Trail Running calendar near Alliston 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 details The Trails & Tails Classic takes place on October 19, 2025 at Terra Cotta Conservation Area, 14452 Winston Churchill Blvd, Halton Hills, ON L7G 0N9. The event is organized by Canadian Canicross Sports and had 55 participan..

Event overview The Cider Run is a trail running event held at Slabtown Cider Company / Woodnewton Farm in Uxbridge, Ontario on Saturday, October 25, 2025. The course uses trails on the Oak Ridges Moraine and routes and distances may be chan..

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..

The Beav Trail Race is a multi-distance trail running event held at Hilton Falls Conservation Area near Milton, Ontario, Canada. Distances include 10 km, 25 km, and 50 km, with the 50 km run as two laps of the 25 km course. The 10 km is an..

Oakville Remembrance Trail Run is held at Upper Middle Park in Oakville, Ontario, featuring an 11-kilometer trail course through Lions Valley. Promoted as the first annual event, it aims to honor veterans, first responders, and their famili..

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.

Event overview The Golden Spike Trail Race takes place on December 6, 2025, at Crawford Lake Conservation Area, Conservation Road, Milton, Ontario. The event offers trail running through forest paths and around Crawford Lake, including boar..

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.

The Seaton Scramble Trail Race will take place in Pickering on Saturday 9 May 2026.

The Whole Enchilada is a trail running race held at Trail Hub in Uxbridge, Ontario, in Canada’s trail capital, Durham Region. It offers multiple distances: The Full Enchilada (50 km), Half Enchilada (25 km), Mini Enchilada (8 km), Hike Ench..

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...

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..

The Beav Trail Race 2026 The event takes place on Saturday, October 31, 2026, at Hilton Falls Conservation Area in Milton, Ontario. The event is sanctioned by Athletics Ontario. La Sportiva will provide a demo fleet of shoes and will give a..