Trail Running calendar near Brampton 2026-2027

UNFINISHED is a Backyard Ultra at Woodbine Beach Park on September 12, 2026 featuring repeated 6.71 km loops. Options include Backyard Ultra solo or teams of three, a 15 hour Endurance window, and a community Sunshine Yard.

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.

Beat Bechtel is a certified two loop trail 5 km at Bechtel Park in Waterloo on September 13 2026. The chip timed event has minimal extras, is free to Run Waterloo members, and lists a base fee of $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.

A community fundraising run at Kiwanis Park on September 19, 2026 offering 5 km, 10 km, a 5 km walk and a 200 m kids race; courses run on park dirt trails with water stations and medals for finishers.

Trail races and hikes take place at Slabtown Cider Co on private Woodnewton Farm trails in Uxbridge, ON. Multiple distances range from a 1 K kids run to a 40 K five loop event and the hike donates part of its fee to trail restoration.

Loop based backyard ultra at Albion Hills with two alternating 6.7 km loops over mixed trail terrain. Multiple formats include solo, two person relay, two person team, 12 hour and 6 hour options.

A chip timed trail event in Hamilton with distances from 1 km kids runs to a technical 21 km on the Bruce Trail. Cupless aid stations, included Canadian toque and optional medals for purchase.

A trail event at the Donkey Sanctuary of Canada on September 27, 2026 offering a 5 km and a 1 km option, fundraising for the sanctuary. Registration fee is CA$40 per entry.

A cross country style race on a 2.5 km pasture loop at Willibald Farm Distillery & Brewery, with 5 km and 10 km options. Proceeds support the rare Charitable Research Reserve and participants receive curated goods and official timing.

Trail races at Heart Lake Conservation Park on October 3, with distances from a 3 km kids run to a 22.5 km Grit course. Shaded trails, aid stations, a no‑cup policy, and limited parking; awards must be collected at the event.

Trail event at Christie Lake with a 5.3 km loop and distances from 5 km to a 53 km solo or relay. Aid stations use no disposable cups, finishers receive medals, and the event supports Oceana Canada.

A mixed gravel road and trail loop in Creemore offering 14K, 27.5K, 55K and 80K/50M options with multiple laps, aid stations, finish items, and photography provided after the race.

Trail race on a 2.5 km loop at Camp Heidelberg on October 17, 2026. Distances from 5 km to 50 km plus 6 hour individual and relay options, chip timed and raising funds for Run Walk Roll for WRHNCC.

Point to point trail races of 10 km and 25 km along the Iroquoia Section of the Bruce Trail between Burlington and Dundas. Courses are marked, include aid stations and parking at Dundas Valley Conservation Area is included.

Trail distances and an eight hour endurance challenge take place at Horseshoe Valley Resort on October 31, 2026. Options include 1 km, 5 km, 10 km and an 8 hour solo or team challenge on a rugged 5 km loop.

Trail races at Hilton Falls near Milton, ON with 10 km, 25 km and 50 km options. The route mixes groomed runnable trails and technical single track, with planned aid stations, event apparel and finisher medals.

A trail running event in Oakville on November 7, 2026, offering 5 km and 11 km routes through Lions Valley, held in honour of veterans and first responders with proceeds to Wounded Warriors Canada.

Trail event at Mansfield Outdoor Centre offering 10 km, 5 km and a 1 km kids race, with hoodies, medals, chili and beer for adult distances. Cup free, on course aid and meals in the cafe, registration closes November 1 2026.

A winter solstice trail event at Marydale Park featuring a 3.7 km loop and Full, Half, Quarter or relay formats. Aid station every few kilometres, finisher medal and crewneck included, and proceeds support Hamilton Out Of The Cold.