Photo: Keith Pomakis · CC BY-SA 4.0
Oshawa · Canada

Cycling & running events in Oshawa, 2026

125events this year

125 races within 80 km of Oshawa

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

With over 85,000 events in 2026, we have the largest endurance event database on the planet — built to be the fastest way to find a race near you.

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Top events

A few races to know in Oshawa

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
Oshawa

WIN Marathon

Listed in our event index as 2026 Muskoka Marathon.

Road
Bike·Gravel
Oshawa

Hell of the North

Hell of the North is an annual cycling race held at Trail Hub Uxbridge, located at 722 Chalk Lake Road in Uxbridge, Ontario. Participants can select from three routes: the 120 km Hell of the North, the 100 km Sneaky lil Devil, and the 70 km Halfway to Hell. The longest route begins first, followed by the two shorter routes departing thirty minutes later. The series embraces its namesake: the primary race is named "Hell," and the shorter races maintain a similar lighthearted theme. Registration is managed via BikeReg. The event's website provides previous results, photo galleries, frequently asked questions, details about partners, and contact information for participants.

Gravel
Run·Trail
Oshawa

The Whole Enchilada

The Whole Enchilada is a June trail running event held at Trail Hub in Uxbridge, Ontario, northeast of Toronto. Runners begin at 7:30 a.m. Eastern from a Chalk Lake Road venue with direct access to local hiking and biking trails. This event is designed as a Greater Toronto Area trail race, not a road race, with the course focused on the Durham Region’s extensive forest path network. The race takes place within Trail Hub’s 6,000-acre multi-use forest, a region offering over 240 km of hiking and biking trails. Trail Hub currently provides direct access to 8 km of trails, and a gravity-style bike park is planned. The event is organized by a partnership between Trail Hub and Green Newton Adventures, a group dedicated to trail-running and outdoor environmental appreciation. Participants may also link their entry to fundraising efforts, such as supporting the Green Durham Association.

Trail
About cycling & running in Oshawa

Oshawa Training Notes

Running: Locals run Oshawa by linking parks, creek paths, and old race loops. Harmony Creek Path is the easy call, and Harmony Creek Path runs 4K from riverside south to the top of trail. Alexandra Park gives you a simple perimeter when you want steady Z2 without overthinking it. The Waterfront Trail covers 89 km with 11 m of gain. The Waterfront Trail east section runs 97 km with 52 m of gain. The Waterfront Trail west section runs 95 km with 28 m of gain. Seaton Scramble Trail Race is the nearby anchor when you want singletrack, creek crossings, hills, and stairs.

Cycling: Locals ride out of Oshawa on gravel, dirt roads, rail trails, and paved bits near Lake Ontario. Oshawa Cycling Club gives the week structure, with Monday Morning Ride from Courtice Community Center typically running 60 km and Tuesday Evening Ride from Courtice Community Centre ranging from 35/40 km to 60 km. There's an 8 km loop on Osborne Road and Energy Drive. Waterfront Trail, Ritson Rumbler, Harmony Rd N, Stevenson Rd N, and Garrard Gravel and Old Railway Crossing keep base miles honest. Hell of the North sits 23 km away and brings dirt roads, rail trails, and punchy climbs.

Season: Spring gives cyclists the cleanest launch, with Oshawa Cycling Club rides starting in April and gravel rides starting in May. Summer gives Oshawa warm days, Lake Ontario miles, and enough events nearby to keep a calendar full. Fall keeps the running and riding sharp through September and October, especially if you like trail racing and mixed-surface work. Winter turns colder, but Oshawa stays pretty workable by Canadian standards because the city gets one of the lowest yearly snowfall totals in Ontario. Locals shift toward shorter loops, steadier Z2, and whatever path is dry enough to stay fun.

Upcoming

Coming soon in Oshawa

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
Popular elsewhere · next 30 days

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.