Trail Running calendar near Pickering 2025-2026

The Bella Rose Vineyard Wine Run 5k is a scenic running and walking event held at Bella Rose Vineyard & Winery in Lewiston, New York, along the Niagara Wine Trail. Scheduled for July 20, 2025, this chip-timed 5k race welcomes participants aged 1 to 99 and offers a festive atmosphere combining fitnes..

Timber24 Relay is a 24-hour trail running festival held at Hardwood Ski and Bike in Oro Medonte, near Barrie, Ontario. Teams of 4 (ultra) or 8 runners collectively cover 192 km by running 8 km laps each hour over 24 hours. The event features a lively atmosphere with on-site camping, a retail and exp..

The 5 Peaks Cider Run is a trail running event held at Slabtown Cidery and Woodnewton Farm in Uxbridge, Ontario, set amidst the scenic Oak Ridges Moraine. Celebrating the fall apple harvest, the race offers a variety of distances including a 1K kids' fun run, 3K kids' timed run, and adult options of..

The Beav Trail Race is an annual trail running event held at Hilton Falls Conservation Area in Milton, Ontario, Canada. The race features three distances: 10km, 25km, and 50km, with the 50km being two loops of the 25km course. The course is known for its fast, groomed trails combined with technical..

The Golden Spike Trail Race is a winter trail running event held at Crawford Lake Conservation Area in Milton, Ontario, Canada. Scheduled for December 6, 2025, it offers three distances: 5K, 10K, and 21K, catering to all levels from beginners to seasoned trail runners. The course features scenic, sn..