Trail Running calendar near Bolton 2026-2027

Experience a technical trail race through Ontario's Beaver Valley featuring waterfalls and steep climbs. Choose between a marathon, half marathon, or the two day Bruce Deuce challenge.

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.

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.

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.

Join a community tradition at Kiwanis Park for the 13th anniversary of this charity run featuring 5 KM and 10 KM trail routes and a special kids dash.

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.

Experience Ontario's only three day stage race at Blue Mountain Resort. Challenge yourself with a vertical climb, an ultra distance classic, and a strategic timed loop race in one weekend.

Transit-friendly, chip-timed trail race in Hamilton offering 1 km, 5 km, 10 km and 21 km on paved paths, dirt trails and technical singletrack through forests, waterfalls and the Bruce Trail.

A 5k trail run through the scenic fields of the Donkey Sanctuary of Canada in Puslinch. A 1k route is also available. This fundraising event takes place on September 27, 2026.

Part of the 5 Peaks Ontario series at Heart Lake Conservation Park, offering distances from 3 km to 22.5 km on shaded trail routes with course maps and aid stations, and a cup free policy.

Race through a beautiful looped trail course at Christie Lake Conservation Area. With distances ranging from 5 km to a 50 km solo or relay, there is an option for every trail runner.

Event Overview The Creemore Vertical Challenge takes place on October 17, 2026. It is a trail and ultrarunning event offering four different race distances: 14 km, 27.5 km, 55 km, and 80 km (50 Miler). The course is a combination of trails..

Experience a forest trail race at Camp Heidelberg with loop based distances ranging from 5 km to 50 km plus a 6 hour solo or relay challenge.

Experience a point to point adventure along the historic Bruce Trail from Burlington to Dundas. This sanctioned trail race offers technical terrain and scenic escarpment views with shuttle transport provided for all runners.

The Beav Trail Race at Hilton Falls on October 31 offers 10 km, 25 km and 50 km on fast but technical trails with scenic waterfall views. Bring your own cup or bottle as no cups are provided, and finishers earn a custom medal and apparel.

Join the second annual trail run through Lions Valley in Oakville. Choose a 5 km or 11 km distance to honor veterans and support Wounded Warriors Canada.

Experience a premier winter obstacle run featuring a 5 to 6 km snowy course at Albion Hills. Tackle over 14 challenges like snow crawls and tubing while enjoying themed waves and festive finishers rewards.