Ontario
Trail Running Calendar Ontario 2026-2027
Explore the best trail runs in Ontario for 2026-2027! Our updated list features 80 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
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 50 km, aid stations and participant medals.
Provincial cross country championships at Malden Park in Windsor on November 15, 2026 with published registration tiers, course preview and technical rules.
Repeated one mile loops at Christie Pits Park with shrinking time limits, free entry and limited space; the format removes slower runners as limits tighten.
Two-day orienteering weekend in the Waterdown area on November 21 and 22, 2026 with the Ontario Cup mass start, a sprint at Joe Sams Park and a classic at Mount Nemo.
Trail event at Mansfield Outdoor Centre on November 28, 2026 featuring 10K, 5K and a kids 1K with hoodies, chili, beer and raffles for local food banks.
December 2026
A timed winter solstice trail event at Marydale Park on December 19, 2026 with Full, Half, Quarter and relay options, aid station service, and finisher gear.
January 2027
Night snowshoe races through Upper Canada Village lights with 5 km and 10 km options, headlamps required, limited rentals and a 180 participant cap.
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 in Nobleton with limited entries, snowshoe rentals, post-race chili and an awards presentation.
A 6.5K single-loop snowshoe race at Goodrich Loomis Conservation Area near Brighton ON with a pine-grove course, post-race chili, touque and prize draws.
Weekend winter festival at Eganridge Resort with snowshoe and trail runs of 1 km, 5 km and 10 km, a torchlight 4k walk, family activities and championship awards.
Winter trail event in Elora and Fergus with 5 km, 10K and a 21.1 km half marathon on snow-covered trails, chip timing, finisher medal, and fundraising for Servant's Heart.
Classic technique cross country loppet on hilly trails in Brudenell Ontario with multiple distances, team and costume prizes, and online registration limited to 100 skiers.
February 2027
Snowshoe and trail race in Summerstown Forest with 8.5 km and 4.4 km options, limited entries, rental snowshoes and series points for the 8.5 km race.
A winter obstacle race at Albion Hills with a snowy 5-6 km course and 14 obstacles, finish-line hot chocolate and a metal finisher medal. Family discounts apply and a Polar Rush buff is included.
A 2027 cross country ski festival at Hardwood Ski and Bike with 15 km and 30 km skate and classic races, youth events, awards and s'mores over an open fire.
April 2027
Caledon Crusher is a trail ultramarathon in Mono ON with E2E about 76 km, 52 km and 27 km routes along the Caledon Hills Bruce Trail.