Trail Running calendar near Distillery District 2026-2027

Spartan obstacle weekend at Brimacombe near Toronto and Lake Ontario offering Sprint 5 km, Super 10 km, a Kids Race and a 4 hour Hurricane Heat. Trail courses include 92 meters of climbing and multiple switchbacks.

A looped trail weekend in Ancaster offering 10K to 100 mile events on 20 km loops with over 500 m elevation per loop and four aid stations. The 100K and 100 mile races offer Western States qualifying opportunities.

Trail races from 5 km to a new 100 km solo or relay at Mansfield Outdoor Centre, with cupless aid stations, on-site camping and race services.

A 100 miles ultradistance route that circles the City of Hamilton starting in Carlisle. Finish the whole route within 40 hours for a gold buckle or spread the distance across June to earn a pewter buckle.

A 5 Peaks Ontario Trail Running Series race at Crawford Lake Conservation Area with distances from 1 km kids races to an 18.4 km Grit run. The site features reconstructed Indigenous longhouses and on course aid stations; spectators are welc..

A 38th annual trail event in St. Catharines featuring a 21.1 km half marathon and a 7 km trail race with limited fields. The routes include the 12 Mile Creek Trail and Hydro Hill and support the Niagara Rankin Cancer Run.

Community trail race in Streetsville along tree covered river paths. Offers a 1 km fun run for families and a chip timed 5 km; proceeds partly support Camp Wanago and an optional technical race shirt is available.

Hope in Motion 2026 in Caledon East offers cycling routes and 5 km and 10 km trails for walking, running, or rolling while raising funds for CMHA Peel Dufferin mental health and addictions services.

A trail race at Earl Rowe Provincial Park on June 13 2026 offering distances from 6K to 62K plus a Canadian virtual option. Mostly flat 12K loop, aid stations, cup free policy and a custom finisher medal.

Commemorative run in Niagara-on-the-Lake honoring General Józef Haller and the Blue Army, with races from 1 km to 10 km along the Niagara Parkway Recreational Trail. Race kit items, finisher medal and a prize draw for a flight to Poland.

A checkpoint-style trail race in Toronto on June 13, 2026, organized by Slowpokes with The North Face, featuring an approximately 10-15 km route, checkpoint navigation, and a morning post-race party with coffee, food, DJs and prizes.

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 running at Trail Hub in Uxbridge on 20 June 2026, with distances from a 1 km kids fun run to a 50 km end-to-end route, marked trails, aid stations and sustainability measures.

A timed 15:23 trail event at Marydale Park featuring an approximately 3.7 km loop, a relay option for teams up to five, one aid station per loop and race kit gels and a finisher medal. The event is listed as sold out.

Trail event on June 27, 2026 at Kelso Conservation offering 5K, 10K, MAX Elevation, 20K relay and kids options. The course uses roughly 3 km loops with notable elevation, aid stations and chip timing.

Trail races on the Toronto Bruce Trail near Milton, ON with 51.8 km and 27.5 km point-to-point options plus a hilly 10 km out-and-back. Technical singletrack on white-blazed routes, shuttle from Kelso, and a 200-person field limit.

Trail races at Area 8 Conservation Area on July 18 offering distances from kids 1 km to a 24.2 km Grit Run, with maps, aid stations and onsite awards for top finishers.

A 5K trail run at Bella Rose Vineyard in Lewiston, NY on July 19, 2026 offering a stemless wine glass and complimentary wine tasting for those 21 and older, professional timing, post-race snacks, and vineyard views.

Trail races at Dundas Valley Conservation Area offer a 7 km loop with rolling hills and about 130 m elevation per lap, multiple distance and timed formats, and an elimination Gong Show.

Beast of Burden Summer in Lockport NY follows the Erie Canal towpath and offers 100 mile, 50 mile and 25 mile distances with fully stocked aid stations and a start at Wide Waters Marina.