When complete, the trail will run from Chadron to Norfolk, a length of 321 miles (517 km), making it the longest rails-to-trails conversion in the United States.

[5] Built by the Fremont, Elkhorn and Missouri Valley Railroad (a predecessor company of the Chicago & North Western Railway) in the late 1870s and early 1880s, the "Cowboy Line" was abandoned by the C&NW west of Norfolk in 1992; the section east of Norfolk was abandoned in 1982.

The following year (1993), the Rails-to-Trails Conservancy purchased the railroad's right-of-way for $6.2 million and donated it to the state of Nebraska.

[7] A short-line railroad (the Nebkota Railway) did operate on the westernmost 74 miles (119 km) of the Cowboy Trail (from Chadron to Merriman) until 2007.

Major cities on the trail include (from west to east): Trailheads are located in Valentine and Norfolk.