Harry Richmond Hippler (1875-1958) was a pharmacist in Philadelphia, Pennsylvania and an avid amateur photographer. He graduated Philadelphia College of Pharmacy in 1896 and married Anna Mae Fleming (1876-?) in 1897.

The Pennsylvania Railroad Company was the largest railroad in the United States in terms of corporate assets and traffic from the last quarter of the nineteenth century until the decline of the northeast's and midwest's dominance of manufacturing. The Pennsylvania Railroad (PRR) was chartered in 1846 to complete an all-railroad network across the state. In 1857 the Pennsylvania Railroad purchased the old Main Line system and eventually brought the entire line from Philadelphia to Pittsburgh under one management. Between 1855 and 1874, the PRR underwent rapid expansion and emerged as one of the two largest railroad systems in the region east of the Mississippi and north of the Ohio. Through stock purchase or lease, it reached Baltimore in 1861, Chicago and Indianapolis in 1869, St. Louis in 1870, Jersey City opposite New York in 1871, and Washington in 1872. The purchase of the Philadelphia, Wilmington & Baltimore Railroad in 1881 brought complete control of the important New York-Washington corridor, and in 1910, the PRR entered Manhattan through tunnels under the Hudson and East Rivers. Most of the main lines lying east and south of Harrisburg, Pennsylvania were electrified between 1915 and 1938.

In March of 1913, a disastrous flood occurred in Ohio, Indiana, Illinois, and western Pennsylvania. In general, more than three months' normal rainfall fell on the Ohio River watershed in less than three days. The area of greatest rainfall was in Central Ohio, but the entire central valley was visited by rains heavy enough to bring all the rivers quickly to a flood stage. The damage to these areas was extensive. The flood also paralyzed the Pennsylvania Railroad through the region. Tracks and bridges were washed away, and bridge superstructures and foundations were destroyed.

The New York tunnel extension was a huge project the Pennsylvania Railroad undertook between the years 1900 and 1910 in order to run its passenger trains directly into a centrally located station in New York City. Prior to that time, passengers coming in on the Pennsylvania or any of the other West Side lines had to leave the train with their baggage and take a ferryboat to a Manhattan station. As a result of this project, tunnels were built under the Hudson River to connect New Jersey and New York, allowing the traveler to be carried directly into Pennsylvania Station, the Railroad's newly completed station building. From there, the tunnels extended under the East River to Long Island.

More than other railroads, the PRR was highly dependent upon the coal and steel industries and was burdened on its eastern end with a high-density passenger service. After 1958, the former began an irreversible decline, and the latter became a source of red ink. The PRR merged with its major rival, the New York Central, in 1968 to create the Penn Central Transportation Company. The merger was ill-planned and the company declared bankruptcy in 1970. In 1971, the federal government created Amtrak to assume the most essential passenger service, and in 1976, viable portions of Penn Central and other bankrupt railroads in its territory were conveyed to Conrail, which rehabilitated them with federal funds.