Trail Running calendar near Glenwood 2025-2026

Take on the Buffalo Beast, a 3 mile trail race at Kissing Bridge All Seasons Resort on Nov 1, 2025, featuring technical singletrack, steep climbs and over 800 feet of elevation gain. First 50 entrants get a commemorative pint glass and top..

Run a scenic 3.25 mile loop through the vines at Schulze Vineyard & Winery in Burt, NY on November 1, 2025. Celebrate with live music, snacks and the winery open for tastings, plus awards and keepsake prizes.

Take on the Dirt Cheap Stage Race, a three day trail series at Mendon Ponds Park Nov 7 to 9, 2025. Pick one, two or all three stages from a short time trial to an 11 mile epic and enjoy post race food and finisher swag.

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..

Test your endurance on the Manchester Gateway Trail by completing as many 2.3 mile out and back laps as you can in six hours. Entry helps fund the local dog park and well behaved leashed dogs are welcome.

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.

Run or walk the Batavia Turkey Trot 5K on Thanksgiving Day and support Crossroads House. Family and stroller friendly with costume prizes, hot drinks and snacks after the race.

Join the Gratitude Run in Rush NY on November 27 and 28 to support Rochester Rotary Sunshine Camp. Family friendly 5K trail, 1 mile and kids dash with chip timed results, shirts and post race food.

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.

Tackle rugged trails and steep climbs at the 0 Degree Winter Trail Festival in Pittsford, NY, a fundraiser supporting local trail projects. Choose 5, 10 or 15 mile routes for a cold season trail challenge with grit and scenic views.

Start the season with Frozen Assets, a scenic 10k winter trail loop at Harriet Hollister Spencer State Recreation Area that often runs through snow. Carry your own water and enjoy warm cider at the finish.

Mrs. McCormick's Ice House is a winter trail race on Jan 17, 2026 featuring a scenic, roughly 4 mile loop you can repeat for longer distances. Expect snowy trails and post race pancakes, hot drinks and awards at cozy Wilson Lodge.

Run Devil's Shadow Winter Trail Races at Mendon Ponds Park on January 31 2026 with 50k 25k and 5 mile loops around the Devil's Bathtub. Hopkins Point Lodge provides a warm aid station and post race treats while Common Ground Series swag awa..

ROCovery #OMAAT 24-Hour Run/Walk Challenge The event takes place April 18–19, 2026 at Fellows Road Park in Fairport, NY (499 Fellows Rd, Fairport, NY 14450). It is a 24-hour run/walk challenge that uses a looped course. The course is a one-..

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.

Medved Madness at Mendon Ponds Park on May 3, 2026 features a challenging long trail of about 13 miles, a shorter 5 mile course, and a kids race. Expect changing courses each year, a post race barbecue, and a friendly trail running vibe.

Take on the rugged Sehgahunda Trail Marathon and relays at Letchworth State Park on May 16 with the Vale of Three Falls races on May 17. Expect technical singletrack, big climbs, handmade finisher medals and a true trail weekend.

Run the Vale of Three Falls at Letchworth State Park on May 17, 2026 with 5K, 10K or 15K routes that follow a scenic service road overlooking the Genesee River. Expect rugged terrain, big hills and post race refreshments.

The Mills Miles - May 23, 2026 The Mills Miles is a Last Runner Standing format race held at Powder Mills Park in Pittsford, NY, with Race HQ at Powder Horn Lodge. The event uses a one-mile trail loop. Each loop is a mass start with a prede..