Trail Running calendar near Milford 2026-2027

Experience a scenic trail run through wooded hillsides and fields near the Wallkill River. Choose between a 5k or 10k race on single track trails and participate in the local athletic sneaker recycling program.

Experience a premier 13.1 mile trail race through the woods of New Rochelle. This half marathon takes runners across local trails for a focused off road experience in New York.

Tackle the technical trails of Harriman State Park at the Big Bear SquaTCh South. Choose a challenging half marathon or 10K on a scenic loop with significant elevation gain. Your registration supports local trail maintenance, and the event..

This Halloween-themed run on New Jersey's legendary Clinton Road offers a spooky adventure. Participants can choose from a Zombie Crawl, a 5k, or a 10k, all featuring zombie volunteers and a festive finish line celebration.

Explore the trails at Washington Crossing Park in New Jersey. The WXT Ultra offers 50K and 25K courses featuring scenic single-track and technical sections like Rock Hopper. Event proceeds support the local park association.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

The Fall Back Into The Trails Series returns to New York's Red Wing Recreation Area. Runners can tackle a 100k, 50k, or 10k on challenging, looped courses. All finishers earn a custom medal, and the ultras are UTMB Index races.

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.

Test the reverse direction of the 5-mile loop at Jacobsburg State Park. Choose from a single loop, a 3-hour, or a 6-hour timed event on mixed trails. It's a hiker-friendly, cupless event focused on sustainability.

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.

Celebrate the tenth anniversary of this event with an 8K or 5K trail run through Unionville Vineyards. Enjoy live music and a glass of wine at the post race reception in Ringoes.

The Raven Rocks Run is a 10k trail race through the scenic and hilly terrain of Ward Pound Ridge Reservation. The event also hosts a month-long virtual 100k walking, hiking, and running challenge. It supports the local park's friends group..

Event Overview NYC Trail Mix is an ultra trail running event that benefits the Greenbelt Conservancy. The event takes place on Staten Island, New York. The course runs through more than 35 miles of trails in the area, including remote secti..

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.

Experience technical Northeast single track trails and 3000 feet of elevation at Tarrywile Park. Choose from 10K, Half Marathon, or Marathon distances featuring scenic lake views and a sustainable cupless environment.

The FEAR Trail Fest is a 5-mile trail race on the scenic Yellow Trail in New Jersey's Lewis Morris Park. With a runnable mix of rocks, roots, and climbs, it welcomes everyone from first-timers to veterans. The event focuses on sustainabilit..

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.

Experience a diverse 5K loop course at South Mountain Reservation featuring carriage trails and technical singletrack. Choose from distances ranging from a Kid's 1M to a 50K in this community focused trail event.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

The Holmdel Classic is a December trail race in New Jersey's Holmdel Park, run on a challenging 4.65-mile loop. Participants can choose from three distances, with all proceeds supporting clean water projects worldwide. An eight-hour cutoff..