Trail Running calendar near Duntroon 2025-2026

Event details The Horseshoe Valley Hustle takes place on October 18, 2025 at Horseshoe Valley Resort in Barrie, Ontario. The event offers three distances: 1KM Small Steps Run/Walk (out-and-back on paved paths) 5KM trail race (one loop) 10K..

Run the Creemore Vertical Challenge on Oct 18, 2025 with looped 14K, 27.5K, 55K or 80K 50 mile options over rolling hills, gravel roads and wooded trails around Mad River Park. Expect steep climbs, scenic views and well stocked aid stations..

Event information The Bolton Rotary Haunted Hill Run is scheduled for October 26, 2025, at 14111 Hwy 50, Bolton, Ontario L7E 1Y6. The event lists 61 participants. Registration opens on September 5 on the event website and is free for all pa..

Get cozy at Chill Session on November 29 in Mulmur with scenic single track trail runs for all levels and a warm hoodie for entrants. Celebrate afterward with chili, beer and s'mores while supporting local food banks.

On April 11, 2026 the Caledon Crusher at Mono Centre is a scenic but savage trail across the Caledon Hills with 25k, 50k and 72k options on technical singletrack and big climbs. Ideal for runners craving a tough, beautiful challenge.

Falling Water Trail Marathon/ Half Marathon 2026 is a rugged trail event on the Beaver Valley section of the Bruce Trail in Eugenia, Ontario. It offers a Trail Marathon (~42km) and a Trail Half Marathon (~21km), each limited to 100 runners...

Timber24 is a 24 hour trail running festival near Barrie where teams of eight or four run an 8 km lap each hour to tackle 192 km together. Camp onsite, refuel with round the clock food and enjoy a Saturday night beer garden.

Event overview The Devil's Key takes place on August 22, 2026 at Devil's Glen Country Club, Simcoe County Road 124, Duntroon, Ontario. The event is sanctioned by Athletics Ontario and supports the Blue Mountains Bruce Trail Club; $20 from e..