Trail Running calendar near Caledon 2026-2027

Trail races on the Toronto Bruce Trail near Milton Ontario with about 52 km, 27.5 km and 10 km options. Point-to-point courses use white blazes, include shuttle service and spaced aid stations.

A 5 kilometre obstacle run at Victoria Park in Kitchener on July 11 2026 with more than 25 obstacles and 2.5 million cubic feet of foam. The event includes a free kids fun zone, live DJ, food vendors and a licensed beer garden.

Six days, six stages and 60 kilometres in the Conestogo and Waterloo area. A staged event across road, trail, cross country and track with capped registration and time limits.

A 5 km obstacle course at Wasaga Beach with over 25 optional obstacles, a free kids zone for ages 6 and under and event fundraising for Make-A-Wish Canada.

Join the fourth race of the 5 Peaks Ontario West Series at the Area 8 Conservation Area. Experience trail running in Milton while supporting local charitable foundations.

Experience a diverse trail event in Hamilton featuring loop-based distances from 7 km to 100 miles and unique timed elimination challenges.

A trail event on the Beaver Valley section of the Bruce Trail offering a 42 km marathon, a 21 km half, and a double-race option. Expect rocky, rooty single-track, significant elevation, sparse aid stations, and an 11-hour marathon cutoff.

The ENDURrun is the ultimate test of endurance: 160 km across seven stages over eight days in August 2026. The challenge includes a half marathon, cross country, marathon, and time trials. Relay team and individual stage guest options are a..

Test your limits on the rugged Bruce Trail with technical courses ranging from 16 to 66 km at the Devil's Glen Country Club. Experience steep climbs and unique landmarks in this sanctioned Ontario trail event.

A 24 hour trail running festival at Hardwood Ski and Bike in Oro Medonte on August 22-23, 2026. Teams of 8, 4, 2 or solo runners take turns on 8 km hourly laps while a camping village, food service and evening events run alongside.

Raid the City 2026 is a team event organized by DontGetLost Adventure Running with online registration via Zone4. Fees are $150 for adult teams and $50 for junior or family teams and deadlines apply.

A two day obstacle course event in Uxbridge with an approximate 5K route, 25 plus optional obstacles including a large inflatable waterslide and mud pits, plus festival amenities and a free kids zone for young children.

Join the third race of the 5 Peaks Ontario Series at the Albion Hills Conservation Area in Caledon. Support great causes while running through beautiful Ontario trails on September 5 2026.

Trail running at Albion Hills Conservation Park with singletrack trails along the Humber River. Three distance options with maps, aid stations and on site awards; swag and finisher medals available for purchase.

A chip timed trail race at Bechtel Park in Waterloo on September 13, 2026. The certified 5 km runs as two loops with limited services and free entry for Run Waterloo members.

A community fundraising run at Kiwanis Park in Kitchener on September 19, 2026 offering 5 km, 10 km and a kids 200 m. The event benefits the Pediatric Oncology Group of Ontario and includes a technical t-shirt for early registrants and fini..

Trail event at Slabtown Cider Co. on private Woodnewton Farm trails near Uxbridge. Multiple distances from a kids 1K fun run to a 40K five loop race and fundraising for local trail restoration.

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.

A transit-friendly, chip-timed urban trail race in Hamilton offering multiple distances through King's Forest, the Bruce Trail and scenic waterfalls. Aid stations are cupless and a Canadian made toque is included.

A 5 km trail run with a 1 km option at the Donkey Sanctuary of Canada in Puslinch on 27 September 2026, supporting sanctuary fundraising. Listed fee CA$40 and teams registered by 31 July enter an Early Bird draw for a private tour.