Running trails in Chester, NY
Chester has 3 trails in the directory — 1 paved, 1 boardwalk, and 1 open 24 hours. Every one post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 309 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
Goosepond Mountain State Park
4.2 ★★★★☆ 186 reviews
State park featuring over 1,500 acres of dense woods, with established trails for hiking & biking.
Heritage Trail - Chester
4.9 ★★★★★ 97 reviews
Park featuring a paved trail that's popular for walking, running, and biking.
No trails match those filters.
How to pick a trail in Chester
- Match the surface to your legs. Chester gives you a choice: 1 paved, 1 boardwalk, and 1 mixed. Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one. More paved trails →
- Loop or out-and-back? A loop finishes back at the car with no backtracking; on an out-and-back you simply turn round at half your distance.
- Check the hours before a 6am run. 1 trail in Chester is open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 3 of the 3 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 2 have trailhead parking and 1 has restrooms in Chester. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 1 with mile markers. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Chester trails by type
Running trails near Chester
Worth the short drive — the closest towns with trails in the directory.