Cruise Night on Main Street
Wednesday, September 2, 2026 from 4:30-8:00 p.m. on Main St, Middletown!
In collaboration with the City of Middletown, we’ve moved the event to early September to better support our downtown businesses during a summer with frequent Main Street closures, give the classic cars a cooler night to cruise (no overheating!), and complement the many America 250 events happening in Middletown (and our region) this summer.
It’s also the perfect way to celebrate Labor Day weekend and close out the summer together! Join us for classic cars, music, great food, and thousands of spectators lining Main Street for one of Middletown’s favorite traditions. End the summer with us on Main Street!
Hundreds of cars lined both sides of scenic Main Street from Washington Street to the South Green for the 29th annual celebration of classic vehicles on Wednesday, September 2, 2026. Music, food, and an impressive display of pre-2001 classic cars made it a fun, family-friendly event for all. The event benefited Middletown youth programs.
This event was made possible by the support of volunteers.
Special Thanks to: Connecticut Military Corvette Club and Garage Guys Car Club.