Cycling & running events in Windsor, 2026

Windsor Base Miles

Running: Locals run the Riverfront Trail when they want easy views and steady Z2, and the bridge-to-Reaume Park out-and-back gives about 16km round trip beside the Detroit River. The Greenway handles long-run days because the old rail line runs from Highway 3 to Leamington and stacks mileage without drama. Ojibway Complex leads through Spring Garden to the Herb Gray Parkway, while Black Oaks trails can fill 20km just by wandering. The Running Factory list keeps the club scene busy with Blue Heron Blazers, Sandwich Beer Runners, weULTRA, Ford City Runners, Malden Park Runners, Slow Motion Run Club, and more. WINDSOR WATERFRONT HALF MARATHON & 5KM is the anchor event.

Cycling: Locals ride the Riverfront Trail, Ganatchio Trail, Herb Gray Parkway Trail, and the Windsor Loop when they want clean base miles inside the city. The Windsor Loop connects Malden Park, the Gordie Howe International Bridge pathway, the Trans Canada Trail, and about 50km of perimeter riding. 700 Cycling Club rolls Saturday mornings at 08:50 from Alexandra Gardens, usually 40-60km in no-drop groups. The climbs are north and east, where you'll find rolling gravel and the hilly 10 mile bacon strip. Pedals and Passport and Ciociaro Race Series sit on the calendar.

Season: April through October is the easiest stretch because the city has e-scooter and e-bike rentals running, and bikes stay useful for errands, recovery spins, and steady Z2. Summer riding likes the riverfront, Lake St. Clair, and the south peninsula with frequent Lake Erie views, while summer running works best early on weekends for long runs. The flat, unshaded rail lines make heat management matter on Greenway days and Amherstburg to Essex trail days. Winter makes cycling in Windsor challenging, and Ciociaro Race Series days can feel cold and windy. Runners keep the parks, riverfront, and old rail lines in play, while cyclists lean harder on sheltered routes and simpler miles.