Trail Running calendar near Pickering 2026-2027

Join the Dion Mighty Chickadee Snowshoe Race at Cold Creek for a scenic 6.5 km through forest and meadow with a few climbs. Limited entries, snowshoe rentals and post run food plus awards make this a fun winter challenge.

Shake off winter with the Old Man Winter Trail Race at Marjim Manor, a scenic 3.2 miles through winery grounds and apple orchards on January 24, 2026. Register by Jan 16 for a special embroidered hat, chip timing, finish photos, and awards.

Take on scenic, hilly single loop trails at Pick Your Poison Trail Race in Copeland Forest with 12.5k, 25k or 50k options, three aid stations per loop and challenging elevation. This nonprofit event benefits local mental health programs and..

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.

Explore the Seaton Scramble Trail Race in Pickering on May 9, 2026 with scenic single and double track, creek crossings, stairs and viewpoints. Distances from a kids 1K to a challenging 50K suit every trail runner.

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..

Run Uxbridge offers scenic trail and road 10K, 5K and 1 km kids dash starting and finishing at Elgin Park in Uxbridge, Ontario. Enjoy a community race with age category awards and support for the Uxbridge Hospital Auxiliary.

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.

Run scenic Bruce Trail singletrack and Kelso Conservation Area on 10 km, 25 km or 50 km courses at the First Blaze Trail Race 2026. Fields capped at 200, with a finisher medal, shirt option, shuttle and a charity donation.

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

Tackle winding singletrack and hilly climbs along the Humber River at Albion Hills Conservation Park, part of the 5 Peaks Ontario Trail Running Series. Pick 7.5 km, 15 km or 22.75 km routes and enjoy camping, a park pool and finisher swag.

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.