Trail Running calendar near Preston Centre 2026-2027

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.

Join Cambridge Ontario's longest trail race with distances ranging from 12.5 km to 50 km and a 12 hour endurance challenge. Enjoy a community atmosphere at Shades Mills Conservation Area with solo and relay options.

A chip timed 4 km on Cambridge’s Mill Run Trail on May 16, 2026. The certified crushed gravel course is an out and back with parking at Riverside Park and reusable chip timing.

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.

Experience the beauty of Crawford Lake Conservation Area with trail races ranging from 1 km to 18.4 km. Run through historic grounds featuring reconstructed Indigenous Longhouses in this professional cup free event.

A fundraising event by CMHA Peel Dufferin in Caledon East on June 7, 2026, offering 25 to 100 km cycling routes and 5 km/10 km trail options for adults and children, with event items and fundraising for mental health services.

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.

A 5 kilometre obstacle run at Victoria Park in Kitchener on July 11 2026 with more than 25 obstacles and 2.5 million cubic feet of foam. The event includes a free kids fun zone, live DJ, food vendors and a licensed beer garden.

Six days, six stages and 60 kilometres in the Conestogo and Waterloo area. A staged event across road, trail, cross country and track with capped registration and time limits.

Join the fourth race of the 5 Peaks Ontario West Series at the Area 8 Conservation Area. Experience trail running in Milton while supporting local charitable foundations.

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

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..

Raid the City 2026 is a team event organized by DontGetLost Adventure Running with online registration via Zone4. Fees are $150 for adult teams and $50 for junior or family teams and deadlines apply.