GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
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Past Events
Sep
2
Wednesday Night Cruise at Orem’s Diner
Sep 2, 2026 · Wilton, CT
Regular cars and coffee / cruise-in gathering in Wilton, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
2
Wednesday Night Cruise at Fritz’s
Sep 2, 2026 · Oxford, CT
Regular cars and coffee / cruise-in gathering in Oxford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
2
THOMPSON ROD AND GUN CLUB CAR CRUISE
Sep 2, 2026 · Thompson, CT
Car show in Thompson, CT, featuring classic, custom, and collector vehicles on display.
Sep
2
29th Annual Cruise Night on Main Street
Sep 2, 2026 · MIDDLETOWN, CT
Regular cars and coffee / cruise-in gathering in MIDDLETOWN, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
2
Cruise Nights at the Knights Council 50
Sep 2, 2026 · Enfield, CT
Regular cars and coffee / cruise-in gathering in Enfield, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
2
Da Andrea Restaurant Classic Car Cruise
Sep 2, 2026 · Westbrook, CT
Car show in Westbrook, CT, featuring classic, custom, and collector vehicles on display.
Sep
1
Dock34 Cruise Night
Sep 1, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
Cruise Night with Paradice Classic Cruisers
Sep 1, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
2026 Cruise Night At Crown Pizza
Sep 1, 2026 · Trumbull, CT
Regular cars and coffee / cruise-in gathering in Trumbull, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
Joanna's Cruise Night
Sep 1, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
Joanna’s Restaurant Classic Car Shows
Sep 1, 2026 · Somers, CT
Car show in Somers, CT, featuring classic, custom, and collector vehicles on display.
Sep
1
Cruise Night
Sep 1, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
Two-Wheel Tuesdays
Sep 1, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Sep
1
Southington Drive-In Tuesday Night Car Cruise
Sep 1, 2026 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
1
American Italian Civic Club – Car Show Sept 7th
Sep 1, 2026 · Waterbury, CT
Car show in Waterbury, CT, featuring classic, custom, and collector vehicles on display.
Sep
1
Hank’s Dairy Bar Car Cruise on the Lawn
Sep 1, 2026 · Plainfield, CT
Car show in Plainfield, CT, featuring classic, custom, and collector vehicles on display.
Sep
1
CAR CRUISE LIVE MUSIC: PHIL SMITH
Sep 1, 2026 · Plainfield, CT
Regular cars and coffee / cruise-in gathering in Plainfield, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
31
Connecticut Valley Brewing Company Cruise Night
Aug 31, 2026 · South Windsor, CT
Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
31
Paradice Classic Cruisers Cruise-In
Aug 31, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Aug
30
British Wheels on the Green
Aug 30, 2026 · Kent, CT
Car show in Kent, 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.