Trail Running calendar near Mississauga 2026-2027

Trail races at Crawford Lake Conservation Area offer distances from 1 km kids runs to 16.7 km Grit and include three reconstructed Indigenous longhouses on site. Routes for 2026 may be modified due to construction.

Trail event in St. Catharines on June 6, 2026 offering a 21.1 km half marathon and a 7 km trail race on a historic route that includes Merritt Trail, 12 Mile Creek Trail and Hydro Hill, supporting the Niagara Rankin Cancer Run.

Community trail race in Streetsville along tree covered river paths. Offers a 1 km fun run for families and a chip timed 5 km; proceeds partly support Camp Wanago and an optional technical race shirt is available.

CMHA Peel Dufferin's fundraising event in Caledon East features 25, 50 and 100 km cycling routes plus 5K and 10K trail options. Registration includes a jersey or t shirt, food and a free on site celebration with entertainment.

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.

Two trail-and-road runs in Uxbridge : 10 km and 5 km : starting and finishing at Elgin Park. A fundraiser for the new Uxbridge Hospital, with online registration open Feb 1 to June 10, 2026.

Trail running event at Trail Hub in Uxbridge offering multiple distances from 50 km down to a 1 km kids run. The event features marked trails, aid stations and environmental giving with a cup free policy.

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 5K trail run at Bella Rose Vineyard in Lewiston, NY on July 19, 2026 offering a stemless wine glass and complimentary wine tasting for those 21 and older, professional timing, post-race snacks, and vineyard views.

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.