Cruisin’ On First
-by-
Orangeville Cruise Nights
Wednesday, May 20, 2026 at 5:00PM - 8:30PM
Orangeville, Ontario
Weather Timeline
3:00PM
17°C
Clear
Rain 17%
Wind 11 km/h
4:00PM
17°C
Clear
Rain 19%
Wind 12 km/h
5:00PM
17°C
Clear
Rain 20%
Wind 12 km/h
6:00PM
16°C
Clear
Rain 21%
Wind 11 km/h
7:00PM
14°C
Clear
Rain 22%
Wind 10 km/h
8:00PM
13°C
Clear
Rain 23%
Wind 9 km/h
9:00PM
11°C
Partly Cloudy
Rain 23%
Wind 9 km/h
10:00PM
10°C
Partly Cloudy
Rain 23%
Wind 9 km/h
Cruisin’ On First returns for the 2026 season in downtown Orangeville, bringing weekly themed cruise nights all summer long. This long-running series features classic cars, themed nights, and special events that highlight different eras, makes, and styles while keeping the downtown core full of cars and community. 2026 schedule highlights: • May 20 — Opening Night • Weekly themed cruise nights including: * Fabulous 50s, Swingin’ 60s, Sensational 70s, Totally Rad 80s * Classic GM Night, Mopar Mania, Mustang Rodeo & Classic Ford Night * Canadian-Made Classics, Muscle Car Mania, Cruisin’ Corvettes * British Invasion & European/Import Night * Classic Chrome, Fabulous Fins, Classic Truck Round-Up Special events: • June 5 — Orangeville Blues Cruise (Broadway) • July 18 — Orangeville Ribfest Car Show (Alder St. Arena) • September 5 — Orangeville Fall Fair Car Show (Fairgrounds) Other features include youth judging nights and enthusiast spotlight events. Season runs through September 30 with the final cruise night of the year. A staple Ontario cruise series — perfect for regular weekly meets, themed nights, and a strong community turnout all summer long.
