Trail Running calendar near Islip 2026-2027

Hit the trails at South Mountain Reservation for this winter running event. Choose from 5K, 10K, or half marathon distances on a looped course mixing fire roads and single track. Registration is flexible, with options for advance sign-up or..

Experience a seasonal 5K trail run or walk through the scenic paths of Bethpage State Park. This family event features local refreshments and a welcoming atmosphere for participants of all abilities.

The Tarrywile Half Marathon challenges runners on technical, hilly trails in Connecticut's Tarrywile Park. With three distances available, the cupless event emphasizes trail respect and community. All finishers earn a unique medal.

Run a storybook-themed half marathon on the trails of Roosevelt Forest in Connecticut. The course is an eight-loop journey through the woods, and costumes are encouraged. A book drive is also part of the event, supporting local children.

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..

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

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.

Enjoy a post holiday run or walk through the scenic trails of Bethpage State Park. Participants earn themed swag and enjoy refreshments from local partners at this festive 5K event.

Rob's Trail Run Edition stages 5K trail runs for adults and for high school or youth runners at Stillwell Woods Preserve in Woodbury, NY. The event supports The Center for Developmental Disabilities and is produced by RaceAwesome.

Experience a unique 5K trail run at Belmont Lake State Park where the focus is on luck rather than speed. Enjoy a chance to win cash prizes and refreshments at the finish line during this late November event.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

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..

Run through Roosevelt Forest on a festive 5k trail course in Stratford. All finishers receive a custom medallion, and top runners earn awards. Holiday costumes are welcome for this charitable event.

Join this unique mystery trail run in Edison featuring five mile and two mile options through wooded terrain. Enjoy a non competitive atmosphere with a secret start location and a post run social gathering for participants over 21.