Trail Running calendar near Shelburne 2025-2026

Celebrate trails, hoodies, chili and beer at Chill Session 2025 at Mansfield Outdoor Centre. Choose a scenic 10K or 5K single track run or bring the kids for a free 1K, then relax with food, s'mores and a cold brew.

Join a half day trail running workshop at Devil's Glen and Nottawasaga Bluffs with an easy 5k social run, coach led tips on winter gear and training, and a take home plan. Enjoy a hearty lunch and support local conservation.

Hit snowy trails at the Golden Spike Trail Race around scenic Crawford Lake in Milton, Ontario on December 6, 2025. Choose 5K, 10K, or 21K and support STAC Hamilton youth programs while enjoying winter forest views and warm aid stations.

Join the Dion Mighty Chickadee Snowshoe Race on January 17 at Cold Creek Conservation Area for a scenic 6.5 km through forest and meadows with a few long climbs. Limited to 60 racers, this series stop wraps up with chili, awards and prize d..

Run the Caledon Crusher on April 11, 2026 through the scenic, rugged Caledon Hills Bruce Trail with options from 25k to a 72k End to End challenge. Enjoy onsite food, a race shirt and finisher medal while supporting the Bruce Trail.

Take on Pick Your Poison, an annual April trail ultra around Horseshoe Heights near Barrie. Choose 12.5k, 25k or 50k loops, enjoy aid stations and boxed meals, and support mental health awareness.

Join the 5 Peaks Trail Running Series at Kelso Conservation Area in Milton Ontario on May 2, 2026. Distances from a 1 km kids run to a 21 km grit course mean every runner can enjoy scenic trails and friendly race vibes.

Join Tails on Trails on May 30, 2026 at Bechtel Park in Waterloo for a family friendly trail run raising funds for the Humane Society of Kitchener Waterloo and Stratford Perth. Choose 5 km, 2.5 km or a Pup Run and bring your dog to join the..

Run scenic single track in Dufferin County Forest at The Great Mansfield Outdoors on May 30, 2026. Distances range from 5K up to a new 100 km solo or relay, with challenging roots and climbs and a finish at Mansfield Outdoor Centre.

Summit 700 invites trail runners to tackle technical single track and a 700 ft ascent of the Niagara Escarpment at Blue Mountain, with distances from a kids run to a new point to point 50 km ultra. Enjoy BBQ, patio music and awards.

Take on ENDURrun Prelim, a six day, six stage 60 km challenge across Waterloo and Cambridge, featuring trails, track heats and a final half marathon. Spots limited to 75; entries include a technical T shirt and finisher medal, with aid stat..

Run the Falling Water Trail Marathon or Half in Eugenia on Aug 8 and 9, 2026 on the rugged Bruce Trail. Limited to 100, this hilly single track race offers a two day option for two medals and benefits the trail club.

Take on the ENDURrun Sport 80 KM, an 8 day, 8 stage, 80 km adventure through Waterloo Region’s roads, trails, hills and track. Limited to 75 runners, this multi terrain challenge includes a technical shirt and a finisher medal.

Tackle rugged Bruce Trail terrain at Devil's Glen on scenic courses from 16 to 66 km, featuring steep climbs, a keyhole crawl and riverside sections. Entries support the Blue Mountains Bruce Trail Club and include a race kit and finisher me..

Join the 13th Kitchener Kids with Cancer on Sept 19 at Kiwanis Park for scenic trail 5 km and 10 km races that benefit pediatric cancer care. Family friendly with a free kids 200 m, medals for finishers, music and food trucks after the race..

Test your climbing legs at the Creemore Vertical Challenge in October, with distances from 14K to 80K over scenic gravel roads and trails. Expect big climbs, helpful aid stations, and a festive small town finish.

Run scenic, mostly fast trails at Hilton Falls with 10 km, 25 km and 50 km distances to suit every trail runner. Enjoy a few technical sections, a waterfall pin, on course s'mores, La Sportiva shoe demos and finisher swag.