GarageCherries

Connecticut Car Shows & Events

Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.

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Narrow the events below by city, ZIP, event type, or date.

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City

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Past Events

Aug

Car Show

State Line Car Show

Aug 26, 2026 · Granby, CT

Car show in Granby, CT, featuring classic, custom, and collector vehicles on display.

Aug

Car Show

Car show @ Beer Garden @ Bart’s

Aug 26, 2026 · Windsor, CT

Car show in Windsor, CT, featuring classic, custom, and collector vehicles on display.

Aug

Cruise Night

Litchfield Crossings Tuesday Cruise

Aug 25, 2026 · New Milford, CT

Regular cars and coffee / cruise-in gathering in New Milford, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Car Show

Two-Wheel Tuesdays

Aug 25, 2026 · South Windsor, CT

Car show in South Windsor, CT, featuring classic, custom, and collector vehicles on display.

Aug

Car Show

Joanna’s Restaurant Classic Car Shows

Aug 25, 2026 · Somers, CT

Car show in Somers, CT, featuring classic, custom, and collector vehicles on display.

Aug

Cruise Night

Southington Drive-In Tuesday Night Car Cruise

Aug 25, 2026 · SOUTHINGTON, CT

Regular cars and coffee / cruise-in gathering in SOUTHINGTON, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Cruise Night

Joanna's Cruise Night

Aug 25, 2026 · Somers, CT

Regular cars and coffee / cruise-in gathering in Somers, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Cruise Night

Dock34 Cruise Night

Aug 25, 2026 · Seymour, CT

Regular cars and coffee / cruise-in gathering in Seymour, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Car Show

Monday Night Cruzin’ Fish Family Farm

Aug 24, 2026 · Bolton, CT

Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.

Aug

Cruise Night

Cruise Night – Open Cruise

Aug 24, 2026 · South Windsor, CT

Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Car Show

Monday Night Cruisn’

Aug 24, 2026 · Bolton, CT

Car show in Bolton, CT, featuring classic, custom, and collector vehicles on display.

Aug

Cruise Night

Cruise Night: Oldsmobile/Buick/Cadillac/Pontiac

Aug 24, 2026 · South Windsor, CT

Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Car Show

Hlobik’s Cars, Trucks & Bikes – Monday Night Car Show

Aug 24, 2026 · Willington, CT

Car show in Willington, CT, featuring classic, custom, and collector vehicles on display.

Aug

Cruise Night

Connecticut Valley Brewing Company Cruise Night

Aug 24, 2026 · South Windsor, CT

Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Cruise Night

Cars and Coffee at the Birdhouse

Aug 23, 2026 · South Windsor, CT

Regular cars and coffee / cruise-in gathering in South Windsor, CT, drawing classic cars, hot rods, and collector vehicles.

Aug

Car Show

6th Annual Legacy Cars, Jeeps & Motorcycles Show

Aug 23, 2026 · Southington, CT

Car show in Southington, CT, featuring classic, custom, and collector vehicles on display.

Aug

Car Show

41st Annual Sock Hop and Car Show

Aug 23, 2026 · Prospect, CT

Car show in Prospect, CT, featuring classic, custom, and collector vehicles on display.

Aug

Car Show

Caffeine & Carburetors (lite)

Aug 23, 2026 · New Canaan, CT

Car show in New Canaan, CT, featuring classic, custom, and collector vehicles on display.

Aug

Car Show

Air-Cooled at the Orchard

Aug 23, 2026 · 9 AM – 3 PM · Middlefield, CT

The Connecticut Volkswagen Association and Connecticut CORSA present Air-Cooled at the Orchard at Lyman Orchards, 32 Reeds Gap Road in Middlefield. The show is open to air-cooled Volkswagens, Porsches and Corvairs. Show-car entry is $10 and spectator admission is free. The event is rain or shine.

Aug

Car Show