The railroad had its origins in the late 1800s, when the city of Prineville was bypassed by the Oregon Trunk Railroad, resulting in the city losing business to nearby towns that did have railroad service, such as Bend.
The railroad stabilized in the 1960s and 1970s with four sawmills as customers, but by the 1990s and 2000s, the railroad lost revenue when the final two mills being served shut down, leaving the COP with only inbound lumber loads for the Woodgrain Millworks facility.