Trail Running calendar near Waterloo 2026-2027

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.

Experience the thrill of trail running by day or night at Wildwood Conservation Area with 10 km, 25 km, and 50 km races featuring fast tracks and muddy turns.

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.

Experience Ontario oldest ultra trail event in the scenic Dundas Valley. Run through Carolinian forests on a challenging multi loop course with distances ranging from 10 km to a WSER qualifying 100 mile solo 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.

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.

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.

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.

Experience a unique 5 km fun run featuring over 25 obstacles and massive amounts of foam. Join the festival at Victoria Park on July 11 2026 for mud pits, waterslides, and a free kids zone for the whole family.

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.

Experience a comprehensive 6 day running challenge covering 60 km across diverse terrains in Ontario. Test your limits with daily stages featuring road, trail, track, and cross country disciplines.

Experience a unique 5 km obstacle run at Boler Mountain featuring foam and oversized slides. Open to ages 7 and up with a dedicated kids zone and festival atmosphere for the whole family.

Experience a diverse trail event in Hamilton featuring loop-based distances from 7 km to 100 miles and unique timed elimination challenges.

Test your endurance at Ontario's original affiliated backyard ultra on a flat course in Arva to compete for a Silver Ticket to the World Team Championship.

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..

Trail running at Albion Hills Conservation Park with singletrack trails along the Humber River. Three distance options with maps, aid stations and on site awards; swag and finisher medals available for purchase.

Test your grit at Gopher Dunes with 5 km or 15 km obstacle courses set in rugged Ontario terrain. Enjoy a vibrant festival atmosphere and earn your iconic orange headband alongside your teammates.

Experience a brand new Spartan venue at Gopher Dunes near London Ontario. Challenge yourself with 5K and 10K obstacle courses set across rugged farmland and forest trails.