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
Thanksgiving Monday community run on October 12, 2026, with 1K, 2.5K and 5K options, a Golden Drumstick prize and finisher medals.
Turkey Trot at Springbank Park on October 12, 2026 offers 6.5 km, 2 km and a Kiddy Trot, with donations collected for the London Food Bank.
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 races at Long Sault Conservation Area include 2K, 7K, 14K, 21K and a 6 hour loop event on two 7 km trail loops.
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 race at Camp Heidelberg with repeated 2.5 km loops, multiple distance options, electronic timing and proceeds benefiting Run Walk Roll for WRHNCC.
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 charitable run and walk at Pinery Provincial Park on October 18 2026 offering multiple distances, chip timing, wheelchair divisions, and fundraising for The Friends of Pinery Park.
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.
Night trail races of 7.21 km and 12 km on the Maitland Trail near Auburn Ontario with check in at Auburn Riverside Retreat; registrations are sold out.
Point-to-point trail races of 10 km and 25 km along the Bruce Trail, finishing at Dundas Valley Conservation Area with aid stations and included race kit items.
Point to point trail race on the Maitland Trail in Huron County with 50K and 25K options, technical single track, mandatory bus transfer and a catered post race meal.
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.