Trail Running calendar near Milton 2026-2027

A flat chip timed 5 km on Hamiltons waterfront at Bayfront Park on March 28 2026, with a finisher medal, post race food and online photos. Early registrants receive a hooded sweat top and awards are given overall and by five year age groups..

Trail event on the Caledon Hills Bruce Trail offering 25 km, 50 km and 72 km end to end options finishing at Mono Centre Park. Courses follow white blazes with technical singletrack, climbing and seven aid stations; bus transport is provide..

Trail race at Dundas Valley Conservation Area offering 5 km to 50 km out-and-back courses on a near-flat, groomed rail trail with aid stations every 5 to 8 km, chip timing, shirts and finisher medals. Event supports Melanoma Canada.

Trail races at Kelso Conservation Area feature forested routes with climbs and descents. Distances range from 1 km to 20.6 km with a cup free format, aid stations and optional wooden finisher medals.

Trail race on the Seaton Trail near Pickering with distances from a 1K kids run to a 50K double loop. The out and back course is well marked and includes single and double track, a creek crossing, stairs and a nine hour cutoff.

A two day trail weekend in Dundas Valley featuring 20K loop races from 10K to 100 Mile, four aid stations, team relays and Western States qualifying opportunities.

Tails on Trails is a community fundraising trail run supporting the local Humane Society. Choose from timed 5K or untimed 2.5K events, with options to run with or without your dog, all within Bechtel Park. Fundraising is encouraged, with pr..

The Great Mansfield Outdoors is a trail run on the single-track paths of Mansfield Outdoor Centre and Dufferin County Forest. A new 100 km solo and relay distance debuts in 2026. This cup-free event offers races from 5 km to 100 km, with on..

A 100-mile route around the City of Hamilton starting in Carlisle on May 30, 2026. Finish within 40 hours for a Gold buckle or complete the distance during June to receive a Pewter buckle.

A trail half marathon of 21.1 km and a 7 km trail race through historic parts of St. Catharines including the 12 Mile Creek Trail. Limited fields and a walker division that uses the same route.

Join Hope in Motion 2026 on June 7 in Caledon East for a community fundraiser supporting CMHA Peel Dufferin with cycling, walking, running and rolling for all abilities. Choose distances from 5 km trails to 100 km rides and help raise funds..

Trail event on June 13, 2026 at Earl Rowe Provincial Park in Alliston offering looped distances from 6K up to 62K plus a 12K virtual option. Mostly wide trail with varied surfaces, aid stations, cup free service and a finisher medal.

Time based trail event on June 20, 2026 at Marydale Park using a 3.7 km loop, offered as a 15 hour 23 minute solo format or a team relay for up to five runners, with one aid station, shirt and medal and funds to the C.Y.O. 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.

Trail races along the Toronto Bruce Trail on July 11, 2026, offering approx. 52 km, 27.5 km and 10 km options, point to point courses with shuttle service for longer distances and cup free aid stations.

The ENDURrun Prelim is a unique six-day, six-stage running challenge covering 60 km. It tests runners on varied terrain including road, cross-country, trail, and track, culminating in a half marathon. Participants receive a tech t-shirt and..

The fourth 5 Peaks event in Ontario is at Area 8 Conservation Area, with routes from 1 km kids races to a 24.2 km Grit Run, mapped aid stations, parking, washrooms, and a cup-free policy.

Trail running at Dundas Valley Conservation Area with a 7 km loop, timed 6 12 24 hour races, a 100 mile option, a 21 km race and the Gong Show elimination event. The course is wooded with rolling hills and about 130 m gain per lap.

The ENDURrun Sport is an eight-day, 80 km stage race across Waterloo Region. It features eight unique stages, from a 10k road race to a trail run and a track event. Runners test themselves across varied terrain over a full week of competiti..

The 5 Peaks Albion Hills trail run takes place in the scenic Albion Hills Conservation Park. With distances from 7.5 km to 22.75 km, it offers singletrack trails and family-friendly activities like camping and a pool.