Trail Running calendar near Milton 2026-2027

Albion Ascent is a chip timed urban trail race in Hamilton with distances from 1 km kids to 21 km. Courses run through King's Forest and the Bruce Trail and include aid stations and a cupless policy.

Trail event at the Donkey Sanctuary of Canada in Puslinch on September 27, 2026. Features a 5K and a 1K option with proceeds directed to The Donkey Sanctuary of Canada.

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, with distances from a 3 km kids run to a 22.5 km grit course, shaded trails, aid stations on course, a cup free format and limited parking.

Looped trail races at Christie Lake on October 10, 2026 offering distances from 5 km to 53 km with a relay option. The event supports Oceana Canada and provides aid stations plus on course nutrition from a local supplier.

Trail event on October 17, 2026 at Camp Heidelberg in Waterloo ON. Run 2.5 km loops in distances from 5 km to 50 km, with 6 hour and relay options; proceeds support Run-Walk-Roll for WRHNCC.

Community run and roll on October 18, 2026 with 2 km, 6.5 km and 13 km routes, a costume contest with gift card prizes, required pre registration and finish line refreshments.

Point to point trail races of 10 km and 25 km along the Bruce Trail from Burlington to Dundas, finishing at Dundas Valley Conservation Area; bus transport to starts, aid stations, and limited to 180 entries.

A Halloween themed event in Waterloo on October 31, 2026 featuring a 5 km race, a 200 m fun run, a pre-race costume contest, medals for all, and a stroller passenger registration category.

Trail races at Hilton Falls on November 7, 2026 offering 10 km, 25 km and 50 km. The course combines groomed runnable trails and short technical sections and includes planned aid stations and charity support.

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 near Mount Hope with an approx 3.7 km loop and full, half, quarter and relay time options. The race is sanctioned by Athletics Ontario and benefits Hamilton Out Of The Cold.

A winter obstacle race at Albion Hills with a snowy 5-6 km course and 14 obstacles, finish-line hot chocolate and a metal finisher medal. Family discounts apply and a Polar Rush buff is included.