GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
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Upcoming Events
Sep
27
Danbury Auto Spring and Welding Cruize Nights
Sep 27, 2026 · Danbury, CT
Car show in Danbury, CT, featuring classic, custom, and collector vehicles on display.
Sep
27
42nd Annual All Pontiac and Oakland and GMC Fall Car Show
Sep 27, 2026 · Wallingford, CT
Car show in Wallingford, CT, featuring classic, custom, and collector vehicles on display.
Sep
27
September to Remember Car Show
Sep 27, 2026 · 10 AM – 1 PM · Middlefield, CT
September to Remember Car Show at Powder Ridge Mountain Park & Resort, 99 Powder Hill Road in Middlefield, benefits CAFAF's Children's Hope Fund. Show-car entry is $10 cash and spectator admission is free.
Sep
27
42nd Annual Fall Car Show
Sep 27, 2026 · Wallingford, CT
Car show in Wallingford, CT, featuring classic, custom, and collector vehicles on display.
Sep
27
Blood Sweat and Gears Cars and Coffee
Sep 27, 2026 · Milford, CT
Regular cars and coffee / cruise-in gathering in Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
27
Cafaf Car Show
Sep 27, 2026 · Middlefield, CT
Car show in Middlefield, CT, featuring classic, custom, and collector vehicles on display.
Sep
27
4th Annual Third Church Car Show
Sep 27, 2026 · 10 AM – 2:30 PM · Middletown, CT
Third Congregational Church presents its 4th Annual Car Show at 94 Miner Street in Middletown. Vehicle entry is $10 and the show features approximately 30 trophies along with food, music and raffles. Rain date is October 4.
Sep
29
Hank’s Dairy Bar Car Cruise on the Lawn
Sep 29, 2026 · Plainfield, CT
Car show in Plainfield, CT, featuring classic, custom, and collector vehicles on display.
Sep
29
Dock34 Cruise Night
Sep 29, 2026 · Seymour, CT
Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
29
Cruise Night with Paradice Classic Cruisers
Sep 29, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
29
Litchfield Crossings Tuesday Cruise
Sep 29, 2026 · New Milford, CT
Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
29
2026 Cruise Night At Crown Pizza
Sep 29, 2026 · Trumbull, CT
Regular cars and coffee / cruise-in gathering in Trumbull, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
29
Southington Drive-In Tuesday Night Car Cruise
Sep 29, 2026 · SOUTHINGTON, CT
Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
29
Two-Wheel Tuesdays
Sep 29, 2026 · South Windsor, CT
Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.
Sep
29
Cruise Night
Sep 29, 2026 · Somers, CT
Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
30
THOMPSON ROD AND GUN CLUB CAR CRUISE
Sep 30, 2026 · Thompson, CT
Car show in Thompson, CT, featuring classic, custom, and collector vehicles on display.
Sep
30
Wednesday Night Cruise at Orem’s Diner
Sep 30, 2026 · Wilton, CT
Regular cars and coffee / cruise-in gathering in Wilton, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
30
Wednesday Night Cruise at Fritz’s
Sep 30, 2026 · Oxford, CT
Regular cars and coffee / cruise-in gathering in Oxford, CT, drawing classic cars, hot rods, and collector vehicles.
Sep
30
Car show @ Beer Garden @ Bart’s
Sep 30, 2026 · Windsor, CT
Car show in Windsor, CT, featuring classic, custom, and collector vehicles on display.
Sep
30
Cruise Nights at the Knights Council 50
Sep 30, 2026 · Enfield, CT
Regular cars and coffee / cruise-in gathering in Enfield, CT, drawing classic cars, hot rods, and collector vehicles.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.