Trail Running calendar near Caledon 2026-2027

A flat and fast 5km race along Hamilton's waterfront trail and through Bayfront Park. Runners get a technical shirt, a finisher's medal, and post-race hot food. Awards are presented for overall and age-group winners.

The Caledon Crusher is a trail run on the technical paths of the Caledon Hills along the Bruce Trail. It offers three distances, from 25 km to 72 km, with significant elevation gain. All races finish at Mono Community Centre, where a post-r..

This flat and fast rail-trail race offers four distances starting from the Dundas Valley Conservation Area. It's an event held in memory of Paul Turkstra, supporting melanoma awareness. Runners receive a t-shirt and medal on a well-supporte..

Choose your distance from 12.5 km to 50 km in this eco-friendly trail race featuring stunning vistas, forest single-track trails, and challenging ski hill climbs in Ontario.

The 5 Peaks series kicks off in Milton at the Kelso Conservation Area. This trail running event offers multiple distances, including a 21 km course. It's the first stop on the Ontario series.

The Seaton Scramble Trail Race features an out-and-back course on the Seaton Trail, with creek crossings, hills, and stairs. Distance options range from a 1 km kids run to a 50 km ultramarathon, open to runners and hikers. A 9-hour time lim..

A historic looped trail race in the Dundas Valley, offering distances from 10k to 100 miles. Features a hilly 20k loop, is a cup free event, and a Western States qualifier. Canada's oldest ultra trail race.

Tails on Trails returns for a second year at Bechtel Park. This fundraising event features 5k and 2.5k courses to run or walk, with or without a canine companion. A short 200m pup run is also offered for four-legged participants.

Test your limits on the single track trails of Dufferin County Forest with distances ranging from 5 km to a 100 km ultramarathon available for solo runners and relay teams.

The Trail Terrier Ultra Around Hamilton is a 100-mile event that circumnavigates the city. Runners can choose to tackle the distance in one 40-hour push or spread it over the month of June. Everyone who finishes earns a commemorative belt b..

The 5 Peaks Trail Running Series comes to Crawford Lake in June 2026. This trail run takes place at the Crawford Lake Conservation Area in Milton. Swag is optional and park fees may apply.

Join Hope in Motion 2026 in Caledon East for a day of cycling, running, and walking to support mental health services. Choose from distances up to 100 km and help make a direct impact in the Peel Dufferin community.

The Distances The event offers three trail running distances on the Bruce Trail: 200 Miler (322 km): An out-and-back course starting in the Blue Mountains, running through the Dufferin Hi-Land section, and turning around at Glen Haffy in t..

Join the 5th annual Rainbow Trail Run in the scenic Earl Rowe Provincial Park. This trail running event offers distances from 6 km to 62 km on a relatively flat, looped course through the park. It's a cup-free event with a post-race BBQ and..

The 19th Uxbridge Run for the Diamond offers 5K and 10K trail run/walk events and a Kids Dash. Proceeds benefit the local hospital, and adult participants are entered into a special diamond draw.

The Whole Enchilada is a trail running event set in Durham Region, Canada's trail capital. It features distances from a 1 km fun run to a demanding 50 km route. The race focuses on sustainability, being cup-free and supporting local environ..

Trail running event at Kelso Conservation on June 27, 2026 offering 2K, 5K, 10K, MAX Elevation and a 20K relay. Courses include aid stations, professional chip timing and a post event village with awards.

A point-to-point trail adventure on Ontario's iconic Bruce Trail. Choose from three distances, exploring unique conservation areas and historic trail sections. This grassroots event supports trail maintenance and offers a true back-to-natur..

The ENDURrun Prelim is a six-day, six-stage challenge totalling 60 km. It blends road, trail, cross-country, and track racing on varied courses across Ontario. A complete test of endurance with a finisher's medal and technical shirt for all..

Run a 7 km loop through the Carolinian forest of Dundas Valley. Choose from distances ranging from a single loop to a 100-mile ultra or the unique "Gong Show" elimination race. All finishers get a medal, and early registrants receive a race..