Trail Running calendar near Milton 2026-2027

A 5 Peaks Trail Running event at Area 8 Conservation Area on a former limestone quarry, offering routes from 1 km to 24.2 km with mapped courses, aid stations and medals for top finishers.

Trail event at Dundas Valley Conservation Area featuring a 7 km loop, multi-loop and timed formats including a 100 mile challenge and an elimination Gong Show.

Eight days and eight stages across Waterloo Region from August 9 to 16, 2026, combining road, trail, cross country and track. Technical shirt included and finisher medal awarded; entries are limited and non refundable.

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.

Trail running and hiking event at Albion Hills Conservation Area in Caledon on September 5, 2026 offering multiple adult and kids courses with fees in Canadian dollars and fundraising pages.

Trail running at Albion Hills Conservation Park on singletrack with three distances, family facilities, camping and pool. Swag and finisher medals available for purchase and the event is cup free.

A chip timed trail race at Bechtel Park in Waterloo on September 13, 2026. The certified 5 km runs as two loops with limited services and free entry for Run Waterloo members.

A community fundraising run at Kiwanis Park in Kitchener on September 19, 2026 offering 5 km, 10 km and a kids 200 m. The event benefits the Pediatric Oncology Group of Ontario and includes a technical t-shirt for early registrants and fini..

A transit-friendly, chip-timed urban trail race in Hamilton offering multiple distances through King's Forest, the Bruce Trail and scenic waterfalls. Aid stations are cupless and a Canadian made toque is included.

A 5 km trail run with a 1 km option at the Donkey Sanctuary of Canada in Puslinch on 27 September 2026, supporting sanctuary fundraising. Listed fee CA$40 and teams registered by 31 July enter an Early Bird draw for a private tour.

A 5 Peaks trail event at Heart Lake Conservation Park featuring shaded trails, a heart-shaped lake and four distance options. The race is cup-free with on-course aid stations and awards handed out on site.

A lake loop trail event at Christie Lake Conservation Area on October 10, 2026 featuring distances from 5 km to 53 km, cup-less aid stations and race kits, with proceeds supporting Oceana Canada.

Trail race on a 2.5 km loop at Camp Heidelberg in Waterloo on October 17, 2026 with options up to 50 km plus a 6 hour event and a 6 hour relay. The race is sanctioned by Athletics Ontario and raises funds for Run Walk Roll for WRHNCC.

Point to point trail race from Burlington to Dundas along the Iroquoia section of the Bruce Trail with 10 km and 25 km options. Bus transfers, aid stations, a race kit and parking for participants are included.

Trail races at Hilton Falls with 10 km, 25 km and 50 km options on varied single and double track. Sanctioned by Athletics Ontario, with planned aid stations, event apparel, and finisher medals.

Join the second annual trail run through Lions Valley in Oakville. Choose a 5 km or 11 km distance to honor veterans and support Wounded Warriors Canada.

A winter solstice trail event at Marydale Park featuring an approximately 3.7 km loop, multiple time-based race options including a relay, aid station provisions, finisher medal and proceeds for Hamilton Out Of The Cold.

A winter obstacle race at Albion Hills with a snowy 5-6 km course and 14 obstacles, finish-line hot chocolate and a metal finisher medal. Family discounts apply and a Polar Rush buff is included.