Orange Heritage Trail – Monroe Ponds loop from Chester

Running trails & routes

Orange Heritage Trail – Monroe Ponds loop from Chester

Hard

3.0

(4)

runners

Orange Heritage Trail – Monroe Ponds loop from Chester

02:40

25.7km

120m

Running

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: August 19, 2026

Waypoints

Start point

Parking

Get Directions

8.30 km

Orange Heritage Trail

Highlight (Segment) • Trail

Once the location of the Erie Railroad's Main Line, this is now a paved multi-use trail that runs 19.5 miles in total.

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12.7 km

Mill Pond

Lake

12.7 km

Orange Heritage Trail

Highlight (Segment) • Trail

The Orange Heritage Trail stretches a total of 19.5 miles from Middletown to Harriman, New York. The path is entirely paved and is super popular among runners, walkers, and cyclists. …

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16.6 km

Monroe Ponds

Highlight • Lake

You can bike a road loop all the way around these ponds, or consider linking in to the nearby Orange Heritage Trail.

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16.7 km

Crane Park Pond

Highlight • Lake

Crane Park (sometimes referred to as Millpond Park) is home to a couple small ponds, a gazebo, paved walking paths, and lots of open green space. There is easy access …

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23.2 km

The Orange Heritage Trail is an almost 20-mile long rail trail that runs from Middletown to Harriman. It is paved and traffic-free. This section is used by the Long Path to take you from Monroe to Chester.

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