Trail Running calendar near Oakville 2026-2027

Experience a fast and traffic free 5km race along the scenic Hamilton waterfront trail. This event features a flat course at Bayfront Park with chip timing, custom medals, and post race hot food for all participants.

Experience a technical trail run through the scenic Caledon Hills Bruce Trail with choices of 25 km, 50 km, or a full 72 km traverse ending at Mono Centre.

Experience one of the fastest trail races in Canada on the flat and groomed paths of Dundas Valley. Choose from distances between 5 km and 50 km in this scenic community event.

Explore the scenic and technical trails of Kelso Conservation Area with distances ranging from 1 km to 20.6 km. This cup free trail event offers a unique outdoor challenge for runners and hikers of all ambitions.

Explore the scenic Seaton Trail in Pickering with distances from 1 km to 50 km. Enjoy a course featuring creek crossings, stairs, and hills with options for both trail runners and hikers.

A historic looped trail race in the Dundas Valley, offering distances from 10k to 100 miles. Features a hilly 20k loop, is a cup free event, and a Western States qualifier. Canada's oldest ultra trail race.

Support the local Humane Society at Bechtel Park by participating in a timed 5 km trail race or untimed 2.5 km and 200 m runs with or without your dog.

Test your limits on the single track trails of Dufferin County Forest with distances ranging from 5 km to a 100 km ultramarathon available for solo runners and relay teams.

Circumnavigate the City of Hamilton in this 100 mile challenge through six diverse communities. Choose between a continuous 40 hour ultra or complete the distance in stages throughout the month.

The 5 Peaks Trail Running Series comes to Crawford Lake in June 2026. This trail run takes place at the Crawford Lake Conservation Area in Milton. Swag is optional and park fees may apply.

The 38th annual trail half marathon and 7k takes place in St. Catharines. The historic half marathon course follows the first Welland Canal and descends the Niagara Escarpment. Participation is capped and the event supports the Niagara Rank..

Join Hope in Motion 2026 in Caledon East for a day of cycling, running, and walking to support mental health services. Choose from distances up to 100 km and help make a direct impact in the Peel Dufferin community.

Join the fifth annual Rainbow Trail Run at Earl Rowe Provincial Park featuring scenic lake loops from 6 km to 62 km on a beginner friendly trail course.

Experience a unique endurance challenge during the longest day of the year at Marydale Park. Run solo or as a relay team for over 15 hours on a scenic 3.7 km trail loop.

Trail running event at Kelso Conservation on June 27, 2026 offering 2K, 5K, 10K, MAX Elevation and a 20K relay. Courses include aid stations, professional chip timing and a post event village with awards.

A 5 km fun run obstacle course at Victoria Park in Kitchener. Features over 25 obstacles including foam, slides, and mud pits, all optional. The event includes a festival area, fundraising, and a free kids zone.

Experience an authentic point to point adventure along the historic white blazes of the Bruce Trail. Navigate technical terrain and stunning conservation areas in this small community focused trail race.

The ENDURrun Prelim is a six-day, six-stage challenge totalling 60 km. It blends road, trail, cross-country, and track racing on varied courses across Ontario. A complete test of endurance with a finisher's medal and technical shirt for all..

Run a 7 km loop through the Carolinian forest of Dundas Valley. Choose from distances ranging from a single loop to a 100-mile ultra or the unique "Gong Show" elimination race. All finishers get a medal, and early registrants receive a race..

The ENDURrun is the ultimate test of endurance: 160 km across seven stages over eight days in August 2026. The challenge includes a half marathon, cross country, marathon, and time trials. Relay team and individual stage guest options are a..