Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 87 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 running at Hardwood on October 25 2026 with 1.5 km kids race plus 5 km and 10 km options, a costume contest, awards and a charity collection.
Teams take part in a point-to-point adventure in Waterdown combining road and trail running, navigation and trekking on 10 to 25 km courses.
Cross country races at Sunnybrook Park on October 25, 2026 offering 6 km and 8 km distances, open entry with non refundable fees.
Community trail race at Wesley Clover Parks on October 25, 2026 offering 5K and 10K loops with net proceeds donated to the Ottawa Cancer Foundation.
Trail races at Horseshoe Valley Resort on October 31, 2026, from a 1 km family dash to a solo or team eight hour endurance challenge.
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.
The 18th annual RememberRun at Riverside Park features a certified 5 km and a 1.1 km fun run with 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 November 14 2026, a daytime Kick-Start and an evening Starry Night, with separate O-CUP points and limited race day registration.
Multiple distance trail event at Batawa Ski Hill with aid stations, a cupless policy, sustainable participant medals, and transfers allowed until October 31.