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Windsor · Canada

Cycling & running events in Windsor, 2026

30events this year

30 races within 80 km of Windsor

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A few races to know in Windsor

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Windsor

Ciociaro Race Series

The Ciociaro Race Series is a weekly cycling event held on a closed circuit at the Ciociaro Club in South Windsor, Ontario. It takes place during the warmer months of the local racing season, with evening races at the club grounds in Oldcastle. Participants are divided into A, B, and C categories, with each group starting separately to accommodate different speeds and experience levels. The course utilizes the club’s circuit, offering a consistent format each week. Standings are based on points, emphasizing regular participation alongside individual performance. Riders can also compete for cash primes during the races. The series maintains a relaxed local atmosphere, including pizza. Now in its second decade, the event is listed on the Ontario Cycling calendar as a recurring club-style race night.

Road
Run·Road
Windsor

Moon in June

Moon in June is a 5 km run and walk held in Windsor, Ontario, beginning and ending at the Windsor Family Credit Union Centre. The event also offers children's races: a 1 km kids' event and a 200 m dash. The main 5 km race uses chip timing, and children receive race bibs appropriate for their events, accommodating both timed runners and families seeking a shorter distance. Part of the route follows the Ganatchio Trail in the Little River Corridor, featuring a shared two-way section; running strollers and dogs are not permitted. Registration provides a limited-edition Moon in June item, a finisher medal, race photos, and post-race refreshments from Tim Hortons, Capri Pizzeria, Pure Flavor, and Hyena Brew Company. Awards are presented to the top three overall male and female finishers, and the first-place finisher in each age group. The event supports the We Care for Kids Foundation, with participants able to have their entry fee waived by collecting $200 in pledges.

Road
Run·Road
Windsor

Pedals and Passport

Pedals and Passport is a cross-border cycling event from the Detroit area into Windsor, Ontario. It is the signature ride of Metro 313 Cyclones Major Taylor Detroit. Its central hook is in the name: riders need a passport or a valid enhanced driver's license as the route crosses from the United States into Canada. The event offers three route options, plus a Metro Detroit ride for those who want to stay on the Michigan side. The Canadian routes start and end at Malden Park, then follow mostly flat, smooth roads toward Amherstburg, Colchester, and Leamington. Riders reach Windsor by using either the Ambassador Bridge or the Detroit-Canada Tunnel, then spend the day near the Detroit River, farmland with wind turbines, wine country, and Lake Erie overlooks. Part of the route passes through communities tied to the northern end of the Underground Railroad, adding a piece of borderland history to this international bike ride.

Road
About cycling & running in Windsor

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.

Upcoming

Coming soon in Windsor

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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What runners & riders are signing up for

If you're traveling — or just curious — here's where the action is across two of the most active markets on TrainerDay.