Trail Running calendar near Distillery District 2026-2027

A 7 km loop trail event in Dundas Valley offering formats from one loop to 100 miles plus timed races and on-course aid at the start finish.

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.

A summer ultramarathon on the Erie Canal towpath in Lockport NY offering 100 mile, 50 mile and 25 mile options. The course starts at Wide Water's Marina and includes multiple staffed aid stations and a Middleport turnaround.

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 event at Albion Hills Conservation Area in Caledon on September 5, 2026 offering multiple course and youth race options.

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.

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.

Trail event at Slabtown Cider Co., Uxbridge on September 19 2026, offering multiple distances, a kids run, a hike, fundraising and cup free practices.

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 featuring a cedar spiral, parts of the corn maze, and post event treats for participants.

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.

Trail event at the Donkey Sanctuary of Canada in Puslinch with 5 km and 1 km options, fundraising for sanctuary care on September 27, 2026.

Cross-country meet in Niagara Falls on September 27, 2026, featuring an Open 5K and separate morning and afternoon sessions; fees listed in CAD.

Trail races at Heart Lake Conservation Park on October 3 feature multiple distances from 3 km to 22.5 km on shaded trails with fall colour.