Trail Running calendar near Oakville 2026-2027

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.

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.

Mud Hero Toronto is a 6 km mud obstacle event at Albion Hills on August 22, 2026. The program includes mud obstacles, a finisher medal, live DJ, food trucks, and paid onsite bag check and parking.

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.

A 5 Peaks trail running event at Albion Hills on September 5, 2026 offering multiple adult and kids course options, tiered registration fees and course maps and schedules published online. Fundraising partners are listed.

Trail races at Albion Hills Conservation Park in Caledon feature singletrack courses with winding climbs and multiple distance options. Camping, pool access and post-run activities are available at the park.

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.

An in person family-oriented survival challenge at Paramount Fine Foods Centre in Mississauga, with categories for adults, kids and K9 owners. The organizer describes varied terrain and unrevealed obstacles in a roughly two hour format.

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 family-friendly vineyard event at Palatine Hills Estate Winery offering a timed 5 km race plus untimed 1.25 km family and dog walks, with on-site vendors, prizes, and water stations.

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.

Albion Ascent is a transit friendly chip timed urban trail race in Hamilton offering 21k, 10k, 5k and kids runs. Routes go through King's Forest, the Bruce Trail and past waterfalls, toque included and medals optional.

A charity trail run at The Donkey Sanctuary of Canada in Puslinch on September 27, 2026, offering 5K and 1K routes. Entry fees support the sanctuary and fundraising aims for CA$30,000.00.

A pasture cross country race at Willibald Farm in Ayr on September 27 2026, run on a 2.5 km loop with 5 km and 10 km options. Race proceeds will support the rare Charitable Research Reserve.

Part of the 5 Peaks Ontario series at Heart Lake Conservation Park, featuring shaded trail routes and distances from 3 km to 22.5 km. The event is cup-free with aid stations, limited parking, and on-site washrooms.

Looped 5.3 km course at Christie Lake on October 10, 2026, offering 5.3 km, 10.6 km, 26.5 km and 53 km solo or relay options. Cupless aid stations provide drinks, snacks and gels from a local nutrition partner.

Looped trail race at Camp Heidelberg on October 17, 2026 offering distances from 5 km to 50 km plus a 6 hour option and relay. The event is sanctioned, electronically timed, and donates excess funds to Run Walk Roll for WRHNCC.

Point to point trail races finishing at Dundas Valley Conservation Area with 10 km and 25 km options, included transport from finish to start and on-course aid stations.

Trail races at Hilton Falls on November 7, 2026 with 10 km, 25 km and 50 km options. Routes mix groomed and technical trails, include aid stations and cup free service.

A trail running event in Oakville on November 7, 2026, offering 5 km and 11 km routes through Lions Valley, held in honour of veterans and first responders with proceeds to Wounded Warriors Canada.