Trail Running calendar near Pickering 2026-2027

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..

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..

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.

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 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.

Enjoy the autumn scenery at Heart Lake Conservation Park with trail races ranging from 1 km to 22.5 km in a beautiful forested setting.

This community trail race offers distances for everyone at the Long Sault Conservation Area. Choose from a 2K kids run, 7K, 14K, 21K, or a six-hour ultra on scenic trail loops. Parking is limited and supports the conservation organization C..

The Beav Trail Race at Hilton Falls on October 31 offers 10 km, 25 km and 50 km on fast but technical trails with scenic waterfall views. Bring your own cup or bottle as no cups are provided, and finishers earn a custom medal and apparel.