Trail Running calendar near Mississauga 2026-2027

Trail races and challenges at Kelso Conservation on June 27 2026 include 5K, 10K, MAX Elevation, kids races, a 20K relay and an Energy Mile with $500 in prizes.

A 5 km obstacle run at Victoria Park in Kitchener on July 11, 2026 featuring more than 25 obstacles, a large inflatable waterslide and 2.5 million cubic feet of foam. Festival elements include a free Kids Fun Zone, live DJ and food vendors.

Trail races on the Toronto Bruce Trail with 50 km, 27.5 km and 10 km options, technical single track and shuttle service from Kelso. Aid stations, cup free format and a finisher medal for finishers.

A foam filled 5K at Victoria Park in Kitchener on July 11, 2026 featuring more than 25 obstacles and 2.5 million cubic feet of foam. The event includes a family festival with a Kids Fun Zone, live DJ and food vendors.

Six days and six stages totalling 60 km in Ontario from July 13 to 18, 2026. The event mixes road, cross country, trail and track racing with on-course support, a technical shirt and a finisher medal.

Trail races at Area 8 Conservation Area on July 18, held on trails around a former limestone quarry, with distances from 1 km for kids to 24.2 km and course maps and aid stations provided.

Trail event at Dundas Valley with a 7 km loop and multiple formats from a single loop to 100 miles plus 6 12 and 24 hour races. The race is sanctioned by Athletics Ontario and features partners La Sportiva and THN Labs.

Eight days and eight stages totaling 80 km around Conestogo, Waterloo and Cambridge from August 9 to 16, 2026. The event mixes road, cross country, trail and track with on course support, a technical shirt and a finisher medal.

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.

A two day 5K obstacle event at Dagmar Ski Resort featuring more than 25 obstacles, 2.5 million cubic feet of foam, a free Kids Fun Zone, live DJ, food vendors and a licensed beer garden.

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 at Albion Hills on September 5, 2026 with Sport, Enduro and Grit course options plus timed and free kids events; fees vary by course and registration period and taxes and processing fees apply.

Trail races at Albion Hills Conservation Park in Caledon with singletrack routes, distances from 7.5 km to 22.75 km, riverside camping and a nearby pool. Water and aid stations are provided and the event is cup free.

UNFINISHED is a Backyard Ultra at Woodbine Beach Park where runners repeat a 6.71 km loop each hour and decide how far to go. Event options include an elimination format, a 15 hour open challenge, and a single community loop.

A family adventure event in Mississauga on September 12, 2026 with courses for adults, children and dogs. Survival style challenges take place across varied terrain, obstacles are not revealed and tickets range from 40.54 CAD to 107.64 CAD.

A two-loop 5 km trail run at Bechtel Park in Waterloo on September 13, 2026, chip timed with reusable chips. Free for Run Waterloo members, standard entry listed as $15 plus fees.

A community run through the vines at Palatine Hills Estate Winery featuring a timed 5 km race, untimed family and dog walks, post-run food and music, and winery perks. A portion of proceeds supports Community Care.

Community timed 5 km and 10 km races plus a 200 m kids run at Kiwanis Park. The event raises funds for the Pediatric Oncology Group of Ontario and includes medals, limited technical shirts, and post-race refreshments.

Trail races and a hike take place on September 19, 2026 at Slabtown Cider Co and Woodnewton Farm, with distances from a 1K kids run to a 40K five loop race and fundraising elements.

A 5K trail run on Bella Rose Vineyard grounds in Lewiston with a stemless wine glass and complimentary wine tasting for participants 21 or older. The event features professional timing, finish line photos, music, and on site parking.