Trail Running calendar near Shandaken 2026-2027

Experience a technical mountain trail race at Harriman State Park featuring steep climbs and rock scrambling. Choose between 10K and Half Marathon distances with stunning views of the Hudson Valley and NYC skyline.

A fast, point-to-point half marathon descending from Slingerlands to the Hudson River in Albany. The course features paved rail trails and offers amenities like live tracking, gear check, and a post-race celebration. A free shuttle bus mana..

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.

Run or walk through the scenic orchards of New Paltz at this chip timed 5k event featuring homemade donuts and fresh cider for all finishers.

Join the 10K Run for the Osprey on a scenic trail course through Lacawac Sanctuary. The event features a 10K trail run and a 5K walk, with proceeds supporting habitat conservation. Cash prizes are awarded to top finishers.

Event Overview The Squatchywaska Mountainfest is a trail running event with two distances: a 25K (noted as closer to 17 miles) and a 10-mile race. Both courses follow a lollipop format through Minnewaska State Preserve on the Shawangunk Rid..

Experience miles of rhododendron tunnels and marsh bridges in Highland Lakes. Choose from four race distances ranging from a half marathon to 100K across gravel roads and single track trails.

The Grafton 15K is a spring trail race through the technical and muddy terrain of Grafton Lakes State Park. The 9.3-mile course features 900 feet of elevation gain, starting and finishing at the park's beach.

The Leatherman's Loop is a classic 10k trail race held each spring at Ward Pound Ridge Reservation. Entry is secured via a lottery system, with no same-day registration. It's part of a series of trail events including Run the Farm and Raven..

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

Join the Your Story Matters Falcon 5K in Oak Ridge for a scenic trail run or a vibrant Youth Color Run. Support mental health awareness while enjoying a day of community activities and local giveaways.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Rock The Ridge is a 50-mile endurance challenge set in the scenic Shawangunk Mountains of the Mohonk Preserve. The event also features a trail marathon and relay options, all while raising funds to support the preserve's conservation and ed..

The Bear Mountain Trail Challenge will take place in Bear Mountain on Saturday 2 May 2026. You can run between 10 and 50 kilometers.

Experience one of the most technical and elevation dense trail races in the Northeast. Tackle steep climbs and rugged single track through the scenic terrain of Beacon, New York.

This community trail run on Clausland Mountain honors caregivers and supports mental health and sobriety causes. Participants take on a 3.75-mile historic course, receiving a medal in an event focused on gathering, not competition.

The Towpath Trail Run in Saint Johnsville offers a flat, paved course for a 10K and a 5K run/walk. Professional timing ensures accurate results. The event is scheduled for May 9, 2026.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..

The Steel Rail Races feature a marathon, half marathon, and 8K on the scenic Ashuwillticook Rail Trail in Adams, MA. Runners enjoy a technical shirt, finisher medal, and a post-race party with live music. The event supports the maintenance..