Trail Running calendar near Caledon 2025-2026

Take on ENDURrun Prelim, a six day, six stage 60 km challenge across Waterloo and Cambridge, featuring trails, track heats and a final half marathon. Spots limited to 75; entries include a technical T shirt and finisher medal, with aid stat..

Hit the trails at Albion Hills on July 18, 2026 with the 5 Peaks Trail Running Series. Scenic, challenging and fun, this 5 Peaks Ontario Series stop welcomes runners looking for a memorable outdoor race.

Tally in the Valley returns July 25 and 26 2026 at Dundas Valley near Hamilton with scenic 7 km forest loops and rolling hills. Distances run from 7 km to 100 mile with 6, 12 and 24 hour timed options and finishers get buckle or medals.

Run the Falling Water Trail Marathon or Half in Eugenia on Aug 8 and 9, 2026 on the rugged Bruce Trail. Limited to 100, this hilly single track race offers a two day option for two medals and benefits the trail club.

Experience ENDURrun 2026, an eight day seven stage 160 km running adventure in Conestogo, Ontario from August 9 to 16. Road, trail, cross country and track stages include a marathon and half marathon with daily time limits and on course aid..

Timber24 is a 24 hour trail relay at Hardwood Ski and Bike near Barrie where teams of 4 or 8 cover 192 km by sending a runner on an 8 km lap every hour. Expect a festival atmosphere with on site camping, food, an expo and a Beer Garden.

Tackle rugged Bruce Trail terrain at Devil's Glen on scenic courses from 16 to 66 km, featuring steep climbs, a keyhole crawl and riverside sections. Entries support the Blue Mountains Bruce Trail Club and include a race kit and finisher me..

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.

Test your climbing legs at the Creemore Vertical Challenge in October, with distances from 14K to 80K over scenic gravel roads and trails. Expect big climbs, helpful aid stations, and a festive small town finish.

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.