Trail Running calendar near Oakville 2025-2026

The Tally in the Valley Trail Race takes place in the scenic Dundas Valley Conservation Area in Hamilton, Ontario, Canada. This event features a 7km loop through a unique Carolinian forest with rolling hills and about 130m elevation gain per loop. Participants can choose from various distances and f..

The Wolfpack Ultra Championship is a premier trail running event held in Hamilton, Ontario, Canada, on September 20, 2025. Featuring a challenging 50K ultra-distance race through the scenic and technical trails of Conservation Halton, the event tests endurance with rugged terrain, technical climbs,..

The Willibald Pasture Dash is a cross-country style running event held at Willibald Farm Distillery & Brewery in Ayr, Ontario, Canada. Participants race on a scenic 2.5km looped pasture course, choosing between 5km (two loops) or 10km (four loops) distances. The event offers a rustic, country atmosp..

The Albion Ascent Trail Race in Hamilton, Ontario, offers a scenic and challenging urban trail running experience through rivers, waterfalls, and forests. Featuring 5K, 10K, and 21K distances, the race showcases the natural beauty of King’s Forest, the Bruce Trail, and landmarks like Felker’s Falls..

The Pace for the Donkeys 5k Trail Run is a scenic running event held at the Donkey Sanctuary of Canada in Puslinch, Ontario. Participants can choose between a 5K trail run or a leisurely 1K stroll through beautiful fields and trails. The event welcomes runners and walkers of all levels, offering a f..

The Sticks N' Stones Trail Race is held at Christie Lake Conservation Area in Hamilton, Ontario, Canada. This event features multiple distances including 5k, 10k, 25k, and 50k races, with a 50k relay option for teams of up to five. The course consists of a scenic, rolling 5.3 km loop around the lake..

The Wise Raven Trail Race is an annual trail running event held at Camp Heidelberg, Kressler Road, Waterloo, Ontario, Canada. Celebrating its 10th year, the race supports the WRHNCC charity and is sanctioned by Athletics Ontario. The course features a 2.5 km loop through well-marked forest trails wi..

The Beav Trail Race is an annual trail running event held at Hilton Falls Conservation Area in Milton, Ontario, Canada. The race features three distances: 10km, 25km, and 50km, with the 50km being two loops of the 25km course. The course is known for its fast, groomed trails combined with technical..

The Oakville Remembrance Trail Run is an 11km trail running event held in Oakville, Ontario, Canada, specifically on the trails of Lions Valley. This inaugural run honors veterans, first responders, and their families, serving as a remembrance movement rather than just a race. Participants experienc..

The Lost Valley Trail Race is a trail running event held at Dundas Valley Conservation Area in Dundas, Ontario, Canada. Scheduled for November 15, 2025, it offers two point-to-point race distances: 10 km and 25 km, both following the scenic Iroquoia Section of the Bruce Trail. The courses feature a..

The Chill Session 2025, hosted by North of 89 Outdoors, is a trail running event held at the Mansfield Outdoor Centre in Mulmur. It features three race distances: a 10K with about 220m elevation gain, a 5K with 130m elevation gain, and a 1K kids' race for ages 10 and under. The courses are mostly si..

The Leftovers Mystery Race is a unique running event held at Dundas Valley Conservation Area in Dundas, Ontario, Canada. Scheduled for December 6, 2025, this race offers participants a choice of three mystery distances: short (6k or less), medium (10-15 km), and long (16-25 km), with the exact route..

The Golden Spike Trail Race is a winter trail running event held at Crawford Lake Conservation Area in Milton, Ontario, Canada. Scheduled for December 6, 2025, it offers three distances: 5K, 10K, and 21K, catering to all levels from beginners to seasoned trail runners. The course features scenic, sn..

Tails on Trails 2026 is a community fundraising running event held at Bechtel Park in Waterloo, Ontario, supporting the Humane Society of Kitchener-Waterloo and Stratford Perth. Participants can join a 5K or 2.5K trail race or walk, with options to run with or without a canine companion. There is al..

The ENDURrun is a challenging multi-stage running event held in Conestogo, Ontario, Canada. The 21st edition in 2026 spans 8 days and 7 stages, covering a total of 160 kilometers. The race features diverse courses including half marathons, time trials, cross country runs, hill runs, technical trail..