Ellendale’s Railroad Square was a major rail junction and center of economic activity in Sussex County. The first section of the Junction and Breakwater Railroad, from Harrington to Milford, was completed in 1859. In March 1860, the company’s survey team, with T.F. Tilghman as chief engineer, worked south from Milford to Georgetown through forest and farmland along a route that would parallel the Federalist-era Old State Road. Construction was delayed by the Civil War and did not begin until 1867. By 1869, the line was completed through Ellendale and Georgetown to Lewes, and in 1878 it was extended to Rehoboth. The 44-mile line from Harrington to Rehoboth had 14 stations and regular passenger, mail, and freight service. Through its junctions, the J. and B. formed part of the first rail network serving Delaware, Maryland, and Virginia. In the 1890s, the Queen Anne’s Railroad was built from Queenstown on Chesapeake Bay through Ellendale to Milton and Lewes on Delaware Bay, with connections to steamboats crossing the Chesapeake to Baltimore and the Delaware to Cape May. Around the square and the rail siding to the north stood a watch box, pump house, water tower, two stations, stores, a cannery, the Ellendale Excelsior Company, and the R. J. Clendaniel Sawmill. In 1916, the DuPont Boulevard, now U.S. 113, was built a mile to the west, and as roads improved and their use increased, the railroad’s golden days ended.