Chester
Trail Running Calendar near Chester 2026-2027
Explore the top trail runs near Chester for 2026-2027! We've gathered 43 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A USATF-NJ Open and Masters cross country championship over a 5K course at Natirar Park in Peapack Gladstone on August 30, 2026. Registration opens July 1, entry is $40 with a $5 USATF-NJ discount and no day of registration.
September 2026
Trail runs and family friendly barn activities at Masker's Barn in Berkeley Heights, combining self guided routes, games, food and an all inclusive barn party.
Multi day trail event at Horseshoe Bend Park near Frenchtown NJ with a two mile loop, multiple ultra distances, a central base camp, and hand made wood awards.
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 run at Jungle Habitat in West Milford NJ with Half Marathon plus, 10K plus and 5K plus loops on a USATF sanctioned course featuring single track and fire road.
Oct 10, 2026 in Upper Black Eddy PA offers 50 mile, 50K, marathon and half marathon races on scenic canal towpaths with aid stations, finisher medals and nearby tent camping.
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 vineyard race in Ringoes, NJ offering 5K and 8K courses, postrace live music, a food truck, wine and awards for top finishers.
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 5 miles lollipop loop trail race in Lewis Morris Park, Morristown NJ, run mostly on the Yellow Trail with roughly 600 feet of elevation gain. The event limits entries to 120 runners, uses cupless stations and hemp bibs, and offers free course pre..