Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 115 exciting trail runs across the region. Find your next trail run in Ontario below and join the trail community at these great events!
September 2026
Trail races from 12K to the Haliburton Forest 100 Miler across heavily wooded, hilly trails with lakes and streams on September 12 and 13, 2026 in Haliburton Ontario.
Trail races on the Bruce Peninsula across multiple distances, with Saturday Bruce Trail routes and a Sunday Flowerpot Island 5 km including a boat tour and breakfast.
Races along Lake Nipissing on September 12, 2026: 5k, 10k, 21.1 km and a free 1 mile kids race, with donations to YMCA Fill The Bus.
Obstacle mud run at Gopher Dunes on September 12, 2026 offering 15K and 5K courses, finisher medals, shirts, headbands and a spectator village.
Backyard Ultra at Woodbine Beach Park with 6.71 km loops, an hourly elimination format, a 15-hour endurance option, and a one-Yard community waterfront run.
A survival-style family obstacle challenge in Mississauga for adults, children and dogs at Paramount Fine Foods Centre on September 12, 2026.
Obstacle course races at Gopher Dunes in Courtland ON on September 13 2026 with a 5 km sprint of 20 obstacles and a 10 km super of 25 obstacles.
A chip timed two loop trail 5 km at Bechtel Park in Waterloo on September 13, 2026, with no swag and free entry for Run Waterloo members.
Community run among the vines at Palatine Hills Estate Winery with a timed 5 km race, family fun run and dog walk plus post-run food and live music.
Trail running event in Thunder Bay on September 15, 2026, organized by Thunder Bay Nordic Trails and Fresh Air with proceeds to the Reijo Puiras Legacy Fund.
Guided trail miles, New Balance Hierro v9 demos, and draw prizes at Sulphur Springs, Ancaster, on September 16, with free admission.
A 7 km trail event in Kincardine on September 19, 2026, with start and finish at Station Beach. Runners and walkers can take part and prizes are awarded to children under 12 and the top three finishers in each age category.
Trail races at Bon Echo Provincial Park with 43 km, 30 km, and 10 km options, long backcountry sections, and aid stations providing food and drinks.
An ultrarunning event at Sugarbush Vineyards with a flat 3 km loop and options for 6, 12, 24 hour races plus a 24 hour relay.
Trail races on private Woodnewton Farm trails near Slabtown Cider Co. with multiple distances, kids races, post-race local food and cider, and donations to trail stewardship.
A live and virtual 5K, 10K and 15K run or walk on the Howard Watson Trail supporting Rayjon Share Care with local brewery partners and participant perks.
Cross country races at Fort Henry Hill with a 5 km loop and a kids 1 km race, team divisions, age category medals, and finisher ribbons.
Timed-loop trail event at Kelso Conservation Area on September 19, 2026, with options from a 1 hour 2 km loop to 6 hour relays and a children's race.
Berry Dreams Fun Run at Heeman's in London ON offers 1K kids, 5K and 10K trail runs on September 19 and raises funds for the Shine Foundation.