Trail Running calendar near Oakville 2025-2026

Kitchener Kids with Cancer is a Run Waterloo fundraiser held at Kiwanis Park in Kitchener, Ontario. In its 12th year, it offers a 5 km run/walk and a 10 km run, plus a free 200 m Kids Run for ages 7 and under. The dirt-trail course stays entirely within Kiwanis Park, with one loop for 5K and two loo..

The Wolfpack Ultra Championship takes place in Hamilton, Ontario, showcasing Conservation Halton’s rugged backcountry. The event centers on two 50K formats: a solo 50K Ultra and a 50K Team Relay (five runners of 10K each). Runners navigate technical climbs, winding forest trails and open ridges, wit..

The Rare Trail Party will take place in Cambridge on Sunday 21 September 2025.

Willibald Pasture Dash is a cross-country–style running event held at Willibald Farm Distillery & Brewery on Reidsville Road in Ayr, Ontario. The race offers a 5 km option (two 2.5 km loops) and a 10 km option (four loops) on a pasture course described as a dash through the pasture. Participants enj..

Harvest Hustle in Guelph, Ontario is a family-friendly farm event held at Strom’s Farm and Bakery (5089 Wellington Rd 32). It offers two distances: a 5K Trail Fun Run/Walk through cedar spirals, fields, and sections of a corn maze, plus a 1/2 Mile Corn Maze Walk. The course emphasizes farm terrain a..

Pace for the Donkeys is a 5k trail run held at the Donkey Sanctuary of Canada in Puslinch, Ontario. The event features a 5-kilometre trail route and a new 1-kilometre option, welcoming runners and walkers of all ages and abilities to enjoy scenic fields and trails through the sanctuary. It serves as..

Albion Ascent Trail Race in Hamilton, Ontario offers a transit-friendly, chip-timed urban trail experience through rivers, forests and waterfalls. Distances are 5K, 10K and 21K, with routes from King’s Forest paved paths to rugged Bruce Trail sections. The 21K features a persistent climb and technic..

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,..

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 (5 loops), and 53 km (10 loops) for solo runners, plus a 53..

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 around Camp Heidelberg pond, with fast, groomed trails and som..

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..

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 the day. Attendees enjoy a family-friendly atmosphere with lun..

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..

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 or 10K, and a 5K Fun Walk with or without a dog. The scenic..

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 Lost Valley Trail Race is a point-to-point trail event run by the Iroquoia Bruce Trail Club in Ontario. Runners choose between 25 km and 10 km, with starts at Cityview Park (Burlington) or Rock Chapel Conservation Area (Dundas) and a finish at Dundas Valley Conservation Area. The courses follow..

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 and 130m for the 5K, and are marked with hot-pink arrows and..

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, and a longer 16–25 km. The course is a well-marked, scenic..

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..