Trail Running calendar near Milton 2025-2026

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..

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..

ENDURrun is a week-long endurance challenge in southern Ontario, Canada, organized by Run Waterloo. The flagship ENDURrun 160 KM spans eight days and seven stages, totaling 160 km, with routes across the Waterloo Region—from RIM Park in Waterloo (opening stage) through Shade’s Mills in Cambridge, Ba..