Trail Running calendar near Brampton 2025-2026

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.

Run the DSpring Fling 5 km along Hamilton's scenic waterfront and Bayfront Park on a flat, traffic free, fan friendly course. Enjoy chip timing, a custom finisher medal and post race food and photos.

Tackle the rugged Caledon Crusher on the Bruce Trail with 25k, 50k or epic 72k options featuring technical singletrack and big climbs as you finish at Mono Centre Park in Shelburne. Support the Bruce Trail and refuel at well stocked aid sta..

Challenge yourself on the Foxtail Rail Trail Race in Dundas Valley, offering 5, 10, 25 and 50 km options on a fast, wide rail trail with start and finish at the Trail Centre. Enjoy aid stations, chip timing, race photos and finisher medals..

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 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.

Sulphur Springs Trail Race in Dundas Valley, Hamilton on May 23 and 24 offers looped 20K terrain with distances from 10K to 100 miles plus team relays. Rugged trails, big climbs, and crew access make for a classic spring ultra.

Join Tails on Trails on May 30, 2026 at Bechtel Park in Waterloo to support Humane Society of Kitchener Waterloo and Stratford Perth. Choose 2.5 km or 5 km loops, bring your pup or run solo, and help raise funds in a fun family atmosphere.

Experience rugged single track trails at Great Mansfield Outdoors on May 30 2026 with looped 25 km courses for distances from 5 km to epic 100 km. Scenic forest terrain, full aid stations and camping make it a perfect trail running getaway.

The 5 Peaks - Crawford Lake will take place in Milton on Saturday 6 June 2026. You can run between 6 and 18 kilometers.

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.

Join the Sunburn Solstice Trail Run at Marydale Park for a scenic, time based trail challenge with solo and team relay options on tree covered loops. Enjoy community vibes, gear demos and help send kids with disabilities to camp.

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.

ENDURrun Prelim is a six stage 60 km running challenge across southern Ontario from July 13 to 18 2026. Enjoy road, trail, cross country and track stages around Waterloo and Cambridge for a varied and fast paced multi terrain adventure.

Tally in the Valley Trail Race brings runners to Dundas Valley for scenic 7 km loops through Carolinian forest and rolling hills. Distances range from 7 km to a 100 mile challenge with a custom buckle for 100 milers while supporting SickKid..

Race 80 KM over eight varied stages across road, trail, cross country and track near Conestogo Ontario, August 9 through 16 2026. Limited to 75 participants with kit pickup and finisher medals for all finishers.

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.

Join the 13th annual Kitchener Kids with Cancer on Sept 19 at Kiwanis Park to support the Pediatric Oncology Group of Ontario. Choose a timed 5 KM or 10 KM on scenic park trails, earn a finisher medal and enjoy family friendly fun.