Trail Running calendar near Oro Station 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 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..

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 Kawartha Lakes Winter Festival is an inaugural one-day outdoor event on Sunday, February 1, 2026, at Eganridge Resort, Golf Club & Spa in Fenelon Falls, Ontario. The festival is presented by Snowshoe Canada and combin..

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..

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..