Trail Running calendar near Roxbury 2026-2027

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Test your skill and grit at a permanent outdoor obstacle facility in Wallkill. Explore a variety of competitive sprints and non-competitive endurance courses for both adults and children over a two-day weekend.

Test your limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

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.

Experience obstacle course racing at the historic home of the 1969 Woodstock festival. Tackle forest trails and rolling hills in upstate New York with race distances ranging from a 5K Sprint to a 10K Super.

A mountain running challenge in Roxbury, NY, featuring a tough 6.5-mile race and a shorter 5k option. Both courses traverse the ski slopes and trails of Plattekill Mountain. Awards are given for top finishers in each race.

Manitou’s Revenge is a 53-mile ultramarathon through the remote Catskill Mountains. With 15,000 feet of climbing on rocky, steep trails, the course becomes progressively more difficult. It runs from Windham to Phoenicia on the Long Path.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

An obstacle course Last Man Standing event in Binghamton on June 27–28, 2026 where athletes run roughly 3 mile loops each hour until one remains. Relay teams of 3 to 6 complete either 12 or 24 hours as a team.

The Red Wing Trail Challenge offers 60K, 30K, and 15K distances on a rugged 15K loop in Lagrangeville, NY. The course features mixed terrain and significant elevation gain on each lap. Post-race food and unique finisher awards are provided.

Notchview Ultra features a 1.9-mile groomed loop trail in Windsor, Massachusetts. The event includes multiple ultra distances from 6 to 72 hours and a 100.7-mile race. Proceeds support the Trustees of Reservations and a local humane society..

Muddy Princess Albany is a 5 km obstacle mud run for women held at Harley Rendezvous Classic Inc. Join this non competitive event focused on unity and empowerment while supporting the fight against breast cancer.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

Event Overview The Wakely Dam Ultra is a 55 km ultra marathon held in the Adirondack Park wilderness of New York State. The point-to-point course follows a remote section of the Northville Placid Trail between Piseco Lake and the Wakely Dam..

Experience a loop based trail race at the Newbsanity Adventure Center featuring creek crossings and swamps. Choose between 5K, 15K, or 50K distances with an optional rucking class for those seeking a weighted challenge.

This trail run and walk supports autism awareness, with all proceeds going to charity. Participants can enjoy a scenic 5-mile loop through the woods of the Trenton Fish and Game Club. The event includes a free kids run and is timed by the U..

Test your endurance on a 0.355-mile track loop for 8 hours at Clapp Park. Enjoy a unique bottle-drop aid station and support the AYJ Fund for children with cancer. Awards celebrate all age groups and lifetime achievements.

Explore the varied trails of Fahnestock State Park in New York with a choice of 50K, 25K, or 5.5-mile races. The event includes course support, a post-race meal, and supports park conservation through its non-profit organizer.

Experience a rolling cross country run through the forests and meadows of the Landis Arboretum. This sanctioned 5K race offers views of the Schoharie Valley and access to scenic trails and gardens.

Experience the beauty of the Catskill Mountains at this zero carbon event featuring a 25K trail run and an 8K ski slope course. Both distances are open to runners and hikers looking for significant elevation gain and mountain views.