Trail Running calendar near Pickering 2025-2026

Hit the trails at the Long Sault Trail Race & Ultra on October 18, 2025, with options from a 2K kids fun run to a 6 hour loop challenge across scenic all trail loops. Fundraising supports CLOCA and every runner receives custom Outway socks.

Event details The Horseshoe Valley Hustle takes place on October 18, 2025 at Horseshoe Valley Resort in Barrie, Ontario. The event offers three distances: 1KM Small Steps Run/Walk (out-and-back on paved paths) 5KM trail race (one loop) 10K..

Join Head for the Hills on October 18 in St Catharines and enjoy scenic trails through Short Hills Provincial Park with 10 km, 5 km and a 1 km kids run. Family friendly and raising funds for the Brain Injury Association of Niagara.

Event details The Trails & Tails Classic takes place on October 19, 2025 at Terra Cotta Conservation Area, 14452 Winston Churchill Blvd, Halton Hills, ON L7G 0N9. The event is organized by Canadian Canicross Sports and had 55 participan..

Run scenic Oak Ridges Moraine trails and toast your finish at Slabtown Cider at the 5 Peaks Cider Run. Distances from a free 1K kids' fun run to a 21 km Grit, plus great finisher items and cider make it a must do fall trail outing.

Time For A Wine Run at Marjim Manor in Appleton, New York, hosts the 4th Annual Haunted Halloween Run, a 3.3-mile single-loop race held entirely on the Winery at Marjim Manor and nearby property. The scenic course winds through groomed trai..

Event information The Bolton Rotary Haunted Hill Run is scheduled for October 26, 2025, at 14111 Hwy 50, Bolton, Ontario L7E 1Y6. The event lists 61 participants. Registration opens on September 5 on the event website and is free for all pa..

Enjoy scenic trails at the Beav Trail Race in Milton Ontario with 10, 25 and 50 km options around a reservoir and waterfall. Friendly aid stations, custom finisher medals and hoodies for longer distances.

Time For A Wine Run at Schulze Vineyard & Winery is a 3.25-mile trail run on Schulze Vineyards & Winery property in Burt, New York. The single-loop course travels along groomed trails and through the vineyards, offering scenic vineyard scen..

Oakville Remembrance Trail Run is held at Upper Middle Park in Oakville, Ontario, featuring an 11-kilometer trail course through Lions Valley. Promoted as the first annual event, it aims to honor veterans, first responders, and their famili..

Event overview The Golden Spike Trail Race takes place on December 6, 2025, at Crawford Lake Conservation Area, Conservation Road, Milton, Ontario. The event offers trail running through forest paths and around Crawford Lake, including boar..

The Seaton Scramble Trail Race will take place in Pickering on Saturday 9 May 2026.

The Whole Enchilada is a trail running race held at Trail Hub in Uxbridge, Ontario, in Canada’s trail capital, Durham Region. It offers multiple distances: The Full Enchilada (50 km), Half Enchilada (25 km), Mini Enchilada (8 km), Hike Ench..

Timber24 is a 24 hour trail running festival near Barrie where teams of eight or four run an 8 km lap each hour to tackle 192 km together. Camp onsite, refuel with round the clock food and enjoy a Saturday night beer garden.

The Beav Trail Race 2026 The event takes place on Saturday, October 31, 2026, at Hilton Falls Conservation Area in Milton, Ontario. The event is sanctioned by Athletics Ontario. La Sportiva will provide a demo fleet of shoes and will give a..