Trail Running calendar near Mississauga 2026-2027

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, six stages and 60 kilometres in the Conestogo and Waterloo area. A staged event across road, trail, cross country and track with capped registration and time limits.

Join the fourth race of the 5 Peaks Ontario West Series at the Area 8 Conservation Area. Experience trail running in Milton while supporting local charitable foundations.

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.

The ENDURrun is the ultimate test of endurance: 160 km across seven stages over eight days in August 2026. The challenge includes a half marathon, cross country, marathon, and time trials. Relay team and individual stage guest options are a..

Raid the City 2026 is a team event organized by DontGetLost Adventure Running with online registration via Zone4. Fees are $150 for adult teams and $50 for junior or family teams and deadlines apply.

A two day obstacle course event in Uxbridge with an approximate 5K route, 25 plus optional obstacles including a large inflatable waterslide and mud pits, plus festival amenities and a free kids zone for young children.

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 event at Albion Hills Conservation Park as part of the 5 Peaks Ontario series. Singletrack routes along the Humber River with multiple distances, aid stations and podium awards on site.

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..

Trail event at Slabtown Cider Co. on private Woodnewton Farm trails near Uxbridge. Multiple distances from a kids 1K fun run to a 40K five loop race and fundraising for local trail restoration.

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.

Trail running event at Heart Lake Conservation Area on October 3, 2026 offering multiple course options and kids races, with variable registration fees and fundraising partners.

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.

The Beav Trail Race at Hilton Falls on October 31 offers 10 km, 25 km and 50 km on fast but technical trails with scenic waterfall views. Bring your own cup or bottle as no cups are provided, and finishers earn a custom medal and apparel.

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.