Trail Running calendar near Waterloo 2026-2027

Tails on Trails 2026 is a community fundraising run at Bechtel Park in Waterloo supporting the Humane Society of Kitchener Waterloo and Stratford Perth. Events include a chip timed 5 km, a 2.5 km fun run or walk and a 200 m pup run.

A 100 miles ultradistance route that circles the City of Hamilton starting in Carlisle. Finish the whole route within 40 hours for a gold buckle or spread the distance across June to earn a pewter buckle.

Multiple loop running options and duathlon formats start and finish at Vista Hills Public School on May 30, 2026. Courses run on open roads and results use Strava segment times and finish times.

A 5 Peaks Ontario race at Crawford Lake Conservation Area offering multiple distances, Indigenous Longhouses on site, cup free support, and on course aid stations with specific safety rules.

Community trail race in Streetsville along tree covered river paths. Offers a 1 km fun run for families and a chip timed 5 km; proceeds partly support Camp Wanago and an optional technical race shirt is available.

Hope in Motion 2026 in Caledon East offers cycling routes and 5 km and 10 km trails for walking, running, or rolling while raising funds for CMHA Peel Dufferin mental health and addictions services.

A timed 15:23 trail event at Marydale Park featuring an approximately 3.7 km loop, a relay option for teams up to five, one aid station per loop and race kit gels and a finisher medal. The event is listed as sold out.

Runners start together in London, Ontario and pick their own routes to get as far as possible from the start within set time limits. The race includes 8 hour, 4 hour and 2 hour categories and uses live tracking for verification.

Trail event on June 27, 2026 at Kelso Conservation offering 5K, 10K, MAX Elevation, 20K relay and kids options. The course uses roughly 3 km loops with notable elevation, aid stations and chip timing.

A 5K obstacle event at Victoria Park in Kitchener on July 11, 2026, featuring 25+ obstacles and 2.5 million cubic feet of foam. Festival features include a free kids zone, live DJ, food vendors and a licensed beer garden.

Trail races on the Toronto Bruce Trail near Milton, ON with 51.8 km and 27.5 km point-to-point options plus a hilly 10 km out-and-back. Technical singletrack on white-blazed routes, shuttle from Kelso, and a 200-person field limit.

A 5 kilometre obstacle run at Victoria Park in Kitchener on July 11 2026 with more than 25 obstacles and 2.5 million cubic feet of foam. The event includes a free kids fun zone, live DJ, food vendors and a licensed beer garden.

Six days and six stages covering 60 km in the Waterloo Cambridge area from July 13 to 18 2026 with a prologue on July 12. The event combines road trail cross country and track running and includes a technical T shirt and finisher medal.

Trail races at Area 8 Conservation Area on July 18 offering distances from kids 1 km to a 24.2 km Grit Run, with maps, aid stations and onsite awards for top finishers.

A 5K obstacle event at Boler Mountain on July 25, 2026 featuring 25 plus obstacles, 2.5 million cubic feet of foam, a free kids zone, live DJ, food vendors and a licensed beer garden.

Trail races at Dundas Valley Conservation Area offer a 7 km loop with rolling hills and about 130 m elevation per lap, multiple distance and timed formats, and an elimination Gong Show.

An affiliated backyard ultra on August 1, 2026 at Eco Park in Arva featuring hourly 6.7056 km loops, a 67 runner cap and a Silver Ticket for the winner providing World Team Championship entry.

Eight days and eight stages covering 80 km across road, trail, cross country and track in Waterloo Region from August 9 to 16, 2026, with kit pickup on August 8, on course fluids, a technical shirt and a finisher medal.

A mud and obstacle run at Albion Hills with a 6 km course, finisher medal, live DJ and food trucks. An all day pass lets participants run multiple times and the event is open to ages 12 and up.

Family fitness event at Gibbons Park offering adult, kids and dog obstacle courses across several distances. Obstacles are not revealed and specific rules apply for canine participants.