Trail Running calendar near Bolton 2025-2026

Event details The Pace for the Donkeys event is a trail run held on September 28, 2025, at the Donkey Sanctuary of Canada, 6981 Concession Road 4, Puslinch, Ontario. The event offers two course options: 5 km trail run 1 km route option On..

Albion Ascent Trail Race : Overview The Albion Ascent Trail Race is a chip-timed urban trail event in Hamilton, Ontario. The course mix includes paved paths, dirt trails and technical singletrack. Routes pass rivers, waterfalls and forested..

The Blue Bully Ultra is Ontario's only three-day stage trail running race held at Blue Mountain Resort, featuring a weekend festival of running and fun from October 3-5, 2025. The event offers three race styles: The Stampede, a fast 5km wit..

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,..

Sticks n' Stones Trail Race 2025 is held at Christie Lake Conservation Area in Hamilton, Ontario. All races follow a single rolling dirt loop around the lake, about 5.3 km per lap. Distances offered: 5 km (1 loop), 10 km (2 loops), 26.5 km..

Wise Raven Trail Race is held at Camp Heidelberg in Waterloo, Ontario. The fundraiser offers multiple distances: 5 km (2 loops), 10 km (4 loops), 25 km (10 loops), 50 km (20 loops), and a 6-hour relay. Runners follow a 2.5 km forest loop ar..

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..

Creemore Vertical Challenge 2025, in Creemore, Ontario, at Mad River Park, is a multi-distance ultramarathon organized by North of 89 Outdoors. Runners choose from four distances: 14K, 27.5K, 55K, and 80K (50 miles). The 80K/50M is three la..

Hike 4 Horses is a fundraising community event held at Sunrise Therapeutic Riding & Learning Centre in Puslinch, Ontario. The event offers two 5 km options: a Leisurely Hike and a Timed Run, inviting participants of varying paces to join th..

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..

Event overview 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 chan..

Event overview Trick or Trot 2025 is a Halloween-themed run on Saturday, October 25, 2025, at Laurel Creek Trail. The meeting area is listed as 445 Wes Graham Way, Waterloo, ON N2L 6R2. The event programme includes a costume contest at the..

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..

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..

Murphy’s Mission is a dog-and-run fundraiser held at Christie Lake Conservation Area in Dundas, Ontario. The event offers multiple ways to participate: a 5K Canicross (dog and runner tethered), a 10K Canicross (two 5K loops), a Human-Run 5K..

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 Lost Valley Trail Race is a point-to-point trail race on Saturday, November 15, 2025, finishing at Dundas Valley Conservation Area in Dundas, ON. The route follows the Iroquoia Section of the Bruce Trail and the event is..

Chill Session 2025 is a trail-running event held at Mansfield Outdoor Centre in Mulmur. Runners can choose from 10K Chill, 5K Cool, or 1K Wee Chilly for kids. The courses are mostly single-track with elevation gains around 220m for the 10K..

The Leftovers Mystery Race 2025 takes place at Dundas Valley Conservation Area on Governors Road in Dundas, Ontario. This playful trail event features mystery distances you choose on race day: a short option 6 km or less, a medium 10–15 km,..

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..