Trail Running calendar near Caledon 2026-2027

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 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.

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.

Community timed 5 km and 10 km races plus a 200 m kids run at Kiwanis Park. The event raises funds for the Pediatric Oncology Group of Ontario and includes medals, limited technical shirts, and post-race refreshments.

Trail races and a hike take place on September 19, 2026 at Slabtown Cider Co and Woodnewton Farm, with distances from a 1K kids run to a 40K five loop race and fundraising elements.

A three-day stage trail race at Blue Mountain Resort featuring a steep 5 km opener, a 25/50 km cross-country day, and a timed 3-hour loop finale, with daily podiums and overall Big Bully and Little Bully awards.

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 5K trail run and walk at Strom's Farm and Bakery in Guelph on September 26, 2026, featuring a cedar spiral, parts of a corn maze and field trails. Includes on-site facilities, a paid activity area option and fundraising tiers with rewards..

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.

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.

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.

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 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.

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.

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.

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.