Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 106 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
Trail race at Camp Heidelberg in Waterloo with 2.5 km loops offering distances from 5 km to 50 km, a 6 hour option and a relay; proceeds support Run-Walk-Roll for WRHNCC.
Head for the Hills is an October trail event with 5k and 10k races, a 1k kids run and a 1k Survivor walk supporting the Brain Injury Association of Niagara.
Three trail races in Wawa, Ontario over a weekend offering 6 km, 1.5 km hill climb and 22 km distances with single and combined entry options.
Charity trail event in Vaughan on October 18, 2026 featuring 10K, 5K and 2K distances supporting SickKids and student scholarships.
Community races on Waterford trails with 2 km, 6.5 km and 13 km options plus a Halloween costume contest and prize draws.
A community run and walk at Pinery Provincial Park on October 18, 2026 raising funds for The Friends of Pinery Park across multiple distances.
A vineyard 5K obstacle course at Mastronardi Estate Winery on October 18, 2026 with wine offered along the route and a portion of proceeds to Ronald McDonald House Southwestern Ontario.
Evening trail races on the Maitland Trail in Auburn with 7.21 km and 12 km distances; the course is run in darkness so participants should bring a headlamp.
Point-to-point trail race on October 24, 2026 along the Iroquoia section of the Bruce Trail with 10 km and 25 km options finishing at Dundas Valley Conservation Area.
Point to point trail race on the Maitland Trail with 50K and 25K options, 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.
Trail running on October 25, 2026 with 5 km, 10 km and a 1.5 km kids race, costume contest and donations collected for the Sharing Place.
Raid the Hammer is a point to point adventure run in Waterdown featuring trail running and navigation for teams of two or three.
A cross-country meet at Sunnybrook Park in Toronto offering 6 km and 8 km looped races, open to athletes with or without provincial membership.
Community trail races in Ottawa offering 5K and 10K courses at Wesley Clover Parks with net proceeds supporting the Ottawa Cancer Foundation.
A noncompetitive endurance day on a flat 4 km forest loop in The Blue Mountains where participants choose six or twelve hours and cover as much distance as they wish.
Trail races and an 8 hour endurance challenge at Horseshoe Valley Resort on October 31, 2026 with family 1 km, 5 km, 10 km and team relay options.
A Halloween themed community run in Waterloo offering a 5K, a 200 m fun run, stroller registration, and a pre-race costume contest.