Trail Running calendar near Pickering 2025-2026

Hit the trails at Cold Creek on Jan 11, 2026 for the Dion Mighty Chickadee Snowshoe Race, a scenic 6.5 km through forest and meadows. Limited spots and snowshoe rentals make this a cozy, competitive winter outing.

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.

Tackle single track trails and ski hill climbs at Pick Your Poison Trail Run in Copeland Forest near Barrie Ontario. Choose 12.5k, 25k or 50k loops, enjoy three aid stations per loop and help support local charities.

Join the 5 Peaks Trail Running Series at Kelso Conservation Area on May 2, 2026 for trail runs from a fun 1 km kids race to a challenging 21 km grit course. Scenic singletrack and options for all abilities make it a great spring outing.

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.

Run the 5 Peaks trail race at scenic Crawford Lake with distances from 1 km kids races to an 18 km challenge. Enjoy forest trails, reconstructed Indigenous longhouses and a welcoming community of spectators and volunteers.

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.

The Whole Enchilada in Uxbridge invites trail lovers to tackle scenic, technical routes through Durham Forest with steep climbs and thrilling descents. Distances from 1 km fun runs to a challenging 50 km mean something for every runner, wit..

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 winding singletrack along the Humber River at Albion Hills Conservation Park, with options for beginners to experienced trail runners and family friendly kids races. Enjoy on site camping and a pool for a fun post race unwind.

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.

Hit the trails at Long Sault Trail Race & Ultra in Bowmanville on October 17, with looped 7K courses from a kids fun run to a timed six hour ultrarun. Expect scenic single track, a friendly aid station, and community vibes with hoodies supp..

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.