Winchester was the "end of the line" for a Pennsylvania RR branch that extended southwest from Hagerstown, MD, through Martinsburg,WV to Winchester. Most of this branch was sold to the local short-line Winchester and Western (WW) around the time when Conrail was created in 1976. A new connection with existing WW trackage was made north of downtown.
The former PRR track and sidings in Winchester were then abandoned, although several of the rail sidings are still in place. The produce warehouses formerly served by the PRR now use trucks.