Chester
Trail Running Calendar near Chester 2026-2027
Explore the top trail runs near Chester for 2026-2027! We've gathered 46 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.
October 2026
Test your limits on a flat one mile loop at the Sussex County Fairgrounds. Choose from 6 to 72 hour timed races or certified marathon and 50K distances with full kitchen and shower access.
A community 5K and 2 Mile Walk at Garrett Mountain on October 11, 2026, with virtual and Tot Trot options; proceeds benefit the Fred Torres Memorial Scholarship Fund supporting Clifton High School athletes.
Trail loops at Jungle Habitat in West Milford, NJ, offering Half Marathon+, 10K+, and 5K+ courses with marked single track, cupless aid stations, and RideWithGPS maps.
Flat multi-distance runs along the Delaware River towpath in Bucks County offering half, marathon, 50K and 50 mile options with aid stations and tent camping at Tinicum Park.
A community 5K at Duke Island Park on October 10, 2026, run on a flat, paved trail alongside the Raritan River. Proceeds support Family & Community Services of Somerset County, which provides mental health and addiction services.
Loop-based races at Livingston Memorial Oval include timed runs, a marathon, a half marathon, and a Last Person Standing event on 0.44-mile laps.
Community 5K at Garret Mountain in Woodland Park supporting Autism awareness, with vendors, free gifts, $25 registration, and medals for special needs children.
A hilly 5K trail race on 10/25/2026 at The Barnyard Sanctuary in New Jersey that passes pastures and rescued farm animal enclosures with proceeds to the sanctuary.
November 2026
A community 5K at Smithfield Beach on the McDade Recreational Trail with post race food trucks, local vendors, music, and a family friendly gathering.
Run a scenic 5K or 8K trail course through Unionville Vineyards followed by a post race celebration featuring live music and a glass of wine.
A community 5K and 1 Mile walk at Central Park of Morris County on November 8, 2026, with in-person and virtual options supporting local housing services.
10K and 5K trail runs at Hillside Park in Andover NJ to benefit a free digital mammography program, with awards, participant shirts and on-site refreshments.
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.
A 5K trail run at Sayreville Sports Complex on November 15, 2026 supporting Stars & Stripes Veterans Center with tiered registration, participant dog tags, shirts, and awards.