Trail Running calendar near West Orange 2026-2027

The Squatchy Leftovers is a trail race in New Jersey's South Mountain Reservation, offering distances from a 5K to a 50K. It's a fundraiser for mental health charity Bigger Than The Trail. The family-friendly event uses a scenic 5K loop and..

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.

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..

An eight-hour looped run at Cooper River Park on a 3.75 mile paved circuit, featuring a personal pit area, a single start/finish aid station, cupless operations, and custom winter race swag.

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.