Trail Running calendar near Waterloo 2025-2026

Run the rugged Caledon Hills on the Caledon Crusher, a technical Bruce Trail race with sustained climbs and singletrack. Choose 25k, 50k or the epic 72k for scenic, challenging trail running.

Run scenic rail trail through Dundas Valley Conservation Area with 5, 10, 25, and 50 km options. Chip timing, finisher medals, and a charity fundraiser for Melanoma Canada make this spring race a community friendly challenge.

Rugged Raccoon Night Race at Wildwood on May 2 offers 10, 25 and 50 km trail runs under the stars. Expect rocky roots, climbs, lake views and muddy trails plus full aid stations and a finisher medal.

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.

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 at Bechtel Park to support the Humane Society of Kitchener Waterloo and Stratford Perth. Choose a 2.5 km loop, a 5 km challenge or a pup run and help raise funds for local pets.

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.

Celebrate the solstice at Marydale Park on June 20, 2026 with the Sunburn Solstice Trail Run, a time based 15:23 challenge on scenic 3.7 km loops through trees and fields. Solo runners or teams up to five earn a finisher medal and tee.

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.

Six days, six stages totalling 60 km through Waterloo region towns, from trails and cross country to track and road. Limited to 75 runners, ENDURrun Prelim blends competition and community with on course support, leader bibs, a finisher med..

Tally in the Valley returns to Dundas Valley in Hamilton on July 25 and 26, with scenic 7 km loops through Carolinian forest. Choose from 7 km, 21 km, 100 miles and 6 12 and 24 hour events, with La Sportiva demos and giveaways.

Take on ENDURrun 2026, an eight day staged adventure around Waterloo Ontario from Aug 9 to 16, with a 160 km Ultimate or an 80 km Sport across road, trail, cross country and track. Expect challenging stages and limited spots.

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 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..

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.

Run Sticks n' Stones at Christie Lake on runnable 5.3 km loops with distances from 5 km up to 53 km solo or relay. Proceeds support Oceana Canada, La Sportiva will host a demo and giveaway, and finishers receive a medal.

Run the Phoenix Trail Races at Fanshawe Conservation Area on scenic 25k or 50k looped trails with varied surfaces and fun technical sections. Timed results, aid stations, support and a finisher medal plus charity partner Animalert make for..

Tackle the Lost Valley Trail Race on the Iroquoia section of the Bruce Trail between Burlington and Dundas, with 10 km and scenic but rugged 25 km options. Limited to 180 runners, the course offers rocky single track, escarpment views and s..

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.