Trail Running calendar near Caledon 2026-2027

Experience one of the fastest trail races in Canada on the flat and groomed paths of Dundas Valley. Choose from distances between 5 km and 50 km in this scenic community event.

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.

A multi‑distance trail running event at Kelso Conservation Area on May 2, 2026, with courses from a free 1 km kids event to a 21 km Grit race. Multiple categories and variable fees, plus fundraising options.

Trail race in Cambridge Ontario on May 9, 2026 offering 12.5 km, 25 km, 50 km, a 12 hour event and a team relay. Races use repeated 6.25 km loops and the event includes fundraising for KidsAbility.

Seaton Scramble Trail Race offers distances from a 1K kids run to a 50K double loop on the Seaton Trail in Pickering. The marked course includes single and double track, a creek crossing, stairs and aid stations.

A chip timed 4 km on Cambridge’s Mill Run Trail on May 16, 2026. The certified crushed gravel course is an out and back with parking at Riverside Park and reusable chip timing.

Experience Ontario oldest ultra trail event in the scenic Dundas Valley. Run through Carolinian forests on a challenging multi loop course with distances ranging from 10 km to a WSER qualifying 100 mile solo race.

A fundraising trail event at Bechtel Park offering 5K and 2.5K options with or without dogs plus a 200 m Pup Run. Fundraising tiers unlock event apparel and swag.

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.

A 100 miles route circling the City of Hamilton through six communities. Finish within 40 hours for a Gold buckle or complete the distance during June to receive a Pewter buckle.

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.

A multi-distance trail event along Bruce Trail sections near Blue Mountains offering a 200 mile out and back, a point to point 100 mile and a 72.5 km E2E with multiple aid stations and mandatory gear requirements.

A trail loop event at Earl Rowe Provincial Park on June 13, 2026 offering distances from 6K to 62K, aid stations, cup-free support with a SpeedCup, and finisher medals.

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.

Trail Hub in Uxbridge hosts a trail event with distances from 1 km to 50 km across Durham Region forest trails. Courses are supported by aid stations and include environmental measures and local donations.

A 15 hour 23 minute looped trail event on an approx. 3.7 km circuit at Marydale Park with a relay option for teams up to five, a single aid station per lap, and proceeds supporting the C.Y.O. One-to-One camp program.

Backyard Ultra at the Tiffin Centre on June 27-28, 2026 featuring one loop every hour until one finisher remains. Fixed 6, 12, and 24 hour options on a mostly crushed gravel loop with camping and aid.

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.

A 5K obstacle event at Victoria Park in Kitchener on July 11, 2026, featuring 25+ obstacles and 2.5 million cubic feet of foam. Festival features include a free kids zone, live DJ, food vendors and a licensed beer garden.