GarageCherries
Connecticut Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Connecticut for 2026.
Featured Events
Aug
21
Dream Ride Experience 2026
Aug 21 – Aug 23, 2026 · Farmington, CT
The Dream Ride Experience returns to the Farmington Polo Club, 152 Town Farm Road, for a three-day automotive and charitable celebration. The weekend includes exotic, classic and collector cars, the Saturday Dream Cruise, Sunday's Dream Show and judged car show, motorcycles, live entertainment, family activities and events supporting Special Olympics athletes.
Upcoming Events
Aug
23
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
29
2nd Annual Summertime Classic Car Show
Aug 29, 2026 · 10 AM – 2 PM · West Haven, CT
Surfside Veterans presents the 2nd Annual Summertime Classic Car Show at the West Haven City Hall Community Parking Lot. The fundraiser features classic and enthusiast vehicles, awards, food trucks and vendors. Awards are scheduled for 1 PM.
Sep
19
3rd Annual 1781 Cars on Main
Sep 19, 2026 · 11 AM – 2 PM · Wethersfield, CT
The 3rd Annual 1781 Cars on Main takes place at 250 Main Street in historic Old Wethersfield. The show features an impressive lineup of enthusiast vehicles along a closed section of Main Street with music, food trucks and community activities.
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
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.
Nov
22
Class of 2026 Car Show
Nov 22, 2026 · 12:30 PM · Madison, CT
Class of 2026 fundraising Car Show in the First Citizens Community Bank parking lot in Madison. The show begins at 12:30 PM and includes four vehicle trophies, including specialty awards.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.