Trail Running Calendar Ontario 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..

This trail run near Barrie features a challenging 12.5 km loop, with 12.5 km, 25 km, and 50 km distance options. Finishers earn unique technical socks and local honey. The event is operated sustainably as a cupless race, with proceeds suppo..

Southern Footprints features 5K, 10K, and 15K runs through Point Pelee National Park. The looped course mixes road and trail running. The event also includes a walk, a kids' dash, and a mascot race.

A trail running adventure by day and night on the scenic paths around Wildwood Lake. Choose from 10km, 25km, or 50km distances, with night runs requiring a headlamp. Supports Ontario Nature and includes a medal, shirt, and aid stations.

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.

An annual trail race on the Sawmill Ski Trails in Hepworth, supporting a local youth ski team. Choose from distances ranging from 2.5 km to a 6-hour endurance event. It's a capped event with chip timing and part of the OUTRace Trail Series.

Explore quiet country roads at the historic Ecotay farm during this spring run. Choose between a 6K or 10K loop. After the race, enjoy a breakfast sandwich, a medal, and live entertainment.

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..

Trail run of 8 km at Goodrich-Loomis Conservation Area as part of the Happy Hour Friday Night Series. The course includes hills, rocks, roots and mossy log bridges; the event is cupless with water at the start and finish.

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.

A trail half marathon of 21.1 km and a 7 km trail race through historic parts of St. Catharines including the 12 Mile Creek Trail. Limited fields and a walker division that uses the same route.

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..

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..

The Boomerang Trail Run is a 7 km looped trail race in the hills of Batawa, Ontario. Choose your challenge by running as many laps as you can in 2, 4, or 6 hours. The event has a relaxed vibe, with a cup-less aid station and manual lap timi..