The Eastern Shore Railroad began with A.J. Cassatt’s 1882 plan for a new railroad between Pokomoke, Maryland, and Cape Charles. Construction started in April 1884, and the last spike was driven on October 25, 1884. Cassatt also improved the dredging of Cape Charles harbor and developed large steel car floats that could carry eighteen freight cars, along with tugboats powerful enough to make the trip between Cape Charles and Port Norfolk in three hours. On March 12, 1885, the tug Norfolk, towing car float number one, arrived in Norfolk with twelve cars. In 1926, the railroad bought property near Little Creek and built a new rail-water terminal, completed in 1929, that shortened the ferry route by ten miles. Besides local trains, it operated two express passenger trains between Cape Charles and New York City: the Delmarva Express, a day train with a dining car and coaches, and the Cavalier, an overnight train with sleeping cars to New York and Philadelphia. The last passenger train ran on January 12, 1958. The railroad now consists of seventy miles of main track and a twenty-six mile car float operation from Cape Charles to Little Creek.
