Trail Running calendar near Shelburne 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..

Run the Wise Raven Trail Race on October 18 at Camp Heidelberg, looping a 2.5 km forest course with rolling hills and some technical sections. Limited to 115 spots, all finishers get medals and excess funds support Run Walk Roll.

Hike 4 Horses is a fundraising community event held at Sunrise Therapeutic Riding & Learning Centre in Puslinch, Ontario. The event offers two 5 km options: a Leisurely Hike and a Timed Run, inviting participants of varying paces to join th..

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 Trick or Trot 2025 is a Halloween-themed run on Saturday, October 25, 2025, at Laurel Creek Trail. The meeting area is listed as 445 Wes Graham Way, Waterloo, ON N2L 6R2. The event programme includes a costume contest at the..

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..

Enjoy scenic trails at the Beav Trail Race in Milton Ontario with 10, 25 and 50 km options around a reservoir and waterfall. Friendly aid stations, custom finisher medals and hoodies for longer distances.

Join the inaugural Oakville Remembrance Trail Run on Nov 9, 2025 for an 11 km route in Lions Valley to honour veterans, service members and first responders. Proceeds support Wounded Warriors Canada; please bring a reusable water bottle.

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.

Pick Your Poison is an April trail ultra near Barrie offering 12.5k, 25k or 50k on a rugged 12.5k loop through forested climbs and spring conditions. Enjoy stocked aid stations, boxed post race food and a fun community vibe.

Event overview Tails on Trails 2026 is a community fundraising event on Sat, May 30, 2026 at Bechtel Park, Bridge Street West, Waterloo, ON, Canada. The event supports the Humane Society of Kitchener-Waterloo and Stratford Perth. The fundra..

The ENDURrun Prelim is a six-day endurance challenge totaling 60 km in Ontario, Canada. The event begins with a prologue at Weberlyn Crescent, Conestogo, and features stages across Waterloo, Cambridge, and Wilmot (RIM Park, Riverbluffs Park..

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...

Take on 80 km over eight stages across the scenic Waterloo region in the annual ENDURrun Sport. Limited to 75 spots, the race includes a tech shirt, finisher medal, course support and varied trail track and road running.

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..

Event overview Kitchener Kids with Cancer 2026 is a fundraising run held on Saturday, September 19, 2026, at Kiwanis Park, 1000 Kiwanis Park Drive, Kitchener, Ontario. The event marks its 13th anniversary and supports the Pediatric Oncology..