Running trails in Oyster Bay, NY
Oyster Bay has 8 trails in the directory — 2 on crushed gravel or dirt, 2 loops that return to the trailhead, and 2 open 24 hours. 5 of them post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 6,668 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.
Planting Fields Arboretum State Historic Park
4.8 ★★★★★ 2,844 reviews
Greenhouses, gardens & summer concerts on a 409-acre estate with an original Tudor Revival mansion.
Theodore Roosevelt Memorial Park
4.6 ★★★★★ 1,885 reviews
Bayside park with athletic fields & courts, playgrounds, boat ramps & a beach on Oyster Bay Harbor.
Sagamore Hill National Historic Site
4.7 ★★★★★ 1,743 reviews
Former home of Theodore Roosevelt with museum, nature trails, beach & visitor center on 83 acres.
Nature Trail
4.8 ★★★★★ 86 reviews
Wildlife refuge featuring a hiking trail leading to a beach.
Hope Goddard Iselin Preserve
4.8 ★★★★★ 43 reviews
Park, preserve, and tourist attraction known for its trails through woods, some with pine trees and meadows.
Tiffany Creek Preserve
4.3 ★★★★☆ 47 reviews
Shady park featuring several trails, ranging from flat to hilly, for hiking and snowshoeing.
Red Cote Preserve
4.4 ★★★★☆ 18 reviews
Massapequa Preserve
5 ★★★★★ 2 reviews
No trails match those filters.
How to pick a trail in Oyster Bay
- Match the surface to your legs. Oyster Bay gives you a choice: 2 natural surface 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 natural surface trails →
- Loop or out-and-back? 2 trails here are loops, 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. 2 trails in Oyster Bay are open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 5 of the 8 listings carry posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 5 have trailhead parking and 3 have restrooms in Oyster Bay. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 6 that runners describe as quiet, 3 dog-friendly, and 2 smooth and wide enough for a stroller or a wheelchair. 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 Oyster Bay trails by type
Running trails near Oyster Bay
Worth the short drive — the closest towns with trails in the directory.