Trail Running calendar near Milton 2026-2027

A looped trail weekend in Ancaster offering 10K to 100 mile events on 20 km loops with over 500 m elevation per loop and four aid stations. The 100K and 100 mile races offer Western States qualifying opportunities.

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 Trail Running Series race at Crawford Lake Conservation Area with distances from 1 km kids races to an 18.4 km Grit run. The site features reconstructed Indigenous longhouses and on course aid stations; spectators are welc..

A 38th annual trail event in St. Catharines featuring a 21.1 km half marathon and a 7 km trail race with limited fields. The routes include the 12 Mile Creek Trail and Hydro Hill and support the Niagara Rankin Cancer Run.

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 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.

Commemorative run in Niagara-on-the-Lake honoring General Józef Haller and the Blue Army, with races from 1 km to 10 km along the Niagara Parkway Recreational Trail. Race kit items, finisher medal and a prize draw for a flight to Poland.

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.

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.

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 trail run at Bella Rose Vineyard in Lewiston, NY on July 19, 2026 offering a stemless wine glass and complimentary wine tasting for those 21 and older, professional timing, post-race snacks, and vineyard views.