CT
Regular cars and coffee / cruise-in gathering in Lakeville, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
10
Farmers Cow Car Show
Oct 10, 2026 · Berlin, CT
Car show in Berlin, CT, featuring classic, custom, and collector vehicles on display.
Oct
11
Cars for Kids Automobile Show
Oct 11, 2026 · Litchfield, CT
Car show in Litchfield, CT, featuring classic, custom, and collector vehicles on display.
Oct
11
Cars and Coffee at the Birdhouse
Oct 11, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
11
Caffeine & Carburetors (lite)
Oct 11, 2026 · New Canaan, CT
Car show in New Canaan, CT, featuring classic, custom, and collector vehicles on display.
Oct
11
Blood Sweat and Gears Cars and Coffee
Oct 11, 2026 · Milford, CT
Regular cars and coffee / cruise-in gathering in Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
11
Caffeine & Octane
Oct 11, 2026 · Glastonbury, CT
Regular cars and coffee / cruise-in gathering in Glastonbury, CT, drawing classic cars, hot rods, and collector vehicles.
Oct
12
Monday Night Cruzin’ Fish Family Farm
Oct 12, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
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
Monday Night Cruisn’
Oct 12, 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.