Trail Running calendar near Alliston 2026-2027

Experience a technical trail run through the scenic Caledon Hills Bruce Trail with choices of 25 km, 50 km, or a full 72 km traverse ending at Mono Centre.

Experience a technical trail race through Ontario's beautiful Copeland Forest with 12.5 km, 25 km, and 50 km options. Support local mental health initiatives while tackling challenging climbs and unpredictable spring conditions.

Explore the scenic and technical trails of Kelso Conservation Area with distances ranging from 1 km to 20.6 km. This cup free trail event offers a unique outdoor challenge for runners and hikers of all ambitions.

Explore the scenic Seaton Trail in Pickering with distances from 1 km to 50 km. Enjoy a course featuring creek crossings, stairs, and hills with options for both trail runners and hikers.

Test your limits on the single track trails of Dufferin County Forest with distances ranging from 5 km to a 100 km ultramarathon available for solo runners and relay teams.

Test your endurance in Midland Ontario where runners complete a 6.706 km loop every hour until only one remains. Experience a relentless trail challenge that continues as long as you can answer the bell.

Experience the beauty of Crawford Lake Conservation Area with trail races ranging from 1 km to 18.4 km. Run through historic grounds featuring reconstructed Indigenous Longhouses in this professional cup free event.

A fundraising event by CMHA Peel Dufferin in Caledon East on June 7, 2026, offering 25 to 100 km cycling routes and 5 km/10 km trail options for adults and children, with event items and fundraising for mental health services.

Test your limits at The Ribbon 200 along Ontario's historic Bruce Trail with distances ranging from 72.5 km to 200 miles. Experience a point to point wilderness challenge featuring technical terrain and full support stations.

Join the fifth annual Rainbow Trail Run at Earl Rowe Provincial Park featuring scenic lake loops from 6 km to 62 km on a beginner friendly trail course.

Two trail-and-road runs in Uxbridge : 10 km and 5 km : starting and finishing at Elgin Park. A fundraiser for the new Uxbridge Hospital, with online registration open Feb 1 to June 10, 2026.

Experience an iconic trail race through Ontario s extensive forest networks with distances ranging from 1 km to 50 km. Join a community focused and eco friendly event in the heart of Canada s trail capital.

Utopia Backyard Ultra at Tiffin Centre runs June 27 to 28, 2026 with one lap every hour on a 4 miles 880 feet loop. Options include open ended Backyard and fixed 24, 12, and 6 hour formats.

Trail running event at Kelso Conservation on June 27, 2026 offering 2K, 5K, 10K, MAX Elevation and a 20K relay. Courses include aid stations, professional chip timing and a post event village with awards.

Experience an epic mountain run through Blue Mountain Resort featuring a timed 700 foot ascent and diverse trail distances from 1.5 km and 5 km to a 50 km ultra.

Experience an authentic point to point adventure along the historic white blazes of the Bruce Trail. Navigate technical terrain and stunning conservation areas in this small community focused trail race.

Experience a unique 5 km fun run at Wasaga Beach featuring over 25 obstacles and massive amounts of foam. Enjoy a festive atmosphere with music and activities suitable for all ages and fitness levels.

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 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.

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.