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.
Past Events
Sep
24
Prospect Car Show
Sep 24, 2026 · Prospect, CT
Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.
Sep
24
Norbrook Farm Brewery Cruise Night
Sep 24, 2026 · Colebrook, CT
Regular cars and coffee / cruise-in gathering in Colebrook, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
23
Wednesday Night Cruise at Fritz’s
Sep 23, 2026 · Oxford, CT
Regular cars and coffee / cruise-in gathering in Oxford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
23
Car show @ Beer Garden @ Bart’s
Sep 23, 2026 · Windsor, CT
Car show in Windsor, CT, featuring classic, custom, and collector vehicles on display.
Sep
23
THOMPSON ROD AND GUN CLUB CAR CRUISE
Sep 23, 2026 · Thompson, CT
Car show in Thompson, CT, featuring classic, custom, and collector vehicles on display.
Sep
23
Wednesday Night Cruise at Orem’s Diner
Sep 23, 2026 · Wilton, CT
Regular cars and coffee / cruise-in gathering in Wilton, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
23
Cruise Nights at the Knights Council 50
Sep 23, 2026 · Enfield, CT
Regular cars and coffee / cruise-in gathering in Enfield, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Southington Drive-In Tuesday Night Car Cruise
Sep 22, 2026 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Cruise Night with Paradice
Sep 22, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Classic Car Cruise Night
Sep 22, 2026 · Trumbull, CT
Regular cars and coffee / cruise-in gathering in Trumbull, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Cruise Night
Sep 22, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Two-Wheel Tuesdays
Sep 22, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Sep
22
Dock34 Cruise Night
Sep 22, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Joanna's Cruise Night
Sep 22, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
22
Litchfield Crossings Tuesday Cruise
Sep 22, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
21
Monday Night Cruisn’
Sep 21, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Sep
21
Lenny Incandella Memorial Cruise Night
Sep 21, 2026 · Willimantic, CT
Regular cars and coffee / cruise-in gathering in Willimantic, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
21
Monday Night Cruzin’ Fish Family Farm
Sep 21, 2026 · Bolton, CT
Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.
Sep
21
Cruise Night – Open Cruise
Sep 21, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
21
Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show
Sep 21, 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.