Trail Running calendar near Caledon 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.

Trail races from 5 km to a new 100 km solo or relay at Mansfield Outdoor Centre, with cupless aid stations, on-site camping and race services.

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 multi-distance trail event on the Bruce Trail offering 200 miles, a point to point 100 miles and a 72.5 km E2E, with white-blaze navigation, many aid stations and substantial elevation gain.

A six date summer series of flagged trail runs, hikes and walks in The Blue Mountains with season and single event options, social meetups, Strava challenges and fundraising for local trail organizations.

A trail race at Earl Rowe Provincial Park on June 13 2026 offering distances from 6K to 62K plus a Canadian virtual option. Mostly flat 12K loop, aid stations, cup free policy and a custom finisher medal.

A checkpoint-style trail race in Toronto on June 13, 2026, organized by Slowpokes with The North Face, featuring an approximately 10-15 km route, checkpoint navigation, and a morning post-race party with coffee, food, DJs and prizes.

Two trail-and-road runs in Uxbridge : 10 km and 5 km : starting and finishing at Elgin Park. A fundraiser for the new Uxbridge Hospital, with online registration open Feb 1 to June 10, 2026.

Trail running at Trail Hub in Uxbridge on 20 June 2026, with distances from a 1 km kids fun run to a 50 km end-to-end route, marked trails, aid stations and sustainability measures.

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.

Utopia Backyard Ultra at the Tiffin Centre on June 27-28 2026 is a loop every hour event that continues until one finisher remains. Several fixed duration options are offered and start area camping is included for entries.

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.