Running trails in Ossining, NY
Ossining has 9 trails in the directory — 1 loop that returns to the trailhead and 4 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 1,655 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.
Teatown Lake Reservation
4.8 ★★★★★ 750 reviews
1,000-acre parkland offering 15 mi. of hiking trails & an indoor/outdoor nature education center.
Kitchawan Preserve
4.7 ★★★★★ 277 reviews
Nature preserve offering trails and scenery for hiking, dog walking, and exploring old ruins.
Nelson Park
4.4 ★★★★☆ 246 reviews
Neighborhood green space for walking and sports featuring a baseball field, tennis courts and a playground.
Ryder Park
4.4 ★★★★☆ 100 reviews
Local park offering baseball fields and tennis courts. Also features a playground for kids, a basketball court and a dog run.
Gerlach Park
4.3 ★★★★☆ 71 reviews
Park offering baseball, softball, and basketball fields, plus picnic tables.
Sunny Ridge Preserve
4.4 ★★★★☆ 65 reviews
Hiking and walking trails, as well as flora and fauna, in a wooded preserve.
No trails match those filters.
How to pick a trail in Ossining
- Match the surface to your legs. 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.
- Loop or out-and-back? 1 trail here is a loop, so you finish back at the car with no backtracking — the easiest way to run a set distance without thinking about it. On an out-and-back you turn round at half your target distance, which makes any trail fit any run.
- Check the hours before a 6am run. 4 trails in Ossining are open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 9 of the 9 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 4 have trailhead parking, 3 have restrooms, and 2 have a water fountain in Ossining. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 3 that runners describe as quiet and 6 dog-friendly. 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 Ossining trails by type
Running trails near Ossining
Worth the short drive — the closest towns with trails in the directory.