Trail Running calendar near Pickering 2025-2026

Hit snowy trails at the Golden Spike Trail Race around scenic Crawford Lake in Milton, Ontario on December 6, 2025. Choose 5K, 10K, or 21K and support STAC Hamilton youth programs while enjoying winter forest views and warm aid stations.

Join the Dion Mighty Chickadee Snowshoe Race on January 17 at Cold Creek Conservation Area for a scenic 6.5 km through forest and meadows with a few long climbs. Limited to 60 racers, this series stop wraps up with chili, awards and prize d..

Old Man Winter Trail Race at Marjim Manor in Appleton NY on Jan 24, 2026 invites runners to a scenic 3.2 mile loop through orchard and farm trails. Register early for an embroidered hat and enjoy chip timing and on site race gifts.

Take on Pick Your Poison, an annual April trail ultra around Horseshoe Heights near Barrie. Choose 12.5k, 25k or 50k loops, enjoy aid stations and boxed meals, and support mental health awareness.

Join the 5 Peaks Trail Running Series at Kelso Conservation Area in Milton Ontario on May 2, 2026. Distances from a 1 km kids run to a 21 km grit course mean every runner can enjoy scenic trails and friendly race vibes.

Race the Seaton Scramble on May 9, 2026 in Pickering along scenic single and double track trails with creek crossings, stairs, hills and viewpoints. Distances from a 1K kids run to a double loop 50K support Lakeridge Health Foundation.

Explore rolling singletrack and technical forest trails at The Whole Enchilada in Uxbridge, Ontario, with distances from a 1 km kids fun run to a challenging 50 km. Enjoy scenic routes, on site aid stations, and a community minded vibe.

Run the Bruce Trail at Kelso Conservation Area on July 11, 2026 with 10, 25 and 50 km point to point courses for a capped field of 200. Expect varied single track, aid stations and shuttles, plus a donation to the Toronto Bruce Trail Club.

Run scenic 7K trail loops at Long Sault Conservation Area with options from a kids 2K fun run to a 6 hour loop challenge. Proceeds from hoodie sales support CLOCA and sponsors include Running Room and MEC.

Run scenic, mostly fast trails at Hilton Falls with 10 km, 25 km and 50 km distances to suit every trail runner. Enjoy a few technical sections, a waterfall pin, on course s'mores, La Sportiva shoe demos and finisher swag.