Trail Running calendar near Courtland 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.

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 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.

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 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.

A 5 km run at Boler Mountain on July 25 2026 featuring over 25 obstacles, large foam zones using 2.5 million cubic feet of foam, plus a kids area, 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.

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.

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.

Tough Mudder Toronto on September 12, 2026 at Gopher Dunes offers 5K and 15K courses with multiple obstacles, finisher medals and a Mudder Village. Spectator passes, group packages and volunteer options are available.

Spartan Race comes to Gopher Dunes near London Ontario on September 13, 2026 offering a 5 km Sprint with 20 obstacles and a 10 km Super with 25 obstacles, plus PARA heats and spectator options.

A chip timed, two loop trail race covering 5 km at Bechtel Park in Waterloo. The event is part of the Run Pure + Simple series, free for Run Waterloo members and follows a strict non refundable registration policy.

A fundraising run at Kiwanis Park on September 19, 2026 offering timed 5 KM and 10 KM races plus a kids 200 m. Computerized timing, finisher medals, a technical t-shirt for the first 700 entrants, and post-race refreshments.

Trail races of 8 km, 16 km and 24 km run on an 8 km loop at Springwater Conservation Area in Aylmer on September 26, 2026. The night 8 km requires a headlamp and park admission is included with registration.