In the late 1800's there were twelve passenger trains a day stopping at the Oakland train station, and hordes of vacationers flooding the town. Perhaps the busiest section of Oakland was Railroad Street, which ran parallel to the tracks between the depot and the railroad crossing. On the opposite side of the tracks from the station were two large hotels, the Oakland Hotel (Built by the B&O Railroad Company), and the Glades Hotel. a broad boardwalk ran along both sides of the tracks, with numerous businesses stretching along the depot side. Among the businesses which were known to exist from time to time along this street, between the 1870's and the 1920's were the following (starting at the depot and leading toward the crossing):
In the 1880's Mr J.M. Litzinger operated a confectionery and Music Store next to the depot, selling all kinds of musical instruments, including pianos and organs. In the 1890's this building was converted into the Schley Hotel. Inside the hotel was the Railroad Street Restaurant and R. S. Jamison's Eureka Saloon. In 1906 the Schley Hotel was purchased by Edward Frantz and renamed the Hotel Franz.
Proceeding down the tracks there was the G.W. Delawder meat market and Charles Newman's confectionery/newsstand. In the 1890's this building housed Martin's lunch room, advertising a free lunch every Saturday between 12:00 and 1:30. By 1900 is was the side of Clyde Liller's Barber Shop, and a restaurant/ice cream parlor.
Further south was Henry Felty's green grocery, John Robinson's dental office, and J. D. Taggart's confectionery. The original Hinebaugh's Restaurant was located in the Felty Building. At the point where Wilson's Creek flows under the railroad track there was a small building set on posts above the creek, containing a Barber Shop, and later a Cobbler's Shop.
Near the center of Railroad Street was the impressive "Offutt's Big Store", which could be entered both from Railroad Street and Second Street. Further south, where the stone chimney now stands, was J. J. Reynold's Caf? and Saloon, later named Oakland Saloon and Pool Hall.
Nearing the railroad crossing a pedestrian would find a drug store, known successively as Casteel's Drug Store, Myer's Drug Store and the Oakland Pharmacy (operated by Joseph Harned). Closer to the crossing was William Malette's green grocery store and F. G. Hyde's Jewelry store.
With the advent of the automobile and diminishing of the railroad passenger traffic, the businesses along the railroad were ultimately dissolved, the boardwalks were torn up, and Railroad Street faded into history.