Trail Running calendar near Milton 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..

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.

The Great Mansfield Outdoors is a trail run on the single-track paths of Mansfield Outdoor Centre and Dufferin County Forest. A new 100 km solo and relay distance debuts in 2026. This cup-free event offers races from 5 km to 100 km, with on..

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.

The 38th annual trail half marathon and 7k takes place in St. Catharines. The historic half marathon course follows the first Welland Canal and descends the Niagara Escarpment. Participation is capped and the event supports the Niagara Rank..

Hope in Motion is the Canadian Mental Health Association Peel Dufferin's major annual fundraiser. Choose from cycling routes of 25 to 100 km or walking/running trails of 5 and 10 km at the Caledon East Community Complex. Participate on-site..

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..

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..

The fourth 5 Peaks event in Ontario is at Area 8 Conservation Area, with routes from 1 km kids races to a 24.2 km Grit Run, mapped aid stations, parking, washrooms, and a cup-free policy.

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..

The ENDURrun is the ultimate test of endurance: 160 km across seven stages over eight days in August 2026. The challenge includes a half marathon, cross country, marathon, and time trials. Relay team and individual stage guest options are a..

The 5 Peaks Albion Hills trail run takes place in the scenic Albion Hills Conservation Park. With distances from 7.5 km to 22.75 km, it offers singletrack trails and family-friendly activities like camping and a pool.