Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 93 exciting trail runs across the region. Find your next trail run in Ontario below and join the trail community at these great events!
October 2026
Free weekly stair-climbing sessions at the top of the Kenilworth Stairs in Hamilton, organized by Coach B and the Squad, with optional post-workout chocolate shakes for purchase.
Obstacle course weekend at Blue Mountain Ski Resort on Oct 17 to 18, 2026 with Sprint 5 km, Super 10 km, Beast 21 km and kids races; complete all three to earn the Trifecta Medal.
Trail races at Fanshawe Conservation Area offering 25k single loop and 50k two loop options around the reservoir with on course support and a finisher medal.
Trail event at Long Sault Conservation Area with 2K kids, 7K, 14K, 21K and a six hour looped race plus one aid station and paid parking.
A multi-distance trail and gravel event around Creemore offering 14K to 80K options with aid stations, drop bag service, and event swag in October 2026.
Trail loops at Camp Heidelberg in Waterloo on October 17, 2026 offering 5 km to 50 km distances plus timed six hour options.
Three trail races in Wawa, Ontario on October 17 and 18, 2026, offering 6 km, 1.5 km hill climb and 22 km options with single and combo fees.
Championship orienteering in Kingston on October 17 to 18, 2026 with mapped middle, night, and long races plus recreational and age-class courses.
Charity run in Vaughan offering 10K and 5K trail races plus a 2K family run, supporting SickKids and scholarships with race-day amenities.
Community races on Waterford trails with 2 km, 6.5 km and 13 km options plus a Halloween costume contest and prize draws.
A fundraising run and walk at Pinery Provincial Park on October 18, 2026 with multiple distances, trail sections, wheelchair entries, and participant awards supporting park projects.
A 5K obstacle course through Mastronardi Estate Winery in Kingsville ON on October 18, 2026, with wine served at each kilometre and professional timing by W.R.A.C.E.
Nighttime trail races of 7.21 km and 12 km along the Maitland Trail at Auburn Riverside Retreat on October 23, 2026; a headlamp is required.
Point-to-point trail races of 10 km and 25 km finishing at Dundas Valley Conservation Area, with bus transport to starts, aid stations, and race kit items included.
Point to point trail race on the Maitland Trail in Ontario with 50K and 25K routes, technical single track terrain, mandatory bus transfer, and post race food and swag.
A non-competitive 5 km run in Masaryktown Scarborough with on-site race packs and a republic shaped finish medal.
Nighttime cyclocross-style running at Christie Pits Park with three heats including a 6 km cash race and a 3 km beer lap with prizes.
A timed, in person endurance day on a flat 4 km forest loop with six or twelve hour options, limited to 18 participants and supported on course.
Trail running at Hardwood on October 25 2026 with 1.5 km kids race plus 5 km and 10 km options, a costume contest, awards and a charity collection.