Trail Running calendar near Nobleton 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.

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.

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.

Run the scenic Hamilton to Brantford rail trail at the Foxtail Rail Trail Race in Dundas Valley on April 18, 2026. Choose 5, 10, 25 or 50 km on a mostly flat, fast out and back course with chip timing and medals.

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.

Sulphur Springs Trail Race weekend invites trail runners to tackle scenic single track, natural springs and steep climbs on a 20K loop. Distances range from 10K to 100 miles with team relays and WSER qualification on offer.

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.

Explore rolling singletrack and technical forest trails at The Whole Enchilada in Uxbridge, Ontario, with distances from a 1 km kids fun run to a challenging 50 km. Enjoy scenic routes, on site aid stations, and a community minded vibe.

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..

Tally in the Valley is a looped trail running festival through the scenic Dundas Valley Conservation Area, with options from a single 7 km loop to a 100 mile epic plus 6, 12 and 24 hour timed formats. Finishers earn custom medals and a belt..

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 Sticks n' Stones at Christie Lake for rolling dirt loops around the lake with distances from 5k to a 53k solo or team relay. Enjoy La Sportiva demos, aid stations and medals while supporting Oceana Canada.

Run scenic 7K trail loops at Long Sault Conservation Area with options from a kids 2K fun run to a 6 hour loop challenge. Proceeds from hoodie sales support CLOCA and sponsors include Running Room and MEC.

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.

Choose 10 km or 25 km on the Bruce Trail for scenic single track and rocky views along the Niagara Escarpment. Enjoy aid stations, shoe demos and a lively finish at Dundas Valley Conservation Area.