Trail Running calendar near Pickering 2025-2026

2025 5 Peaks Trail Running Series: Heart Lake is held at Heart Lake Conservation Area, Heart Lake Road, Brampton, Ontario. The fifth event in the Ontario edition takes place on Saturday, October 4, 2025. It offers multiple trail distances, with options adjustable via a Change Distance feature; check..

The Ramblers Run is a fitness-forward, family-friendly event among the vines at Palatine Hills Estate Winery in Niagara-on-the-Lake, Ontario. Participants can choose a 1.25 km family walk/run, a 5 km race, or a 1.25 km dog walk, with grass and dirt paths and some uneven terrain suitable for walkers,..

Head for the Hills Trail Race returns to White Meadow Farms in St. Catharines, Ontario. Participants can choose from a 10 km Run, a 5 km Walk/Run, or a 1 km Kids Run, with virtual equivalents available.The course runs through Shorthills Provincial Park and finishes back at the White Meadow Farms pro..

Horseshoe Valley Hustle is a trail race held at Horseshoe Valley Resort in Barrie, Ontario. The event offers 5 km and 10 km trail distances, with a Small Steps 1 km Run/Walk for youngsters and families. The course is rugged and technical, featuring narrow forest trails, frequent elevation changes, a..

Long Sault Trail Race & Ultra is a community trail-running event at Long Sault Conservation Area, Woodley Road, Bowmanville, Ontario. Distance options are 7K, 14K, 21K, or a 6-hour ultra. The course uses two 7K loops: 7K runners complete one loop, 14K runners do both loops, and 21K runners do both l..

The Cider Run is a trail running event held at Slabtown Cider Company / Woodnewton Farm in Uxbridge, Ontario on Saturday, October 25, 2025. The course uses trails on the Oak Ridges Moraine and routes and distances may be changed based on trail conditions. Slabtown Cider Co. will be open on race day..

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 trails and Bittner/Singer apple orchards, offering a festive Hal..

The Beav Trail Race is a multi-distance trail running event held at Hilton Falls Conservation Area near Milton, Ontario, Canada. Distances include 10 km, 25 km, and 50 km, with the 50 km run as two laps of the 25 km course. The 10 km is an out-and-back to the waterfall on groomed trails with a short..

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 scenery. Runners receive a custom race shirt, professional timin..

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 families. The atmosphere is described as a remembrance movement, i..

The Golden Spike Trail Race is a winter trail running event at Crawford Lake Conservation Area in Milton, Ontario. Participants choose from 5K, 10K, or 21K, dashing through snowy forest, a boardwalk around the lake, and rugged Bruce Trail sections by a canyon. The course blends fast main-trail segme..

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 Enchilada (4 km), plus Kids Enchilada (4 km) and Kids Salsa (1 k..