Trail Running calendar near Mississauga 2026-2027

Open water swims, an individual and relay swimrun, and 5K and 10K trail runs along the Welland Recreational Canal on August 2, 2026.

Relay race in Toronto where pre-formed mixed gender teams of four run as many laps as possible in 45 minutes; top five teams advance to a final decided by fastest laps.

Eight stage 80 km multi discipline running event in Ontario combining road, time trial, cross country, trail and track from August 9 to 16, 2026.

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 foam filled 5K with 25 plus obstacles and a festival atmosphere at Dagmar Ski Resort near Uxbridge Toronto, including a free Kids Fun Zone.

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 event at Albion Hills Conservation Area on September 5, 2026 offering multiple course categories and kids races.

Trail races at Albion Hills Conservation Park on the Humber River with multiple distances, camping, a pool and on course aid stations.

Backyard Ultra at Woodbine Beach Park with 6.71 km loops, an hourly elimination format, a 15-hour endurance option, and a one-Yard community waterfront run.

Family oriented survival style challenge in Mississauga with activities for adults, kids and dogs; on site at Paramount Fine Foods Centre, tickets CAD 40.54 to 107.64.

Trail 5 km at Bechtel Park on September 13, 2026, chip timed with reusable chips and minimal extras, free for Run Waterloo members.

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.

Fundraising run at Kiwanis Park supporting the Pediatric Oncology Group of Ontario with timed 5 km and 10 km races, a kids 200 m event, shirts and finisher medals.

Trail races at Slabtown Cider Co. on private Woodnewton Farm trails, multiple distances, local food and cider after the event, and fundraising for trail stewardship.

Fundraising trail event in Cambridge offering a walk, a hike or a 5K run along the Grand Trunk Trail with education stations, music and a BBQ at the ECO Centre.

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.

Backyard ultra at Albion Hills with two alternating 6.7 km loops offered as 24 hour solo, 24 hour relay two person, 12 hour and 6 hour formats.

A recreational 5K trail run and walk on September 26, 2026 at Strom’s Farm and Bakery in Guelph featuring a cedar spiral, corn maze sections, dirt paths and post run treats.

A chip-timed, transit-friendly trail race in King’s Forest, Hamilton on September 27, 2026, offering distances from kids runs to a 21 km Bruce Trail course, aid stations and a Canadian made toque.

A 5K trail run with a 1K option at The Donkey Sanctuary of Canada on September 27 2026 supporting care for donkeys and mules.