Trail Running calendar near Waterloo 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.

Trail race at Wildwood Conservation Area with day and night options and distances of 10 km, 25 km and 50 km. The course features lake views, variable terrain, staffed aid stations and required lighting, with proceeds supporting Ontario Natu..

A multi‑distance trail running event at Kelso Conservation Area on May 2, 2026, with courses from a free 1 km kids event to a 21 km Grit race. Multiple categories and variable fees, plus fundraising options.

Trail race in Cambridge Ontario on May 9, 2026 offering 12.5 km, 25 km, 50 km, a 12 hour event and a team relay. Races use repeated 6.25 km loops and the event includes fundraising for KidsAbility.

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.

A fundraising trail event at Bechtel Park offering 5K and 2.5K options with or without dogs plus a 200 m Pup Run. Fundraising tiers unlock event apparel and swag.

A 100 miles route circling the City of Hamilton through six communities. Finish within 40 hours for a Gold buckle or complete the distance during June to receive a Pewter buckle.

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.

A 15 hour 23 minute looped trail event on an approx. 3.7 km circuit at Marydale Park with a relay option for teams up to five, a single aid station per lap, and proceeds supporting the C.Y.O. One-to-One camp program.

A timed event in London, Ontario where all runners start together and try to get as far as possible from the common start within set times. Winners are those farthest away as the crow flies.

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 5K obstacle event at Victoria Park in Kitchener on July 11, 2026, featuring 25+ obstacles and 2.5 million cubic feet of foam. Festival features include a free kids zone, live DJ, food vendors and a licensed beer garden.

Trail races on the Toronto Bruce Trail near Milton Ontario with about 52 km, 27.5 km and 10 km options. Point-to-point courses use white blazes, include shuttle service and spaced aid stations.

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.

A foam filled 5K at Boler Mountain on July 25, 2026 featuring 25 plus obstacles and about 2.5 million cubic feet of foam. The event includes a family festival area with a free Kids Fun Zone, live DJ and food vendors.

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