Trail Running calendar near Milton 2026-2027

Trail event at Earl Rowe Provincial Park offering loop distances from 6K to 62K, cup-free aid stations, drop bags and finisher swag; proceeds support Procyon Wildlife.

A commemorative run in Niagara-on-the-Lake honoring General Józef Haller and the Blue Army, with a 1 km kids race, 5 km family and run/walk events, and a 10 km open race. The out and back course follows the Niagara Parkway Recreational Trai..

A checkpoint format trail race of 10 to 15 km in Toronto on June 13, part of a series across Canada. Runners choose checkpoint order and pace, with an after race morning party featuring coffee, food, DJs and prizes.

A 15 hours 23 minutes trail event on June 20, 2026 at Marydale Park offering an individual timed option and a relay for teams up to five. The course uses an approx 3.7 km loop on mixed trails with one aid station per loop.

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.

A point to point trail race on the Toronto section of the Bruce Trail on July 11, 2026, offering 50 km, 27.5 km and 10 km courses. Routes follow white blazes through conservation areas and notable sites with spaced aid stations and technica..

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 totaling 60 km around Waterloo and Cambridge in July 2026. A multi-discipline event combining road, trail, cross country and track with a tech shirt and finisher medal.

A trail running event at Area 8 Conservation Area on July 18 with distances from a 1 km kids race to a 24.2 km Grit Run. The former limestone quarry now features trails along the escarpment.

A weekend trail event at Dundas Valley Conservation Area on July 25 2026 featuring a 7 km loop plus multi loop and timed options, including a Gong Show elimination format. Finishers of 100 miles receive a custom belt buckle.

Eight consecutive stages across the Waterloo region totaling 80 km, combining road, trail, cross country, time trial and track races. Includes a technical t shirt, finisher medal, on course fluids and limited post race refreshments.

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.

Raid the City is a three hour urban navigation race in Hamilton where teams of two collect points at checkpoints across trails, roads, alleys and parks. Teams must run on foot and use a smartphone app to track checkpoint visits.

Part of the 5 Peaks Trail Running Series, this event at Albion Hills Conservation Area in Caledon on September 5, 2026 features multiple course options including kids races and variable entry fees.

Trail races at Albion Hills Conservation Park feature singletrack trails along the Humber River. Distances range from 7.5 km to 22.75 km, with camping, family facilities, a pool, and cup free water stations.

UNFINISHED is a Backyard Ultra at Woodbine Beach Park on September 12, 2026 featuring repeated 6.71 km loops. Options include Backyard Ultra solo or teams of three, a 15 hour Endurance window, and a community Sunshine Yard.

A family adventure event in Mississauga on September 12, 2026 with courses for adults, children and dogs. Survival style challenges take place across varied terrain, obstacles are not revealed and tickets range from 40.54 CAD to 107.64 CAD.

Beat Bechtel is a certified two loop trail 5 km at Bechtel Park in Waterloo on September 13 2026. The chip timed event has minimal extras, is free to Run Waterloo members, and lists a base fee of $15 plus fees.

A community run through the vines at Palatine Hills Estate Winery featuring a timed 5 km race, untimed family and dog walks, post-run food and music, and winery perks. A portion of proceeds supports Community Care.