Trail Running calendar near Milton 2026-2027

The 13th annual Kitchener Kids with Cancer run supports the Pediatric Oncology Group of Ontario. Choose from a 5k, 10k, or walk on the trails of Kiwanis Park. Registration includes a t-shirt and finisher medal, with post-race food and festi..

An urban trail race exploring Hamilton's forests, creeks, and iconic waterfalls. Choose from four distances, from a gentle 5k to a rugged 21k on the Bruce Trail. The event is transit-friendly, features a unique toque for runners, and emphas..

A 5k trail run through the scenic fields of the Donkey Sanctuary of Canada in Puslinch. A 1k route is also available. This fundraising event takes place on September 27, 2026.

The fifth race in the 5 Peaks Ontario Trail Running Series takes place at Heart Lake Conservation Park. Runners can choose from four distances on shaded trails famous for autumn colours. The event offers free parking and follows a cup free..

This trail race at Christie Lake Conservation Area offers multiple distances on a 5.3 km looped course. Participants receive a souvenir item and a finisher's medal. The event supports Oceana Canada.

Tackle a scenic 2.5km forest loop at Camp Heidelberg. Choose from five solo distances or a team relay. This Athletics Ontario sanctioned event supports a charitable cause with any surplus funds.

The Lost Valley Trail Race is a point-to-point adventure on Ontario's iconic Bruce Trail. Choose between a 10 km or 25 km journey, both finishing at Dundas Valley Conservation Area. The event includes bus transport, a finisher's medal, and..

The Beav Trail Race at Hilton Falls on October 31 offers 10 km, 25 km and 50 km on fast but technical trails with scenic waterfall views. Bring your own cup or bottle as no cups are provided, and finishers earn a custom medal and apparel.

A unique trail race timed to the winter solstice. Choose your challenge: 8h58, 4h29, 2h15, or as a relay on a 3.7 km loop. A finisher's medal, sweatshirt, and warm vibe await.