Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 82 exciting trail runs across the region. Find your next trail run in Ontario below and join the trail community at these great events!
November 2026
Trail races at Hilton Falls with 10 km, 25 km and 50 km options on mixed groomed and technical trails, supporting MedVents and sanctioned by Athletics Ontario.
A remembrance-focused trail run in Lions Valley on November 7, 2026 offering 11 km and 5 km routes to raise funds for Wounded Warriors Canada.
RememberRun 2026 in Riverside Park, Cambridge features a certified 5 km race and a 1.1 km fun run with pre-race ceremonies and fundraising for the Preston Legion Poppy Fund.
A trail event at Christie Lake pairing runners and dogs to raise funds for Hamilton Animal Services, with canicross, human 5K and 10K, and a 5K fun walk.
Trail races at White Meadow Farms and Short Hills Provincial Park on November 7, 2026 with 10 km, 5 km and 1 km options and proceeds to a local brain injury charity.
Orienteering at Kanata Lakes on November 8, 2026 with novice to advanced courses, a 15-minute intro clinic, advance waiver submission option and on-site registration.
A community-focused outdoor session at Humber River Recreational Trail covering layering, footwear, basic trail running and guided 2.5 km and 5 km routes.
A two hour charity run at Coronation Park on Nov 11 raising funds and winter care donations for Ubuntu’s 2026 Holiday Initiative with 50 prize giveaways.
Climb the CN Tower's 1,776 steps on November 14 and 15, 2026 to raise funds for United Way work across Peel, Toronto and York Region.
Two orienteering races on 14 November 2026 at Breithaupt Park and Bechtel Woods with separate O-CUP points and limited race-day entries.
Trail running at Batawa Ski Hill on November 15, 2026 with multiple distances from a 1 km kids race to a 50 km course, aid stations and handmade medals.
Provincial cross country championships at Malden Park in Windsor on November 15, 2026, featuring U8 to Masters races with individual and team scoring.
Two days of orienteering in the Waterdown area on November 21 and 22, 2026 with a Classic at Mount Nemo, a Sprint at Joe Sams Park and an Ontario Cup at Rockcliffe Trails.
24 hour community relay in Stratford where participants run a 2 km loop each hour to raise funds for Shelterlink Youth Services with a CA$35,000 goal.
Trail runs at Mansfield Outdoor Centre with 10K, 5K and a free 1K kids race; entries include hoodies, medals and postrace chili and beer.
December 2026
Festive 5k canicross and trail run with a 1k Elf Run at Kortright Centre, supporting the Daily Bread Food Bank with post-race treats and awards.
Winter trail race at Marydale Park on December 19, 2026 with full, half, quarter and relay options on an ~3.7 km loop; aid station, medal and crewneck included.
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.
Winter trail races at Long Point Eco Adventures with 5K, 10K and 25K looped courses plus canicross options near Turkey Point on Lake Erie.
A 6.5 km snowshoe race at Cold Creek Conservation Area on January 16, 2026 featuring mixed single-track and wide trails, limited snowshoe rentals, and a 60-participant cap.