The Orange Heritage Trailway is a 19.5-mile (31.4 km)[1] rail trail in Orange County, New York, that runs along the roadbed of the Erie Railroad's Main Line from Harriman, NY to nearby Middletown.

The undeveloped roadbed continues for less than a mile, past the now demolished old Harriman station until River Road where the paved trail begins, with an informal trailhead and parking lot located at the corner of River Rd.

There is a Norfolk Southern siding off the NYS&W mainline near Chester that runs along the rail trail for about 0.5 miles.

[2] In 1999, Paul Harnisch, an assistant district attorney for Orange County, was charged with murder for striking two skaters, killing one of them, while driving illegally on the trail in the Chester area.

[3] He was found not guilty for reason of insanity and remanded to the custody of a psychiatric hospital for a period of years.