Trail Running calendar near Brampton 2025-2026

Chill Session 2025 is a trail-running event held at Mansfield Outdoor Centre in Mulmur. Runners can choose from 10K Chill, 5K Cool, or 1K Wee Chilly for kids. The courses are mostly single-track with elevation gains around 220m for the 10K and 130m for the 5K, and are marked with hot-pink arrows and..

The Leftovers Mystery Race 2025 takes place at Dundas Valley Conservation Area on Governors Road in Dundas, Ontario. This playful trail event features mystery distances you choose on race day: a short option 6 km or less, a medium 10–15 km, and a longer 16–25 km. The course is a well-marked, scenic..

The Golden Spike Trail Race is a winter trail running event at Crawford Lake Conservation Area in Milton, Ontario. Participants choose from 5K, 10K, or 21K, dashing through snowy forest, a boardwalk around the lake, and rugged Bruce Trail sections by a canyon. The course blends fast main-trail segme..

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),..

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 Whole Enchilada is a trail running race held at Trail Hub in Uxbridge, Ontario, in Canada’s trail capital, Durham Region. It offers multiple distances: The Full Enchilada (50 km), Half Enchilada (25 km), Mini Enchilada (8 km), Hike Enchilada (4 km), plus Kids Enchilada (4 km) and Kids Salsa (1 k..

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..

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..