Trail Running calendar near Pickering 2026-2027

An annual April trail race near Barrie Ontario offering 12.5 km 25 km and 50 km options on a 98% trail based course with notable climbs. Proceeds support local mental health organizations.

Join the 5 Peaks Trail Running Series at Kelso in Milton for forest trails with steep climbs and flowing descents. Pick distances from kids races to 20.6 km and enjoy scenic singletrack, aid stations and a lively finish.

Trail race on the Seaton Trail near Pickering with distances from a 1K kids run to a 50K double loop. The out and back course is well marked and includes single and double track, a creek crossing, stairs and a nine hour cutoff.

Join Hope in Motion 2026 on June 7 in Caledon East for a community fundraiser supporting CMHA Peel Dufferin with cycling, walking, running and rolling for all abilities. Choose distances from 5 km trails to 100 km rides and help raise funds..

Trail event on June 13, 2026 at Earl Rowe Provincial Park in Alliston offering looped distances from 6K up to 62K plus a 12K virtual option. Mostly wide trail with varied surfaces, aid stations, cup free service and a finisher medal.

A community fundraising run in Uxbridge with 10 km and 5 km run and walk options plus a 1 km kids dash. Net proceeds support equipment and furnishings for the new Uxbridge Hospital.

Tackle technical singletrack and big climbs in Durham Forest at The Whole Enchilada on June 20, 2026, with distances from a 1 km kids dash to a challenging 50 km. Eco friendly cup free event at Trail Hub with aid stations and onsite awards.

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.

Trail races along the Toronto Bruce Trail on July 11, 2026, offering approx. 52 km, 27.5 km and 10 km options, point to point courses with shuttle service for longer distances and cup free aid stations.

The 5 Peaks - Area 8 will take place in Milton on Saturday 18 July 2026. You can run between 8 and 24 kilometers.

Trail races at Albion Hills Conservation Park on September 5 feature singletrack routes along the Humber River, camping options and a pool. Distances include 7.5 km, 15 km and 22.75 km.

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.

Run the Heart Lake stop of the 5 Peaks Ontario Trail Running Series on Saturday October 3, enjoying shaded trails, fall colours and lake views. Choose distances from a kids run to longer challenge and soak up a friendly trail race vibe.

Explore two scenic 7 km trail loops at Long Sault Conservation Area in Bowmanville this October with distances from 7K to 21K plus a 6 hour endurance challenge and a 2K kids run. Trail snacks, on course support, and community vibes await.

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.