Trail Running calendar near Mississauga 2026-2027

Trail races at Kelso Conservation Area include kids 1 km and 3 km plus 6.9 km, 13.8 km and 20.6 km options. The cup-free event provides water at start, finish and aid stations and offers optional wooden finisher medals.

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.

Two days of trail racing in Ancaster on a 20 km loop offering distances from 10K to 100 miles. Four aid stations, a cup free policy, and status as a Western States 2027 qualifying 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.

Trail runs at Crawford Lake Conservation Area offer distances from 1 km kids races to an 18.4 km Grit Run. The site features three reconstructed Indigenous Longhouses and water stations; swag and medals are available for purchase.

An annual St. Catharines event supporting the Niagara Rankin Cancer Run, featuring a historic half marathon along 12 Mile Creek Trail and a 7 km trail race using the latter part of the course.

A community trail race in Streetsville with a 1 km fun run and a chip timed 5 km along the river. Part of proceeds support Camp Wanago.

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 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.

A commemorative run honoring General Józef Haller and the Blue Army with races from 1 km to 10 km in Niagara on the Lake. The route follows the Niagara Parkway Recreational Trail and includes an event t shirt and finisher medal.

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.

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.

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.