Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 119 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
Community run and roll on October 18, 2026 with 2 km, 6.5 km and 13 km routes, a costume contest with gift card prizes, required pre registration and finish line refreshments.
Fundraising run and walk on October 18 2026 at Pinery Provincial Park offering multiple distances, chip timing, and support for park projects.
A 5K obstacle course at Mastronardi Estate Winery in Kingsville on October 18, 2026, featuring wine at each kilometre, official timing, and proceeds to Ronald McDonald House.
Night time trail race on the Maitland Trail near Auburn Ontario, offering 7.21 km and 12 km options; registration opened May 1, 2026.
Point to point trail races on the Iroquoia Section of the Bruce Trail offering 10 km and 25 km courses finishing at Dundas Valley Conservation Area with limited entries.
Point to point 25 km and 50 km trail races along the Maitland Trail finishing at Auburn Riverside Retreat with mandatory bus transfer to the starts.
A non-competitive 5 km run in Masaryktown Scarborough with on-site race packs and a republic shaped finish medal.
Trail event on October 25, 2026 featuring kids and 5 km and 10 km races, a costume contest and donations for the Sharing Place.
Team-based adventure run in Waterdown combining road, trail, navigation and trekking with Raid (20–25 km) and Half-Raid (10–15 km) options.
Trail races and an 8 hour endurance challenge at Horseshoe Valley Resort on October 31, 2026, featuring a 5 km loop, aid station and resort amenities.
Halloween themed running event in Waterloo Ontario with a 5K, a 200 m fun run, a pre race costume contest, and medals for all participants.
November 2026
Trail running event in Thunder Bay on November 3, 2026 with start and finish at the Kamview Chalet. Cash payment on site with a 10 USD per person fee and a 30 USD family maximum. The event is not timed.
Trail races of 10 km, 25 km and 50 km at Hilton Falls on November 7, 2026 with technical sections, aid stations and a 9 hour cutoff for the 50 km.
A November 7, 2026 trail event in Lions Valley offering 11 km and 5 km routes to honour veterans and support Wounded Warriors Canada. Registration opens spring 2026.
Canicross races, human runs and a fun walk at Christie Lake to raise funds for Hamilton Animal Services adoption programs.
Trail event at Batawa Ski Hill on November 15, 2026, offering distances from a 1 km kids run to a 50 km with stocked aid stations and a cupless policy.
Trail event at Mansfield Outdoor Centre offering 10 km, 5 km and a 1 km kids race, with hoodies, medals, chili and beer for adult distances. Cup free, on course aid and meals in the cafe, registration closes November 1 2026.
December 2026
Winter trail event at Marydale Park offering timed Solstice formats with aid stations, finisher medal, crewneck and charity support.
January 2027
Night snowshoe race through Upper Canada Village's illuminated heritage buildings with 5 km loops and fundraising for the WDMH Family Care Fund.