Trail Running calendar near Roxbury 2026-2027

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

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..

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..

The Wawayanda Trail Fest offers four distances on a scenic 26+ mile loop in Wawayanda State Park. The course features rhododendron tunnels, marsh bridges, and varied terrain. Crew access and camping are available at the central event site.

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 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.

Tackle the steep, technical trails of Breakneck Ridge near Beacon, NY. The course features significant elevation, panoramic vistas, and historic paths. Choose from a 42K or 21K distance on this challenging route.

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..

Hit the trails at Pittsfield State Park for the Tails & Trails State Forest Run. Choose from 50K, 25K, or 5-mile distances on a scenic loop course. The event supports local animal rescue organizations.

Celebrate a Hudson Valley tradition dating back to 1983 with the Run Like The Wind 5K in Ellenville. This scenic course runs along the Shawangunk Mountains and features a section on the newly resurfaced Rail Trail. All event proceeds suppor..

A weekend running camp in the Catskill Mountains offering guided coaching, group runs, and mental performance sessions. The schedule includes long runs with significant elevation and meals are provided. It's designed for fit trail runners l..

This 5K cross-country run and walk takes place at Peach Hill Park in Poughkeepsie, reaching the town's highest point. It's open to all ages, with proceeds supporting the park's maintenance. Awards, snacks, and a rain date are part of the co..

Event Overview The IronHike Endurance Series - Spring is a multi-day trail endurance event taking place from June 4 to 7, 2026 at Mohawk Mountain Ski Area in Cornwall, Connecticut. It features a FlexRelay format where participants can tackl..

Tackle the infamous "staircase of death" on a rugged 3.8-mile loop in New York. Choose to run solo, join a relay, or take on the flexible Fun Run over a 12-hour period. Start when you like and run as many laps as you can.