Trail Running calendar near Woodland Park 2026-2027

The 4th annual Chesterfield FALL Terrain 5K at Fenton Lane Park on October 18, 2026 features a 5K run/walk and a 1 mile Fun Dash, supports local charities, offers custom race shirts and age group awards.

Trail races in Titusville NJ with 50K and 25K options that traverse Washington Crossing Park and BaldPate, featuring a technical Rock Hopper section and aid stations. Proceeds support the Washington Crossing Park Association.

A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

A trail event at Muscoot Farm on October 25, 2026 featuring a 5 mile race plus two kids courses for ages 7 to 12 and 6 and under. Packet pickup and parking are provided and participants receive Farm Bucks and kids medals.

Trail races in the Hudson Highlands near Garrison NY featuring a Half Marathon, a 5K that follows river and historic paths, and a kids costume run on the recreation center grounds.

The inaugural Barnyard Squatch 5K is a hilly trail race across The Barnyard Sanctuary's nearly 200-acre property in Blairstown, NJ, with over 500 feet of climbing and a route past rescued farm animals. All donations go to the sanctuary.

The Tri-State New York Spartan Event Weekend at Sunflower Valley Farm on Oct 31-Nov 1, 2026 offers Sprint, Super, Kids races, Hurricane Heat formats, wooded muddy terrain, creek runs, and Spartan obstacles for competitors and spectators.

Trail races at Red Wing Recreation Area in Lagrangeville, NY featuring 100k, 50k and 10k looped courses with significant elevation, on-course aid, and finisher awards.

A costumed 5K trail run and walk at Van Scott Nature Reserve on October 31, 2026 with in-person and virtual options to raise awareness for Pregnancy and Infant Loss Awareness Month. Includes a costume contest, water stations, and family act..

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

A trail 8K and 5K at Unionville Vineyards on November 8, 2026 with chip timing, live results, onsite music, post race wine, and awards. Walkers and children are welcome and the event includes water stations and post race amenities.

A timed trail event at Jacobsburg State Park on a roughly 5 mile loop of single track and gravel. The Fall Back edition runs the course in reverse and offers 5 mile, three-hour, and six-hour formats.

A trail event at Ward Pound Ridge Reservation featuring a marked 10k race and a monthlong Raven 100k November Challenge. The course includes rocky climbs, ridgeline trails and a water stop near the Fire Tower climb.

A community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

The 46th HASHATHON 6-Mile Treacherous Trail Run takes place at Cheesequake State Park on November 8, 2026, featuring a single 6-mile trail race, same-day bib and shirt pickup, post-race beer and pizza, and awards with charity proceeds.

A trail running event on Staten Island with 50 mile, 50K and half marathon loop courses through the Greenbelt, featuring staffed aid stations and support for the Greenbelt Conservancy.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

The NSRF Long Island Turkey Trail Trot 5K will take place in Bethpage on Saturday 14 November 2026. You can run 5 kilometers.