Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 83 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 races and an 8 hour endurance and team relay at Horseshoe Valley Resort on October 31, 2026, with 1 km, 5 km, 10 km and multi-lap challenges.
Halloween-themed running event in Waterloo featuring a 5K out and back course, a 200 m fun run, a costume contest, and finisher medals for all.
A prediction trail race in Cornwall on October 31, 2026 offering multiple distances, costume and prediction prizes, strict no timing device rules, and post race seasonal treats.
November 2026
Orienteering on a new map at Guidon Park beside the St. Lawrence River in Cornwall, with courses from novice to advanced and a short 15 minute intro clinic.
Trail running at Kamview Chalet in Thunder Bay with on site cash registration and no official timing.
Trail races at Hilton Falls on November 7 2026 offering 10 km, 25 km, and 50 km courses with technical singletrack, aid stations, and finisher medals.
A memorial trail run in Lions Valley on November 7, 2026 with 5 km and 11 km routes, raising funds for Wounded Warriors Canada.
Community 5 km and 1.1 km runs at Riverside Park on November 7, 2026, certified 5 KM, medals for finishers and fundraising for The Preston Legion Poppy Fund.
A canicross and running event at Christie Lake Conservation Area on November 7, 2026 raising funds for Hamilton Animal Services.
Trail races and walks at White Meadow Farms with 10 km and 5 km options plus a 1 km kids run, with proceeds benefiting the Brain Injury Association of Niagara.
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 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.
Fundraising climb up the CN Tower's 1,776 steps on November 14 and 15, 2026 to support United Way work in 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.
Multiple distance trail event at Batawa Ski Hill with aid stations, a cupless policy, sustainable participant medals, and transfers allowed until October 31.
Ontario provincial cross country championships at Malden Park in Windsor on November 15 2026 with age-group races from U8 to Masters and a published technical package.
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.
A community relay over 24 hours in Stratford where participants run or walk a 2 km loop each hour to raise funds for Shelterlink Youth Services.
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
A festive 5k canicross and trail run or walk plus a 1k Elf Run at Kortright Centre, with prizes, post-race treats and fundraising for the Daily Bread Food Bank.