Trail Running calendar near Alliston 2026-2027

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 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..

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..

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 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.

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..

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.

The Summit 700 Trail Runs challenge runners on Blue Mountain Resort's single-track trails in Ontario. Choose from distances including 5K, 10K, 21K, and a 50K Ultra, all featuring a signature 700-foot timed climb. The event finishes with a f..

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 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.

The Distances Participants can choose between two distances. Trail Marathon (42.2 km) Trail Half Marathon (21 km) There is also a combined option called The Bruce Deuce, which involves running the full marathon on Saturday and the half ma..

The Devil's Key features three demanding trail races on Ontario's Bruce Trail near Duntroon. Runners tackle significant climbs, must crawl through a unique "keyhole," and are tasked with keeping a skeleton key throughout the race. Part of e..

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.

Trail event at Slabtown Cider Co. on private Woodnewton Farm trails near Uxbridge. Multiple distances from a kids 1K fun run to a 40K five loop race and fundraising for local trail restoration.

A three-day stage race at Blue Mountain Resort, featuring a different format each day: vertical climb, distance grind, and a timed loop finale. Enjoy daily awards, social events with meals and music, and full safety support. Ontario's only..