The Olive Hill C & O Depot was constructed on the southern side of Railroad St. in 1910 and was designed in the prairie architectural style of the period. The building was divided into five sections which included two waiting rooms, a ticket office, a restroom, and a baggage room. In fact, the Chesapeake & Ohio Railroad wanting to regularly stop in Olive Hill, because of the hills surrounding the town being rich in natural resources, is what put Olive Hill on the map. The abundance of timber, iron ore, and clay caused the nation to become greatly interested in the town in the later 1800's and early decades of the 1900's.
The George Washington and the Fast-Flying Virginian were two of the passenger trains that regularly stopped in Olive Hill. However, when the decrease in demand for timber and firebrick occurred (which shut down the brickyards) the railroad decided to end all passenger traffic...with the last ticket being sold on April 20, 1971. The railroad tracks were removed by the CSX company in the mid 1980's.
Today, the Olive Hill Depot serves as a Welcome Center and as the Trail Head for Olive Hill Trail Town Inc. Information concerning businesses, restaurants, trails, attractions, and more can be obtained at the welcome center. It also holds a gift shop as well as a Tom T. Hall display, which was donated by "The Storyteller" himself (as well as displays of other Olive Hill notables and of Olive Hill history).
In June 2023, Olive Hill welcomed a new addition to its historic railroad legacy: the C&O Caboose 90712. Relocated from its previous home at the John "Hop" Brown Memorial Park, the caboose now resides beside the Depot, anchoring the Welcome Center area with renewed significance. Restoration of Caboose 90712 is scheduled to begin in November 2025, marking another exciting chapter in Olive Hill’s ongoing celebration of its railroading heritage and community pride.