Trail Running calendar near Conestogo 2026-2027

Cross country style race at Willibald Farm Distillery & Brewery in Ayr on September 27, 2026 with a 2.5 km loop and 5 km and 10 km options. Proceeds support rare Charitable Research Reserve and the event is sold out.

Trail races at Heart Lake Conservation Park on October 3, with distances from a 3 km kids run to a 22.5 km grit course, shaded trails, aid stations on course, a cup free format and limited parking.

Looped trail race at Christie Lake on October 10, 2026 offering 5.3 km loops with distances to 53 km solo or relay. Aid stations, cup-less policy, timed results and fundraising for Oceana Canada.

Trail race at Camp Heidelberg on October 17, 2026 featuring 2.5 km loops with distance options from 5 km to 50 km, plus a 6 hour format and relay. Sanctioned event and fundraiser for Run-Walk-Roll for WRHNCC.

Community run and roll on October 18, 2026 with 2 km, 6.5 km and 13 km routes, a costume contest with gift card prizes, required pre registration and finish line refreshments.

A point to point trail race along the Iroquoia Section of the Bruce Trail between Burlington and Dundas. Two distances with aid stations, bus transport and limited registration to maintain a community feel.

A Halloween-themed run in Waterloo with a 5 km race, a 200 m fun run, a pre-race costume contest and finisher medals for participants.

Trail races at Hilton Falls on November 7, 2026 offering 10 km, 25 km and 50 km loops. Varied groomed and technical trails, cupless aid stations, apparel for longer distances and medals for finishers.

A trail running event in Oakville on November 7, 2026, offering 5 km and 11 km routes through Lions Valley, held in honour of veterans and first responders with proceeds to Wounded Warriors Canada.

Trail event at Mansfield Outdoor Centre offering 10 km, 5 km and a 1 km kids race, with hoodies, medals, chili and beer for adult distances. Cup free, on course aid and meals in the cafe, registration closes November 1 2026.

Trail event on a 3.7 km loop at Marydale Park offering full, half, quarter and relay options. One aid station per loop, all participants receive a crewneck and finisher medal, proceeds support Hamilton Out Of The Cold.

A winter obstacle race at Albion Hills with a snowy 5-6 km course and 14 obstacles, finish-line hot chocolate and a metal finisher medal. Family discounts apply and a Polar Rush buff is included.

Looped trail races in Dundas Valley on May 22, 2027 offer distances from 10K to 100 miles, regular aid stations and Western States qualifying opportunities.