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Orange Heritage Trail – Monroe Ponds loop from Chester

Routes

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: May 8, 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.

Tip by

12.7 km

Mill Pond

Lake

12.7 km

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. There are a bunch of different trailheads and parking areas, so you can start your walk from a number of spots and make it as long as you want.

Tip by

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.

Tip by

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 over to the Orange Heritage Trail from the park and a couple different parking areas that you can utilize.

Tip by

23.2 km

Orange Heritage Trail

Highlight (Segment) • Trail

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.

Tip by

25.7 km

End point

Parking

Way Types & Surfaces

Way Types

25.6 km

< 100 m

Surfaces

24.1 km

802 m

565 m

325 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (190 m)

Lowest point (130 m)

Weather

Monday 18 May

34°C

16°C

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Orange Heritage Trail – Monroe Ponds loop from Chester

Orange Heritage Trail

Orange Heritage Trail

Monroe Ponds

Crane Park Pond

Orange Heritage Trail

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