Trail Running calendar near Milton 2025-2026

Run the 5 Peaks Trail Running Series at Area 8 Conservation Area in Milton on September 5, 2026. Enjoy rolling singletrack, friendly competition and scenic views as part of the Ontario West series.

Join the 13th Kitchener Kids with Cancer on Sept 19 at Kiwanis Park for scenic trail 5 km and 10 km races that benefit pediatric cancer care. Family friendly with a free kids 200 m, medals for finishers, music and food trucks after the race..

Join the 5 Peaks Trail Running Series at Heart Lake Conservation Area in Brampton on October 3, 2026 for a scenic trail running challenge suitable for all levels. Enjoy varied terrain, great views, and the chance to support local charities.

Join Sticks n' Stones at Christie Lake for rolling dirt loops around the lake with distances from 5k to a 53k solo or team relay. Enjoy La Sportiva demos, aid stations and medals while supporting Oceana Canada.

Choose 10 km or 25 km on the Bruce Trail for scenic single track and rocky views along the Niagara Escarpment. Enjoy aid stations, shoe demos and a lively finish at Dundas Valley Conservation Area.

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.