Trail Running calendar near Oakville 2025-2026
We have found 24 Trailruns within 80 kilometers of Oakville. See below where and when you can find the races.
Distance (km)
Articles
Belgian Ultrarunner Karel Sabbe's Record-Breaking Pacific Crest Trail Run Showcased in New YouTube Documentary
Explore Karel Sabbe's record-breaking Pacific Crest Trail run in a riveting documentary. Jour..
Trail Running: How it Can Help Reduce Stress and Anxiety
Trail running is an effective way to reduce stress, anxiety, and improve physical and mental he..
Trail Running vs. Road Running: Which One Is Right For You?
When it comes to running, there are two primary options to choose from: trail running and road..
Caledon Crusher 2026 is a trail-running event in Ontario’s Caledon Hills, centered at Mono Centre Park in Shelburne. It offers 25k, 50k and End-to-End 72k routes along the Caledon Bruce Trail. Runners traverse rugged singletrack and sustained climbs with elevations of about 850m (25k), 1,200m (50k),..
May 2026
Tails on Trails 2026 is a community fundraising race in Bechtel Park, Waterloo, Ontario, in support of the Humane Society of Kitchener-Waterloo and Stratford Perth. Returning for a second year, the event offers dog-friendly and human-only options: a timed 5K Trail Race with a canine + handler, a tim..
July 2026
The ENDURrun Prelim is a six-day endurance challenge totaling 60 km in Ontario, Canada. The event begins with a prologue at Weberlyn Crescent, Conestogo, and features stages across Waterloo, Cambridge, and Wilmot (RIM Park, Riverbluffs Park, Bechtel Park, Baden Hills, and a Waterloo track venue). St..
August 2026
The ENDURrun is a week-long endurance challenge held in Ontario, Canada, organized by Run Waterloo. It offers two formats: The ENDURrun 160 KM Ultimate (8 days, 7 stages) and The ENDURrun Sport 80 KM (8 days, 8 stages). Runners traverse varied terrain around Waterloo Region, with venues at RIM Park..