Trail Running calendar near Caledon 2025-2026

Join Kitchener Kids with Cancer on Sept 19, 2026 at Kiwanis Park for 5K and 10K looped trail runs supporting the Pediatric Oncology Group of Ontario. All finishers earn a medal and the first 700 registrants receive a technical event shirt.

Blue Bully Ultra is a three day stage trail race at Blue Mountain Resort, Sept 25 to 27, 2026, with Big Bully and Little Bully options. Take on a vertical opener, a long cross country stage and a timed loop finale with on course support.

Run the Heart Lake stop of the 5 Peaks Ontario Trail Running Series on Saturday October 3, enjoying shaded trails, fall colours and lake views. Choose distances from a kids run to longer challenge and soak up a friendly trail race vibe.

Run Sticks n' Stones at Christie Lake on runnable 5.3 km loops with distances from 5 km up to 53 km solo or relay. Proceeds support Oceana Canada, La Sportiva will host a demo and giveaway, and finishers receive a medal.

Creemore Vertical Challenge on October 17, 2026 offers 14K, 27.5K, 55K and 80K 50 mile looped courses with hefty vertical gain per lap. Enjoy scenic gravel roads and trails, stocked aid stations, race swag and free event photos.

Tackle the Lost Valley Trail Race on the Iroquoia section of the Bruce Trail between Burlington and Dundas, with 10 km and scenic but rugged 25 km options. Limited to 180 runners, the course offers rocky single track, escarpment views and s..

Run scenic, mostly fast trails at Hilton Falls with 10 km, 25 km and 50 km distances to suit every trail runner. Enjoy a few technical sections, a waterfall pin, on course s'mores, La Sportiva shoe demos and finisher swag.