Trail Running calendar near Milton 2025-2026

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.

Join Murphy’s Mission on 8 November 2025 at Christie Lake for a scenic 5 km loop trail event raising funds for Hamilton Animal Services. Run or walk with your dog, try canicross teams and enjoy a friendly outdoor day supporting shelter anim..

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 famili..

Run the scenic Iroquoia section of the Bruce Trail in Dundas, Ontario, with 10 km or 25 km options. Limited to 150 runners, this point to point race passes waterfalls and escarpment views and includes aid stations for a friendly trail day.

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.

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.

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.

Conquer The Canuck is a scenic loop trail race at Shades Mills in Cambridge on May 9, offering distances from 12.5 km to 50 km plus 12 hour solo and team relay options. Run the loops and support KidsAbility.

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..

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.

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.

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..

Hit the trails at Albion Hills on July 18, 2026 with the 5 Peaks Trail Running Series. Scenic, challenging and fun, this 5 Peaks Ontario Series stop welcomes runners looking for a memorable outdoor race.

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.