Trail Running calendar near Mississauga 2026-2027

Six day stage event totaling 60 km in the Waterloo region from July 13 to 18 2026. The program mixes road, time trial, cross country, technical trail, track racing and a half marathon.

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 race at Dundas Valley Conservation Area with a 7 km loop and options from a single loop to 100 miles plus 6 12 and 24 hour timed events. Aid station, cup free policy, medals and a 100 mile belt buckle.

Open-water swims, a swimrun and trail runs at the Welland Community Boathouse on August 2, 2026, with swims from 2K to 10K, an about 11 km swimrun and 5K and 10K trail options.

Eight days and eight stages totaling 80 km across road, trail, cross country and track in Ontario with a technical t-shirt and a finisher medal for those who complete all stages.

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 5 km obstacle event at Dagmar Ski Resort on August 29 and 30, 2026, with 25 plus obstacles, a foam zone using 2.5 million cubic feet of foam, a free Kids Fun Zone, live DJ and food vendors.

Raid the City is a three hour urban adventure run for teams of two in Hamilton. Teams use maps and a smartphone app to score checkpoints across trails, roads, alleys and parks while travelling on foot.

Trail running at Albion Hills Conservation Area in Caledon on September 5, 2026, offering multiple course types from kids events to longer enduro and grit options. Registration uses tiered fees in Canadian dollars with taxes and processing..

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 oriented survival style obstacle challenge at Paramount Fine Foods Centre in Mississauga. The event includes adults, kids and dogs and uses varied terrain with undisclosed obstacles. Tickets range from CAD 40.54 to CAD 107.64.

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 among the vines at Palatine Hills Estate Winery with a timed 5 km race, 1.25 km family routes and a dog walk, followed by food, drink, live music and awards.

A charity run and walk at Kiwanis Park with 5 km and 10 km timed courses plus a free 200 m kids race. The event supports the Pediatric Oncology Group of Ontario, includes finisher medals and technical shirts for early registrants.

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.

A loop-based endurance event at Albion Hills with solo, relay and team 24 hour options plus 12 hour and 6 hour formats. Runners complete repeated 6.7 km loops with one aid station at the start finish area.

A 5K trail run and walk at Strom’s Farm and Bakery in Guelph on September 26, 2026, with a route through a cedar spiral, corn maze sections, and field paths. Treats are provided and a fundraising pledge option is available.

Trail race in Hamilton with paved paths, dirt singletrack and waterfalls across distances from 1 km kids runs to 21 km. Aid stations are provided, a Canadian-made toque is included and medals are available as add-ons.