When a resort opened along the railroad in the late 1880s at Brandywine Springs, the passenger business flourished as people from around the region came to the park to escape the summer heat. They came to enjoy the fun house, pony rides, carousel and live entertainment. The park closed in 1923, and the passenger business ended on September 28, 1930, a victim of the Great Depression. Shortly thereafter, the Pennsylvania Railroad discontinued its connecting service to Landenberg. With trucks and automobiles gaining in popularity, the Landenberg Branch saw a sharp decrease in freight traffic, and the line was first shortened to Southwood, DE, in the early 1940s, and shortened again to Hockessin, DE, in the late 1950s.
In the mid-1960s, Historic Red Clay Valley Inc. (HRCV) was formed and began leasing the tracks from the B&O on weekends beginning in 1966, operating steam-powered tourist trains between Greenbank Station and Mt. Cuba, located mid-way between Greenbank and Hockessin. In the mid-1970s, the line's new owner, The Chessie System, determined that the line had become a financial burden and filed for abandonment of the line - fundraising by HRCV began immediately. In August of 1982, the remaining 10.2 miles of the Landenberg Branch were purchased by HRCV.