Trail Running calendar near Milton 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, 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 staged days in Waterloo region combining road, trail, cross country and track into a cumulative 80 km multi-discipline event.

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.

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 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.

5 km run/walk and 10 km run at Kiwanis Park on September 19, 2026 supporting the Pediatric Oncology Group of Ontario.

Fundraising walk, hike and run on September 20, 2026 at Riverbluffs Park in Cambridge to support rare's land conservation.

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 style race at Willibald Farm Distillery & Brewery in Ayr on September 27, 2026 with a 2.5 km loop and 5 km and 10 km options. Proceeds support rare Charitable Research Reserve and the event is sold out.

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.