Trail Running calendar near Palgrave 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.

Leftovers Mystery Race at Bayfront Park Hamilton on Dec 6 lets you choose your distance at the start. Playful checkpoints make you cut images with blunt tip scissors and earn a medal. Bring $20 for charity; event is sold out, waitlist open.

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 rugged Caledon Hills on the Caledon Crusher, a technical Bruce Trail race with sustained climbs and singletrack. Choose 25k, 50k or the epic 72k for scenic, challenging trail running.

Run scenic rail trail through Dundas Valley Conservation Area with 5, 10, 25, and 50 km options. Chip timing, finisher medals, and a charity fundraiser for Melanoma Canada make this spring race a community friendly challenge.

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 on May 2, 2026 for trail runs from a fun 1 km kids race to a challenging 21 km grit course. Scenic singletrack and options for all abilities make it a great spring outing.

Race the Seaton Scramble on May 9, 2026 in Pickering along scenic single and double track trails with creek crossings, stairs, hills and viewpoints. Distances from a 1K kids run to a double loop 50K support Lakeridge Health Foundation.

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.

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..

Experience rugged single track trails at Great Mansfield Outdoors on May 30 2026 with looped 25 km courses for distances from 5 km to epic 100 km. Scenic forest terrain, full aid stations and camping make it a perfect trail running getaway.

Run the 5 Peaks trail race at scenic Crawford Lake with distances from 1 km kids races to an 18 km challenge. Enjoy forest trails, reconstructed Indigenous longhouses and a welcoming community of spectators and volunteers.

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.

Run the Bruce Trail at Kelso Conservation Area on July 11, 2026 with 10, 25 and 50 km point to point courses for a capped field of 200. Expect varied single track, aid stations and shuttles, plus a donation to the Toronto Bruce Trail Club.

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 returns to Dundas Valley in Hamilton on July 25 and 26, with scenic 7 km loops through Carolinian forest. Choose from 7 km, 21 km, 100 miles and 6 12 and 24 hour events, with La Sportiva demos and giveaways.

Take on the Falling Water Trail Marathon or Half in Eugenia, Ontario at Beaver Valley Ski Club, on the rugged Bruce Trail with steep climbs, waterfalls and rocky single track. Limited to 100 runners per distance; bring your own cup or bottl..

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.