Trail Running calendar near Bolton 2025-2026

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.

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..

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.

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..

Join the inaugural Oakville Remembrance Trail Run on Nov 9, 2025 for an 11 km route in Lions Valley to honour veterans, service members and first responders. Proceeds support Wounded Warriors Canada; please bring a reusable water bottle.

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..

Get cozy at Chill Session on November 29 in Mulmur with scenic single track trail runs for all levels and a warm hoodie for entrants. Celebrate afterward with chili, beer and s'mores while supporting local food banks.

Run the Leftovers Mystery Race in Hamilton, a playful event where you stop at checkpoints to cut mystery images with blunt scissors before moving on. Free entry with a suggested $20 charity donation and distances revealed on race day.

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..

On April 11, 2026 the Caledon Crusher at Mono Centre is a scenic but savage trail across the Caledon Hills with 25k, 50k and 72k options on technical singletrack and big climbs. Ideal for runners craving a tough, beautiful challenge.

Event overview The Foxtail Rail Trail Race takes place on April 18, 2026 at the Dundas Valley Conservation Area, Governors Road, Dundas, ON, Canada. The event is sanctioned by Athletics Ontario. Distances offered: 5 km 10 km 25 km 50 km R..

Pick Your Poison is an April trail ultra near Barrie offering 12.5k, 25k or 50k on a rugged 12.5k loop through forested climbs and spring conditions. Enjoy stocked aid stations, boxed post race food and a fun community vibe.

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

Experience historic trails in Dundas Valley at the Sulphur Springs Trail Race on May 23 and 24, 2026, with a challenging 20K loop of rolling hills and steep climbs. Distances range from 10K to 100 miles, plus team relays, and the event is a..

Event overview Tails on Trails 2026 is a community fundraising event on Sat, May 30, 2026 at Bechtel Park, Bridge Street West, Waterloo, ON, Canada. The event supports the Humane Society of Kitchener-Waterloo and Stratford Perth. The fundra..

Explore scenic trails at Crawford Lake Conservation Area with the 5 Peaks Trail Running Series on June 6, 2026. Enjoy varied terrain, community spirit and a rewarding outdoor day for runners and nature lovers alike.

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..

The ENDURrun Prelim is a six-day endurance challenge totaling 60 km in Ontario, Canada. The event begins with a prologue at Weberlyn Crescent, Conestogo, and features stages across Waterloo, Cambridge, and Wilmot (RIM Park, Riverbluffs Park..

Event overview Tally in the Valley Trail Race takes place on July 25-26, 2026 at Dundas Valley Conservation Area in Hamilton, ON, Canada. The event is sanctioned by Athletics Ontario and lists La Sportiva as an equipment partner. Race forma..