While it was possible to connect to the Chesapeake Beach Railway from Baltimore by train and later automobile, most visitors from that city took advantage of regular steamboat lines that sailed down the Chesapeake Bay. There were several lesser known steamers that docked at the beach throughout the years, however it was these regulars that were noted and recorded more often. When the resort opened in 1900, the J.S. Warden, a side-wheeler built in 1863, brought an estimated one-thousand people to the opening of Chesapeake Beach. It was retired in 1912, replaced by the popular Dreamland, another side-wheeler built in 1878 that held up to 2,500 passengers. The Dreamland sailed to and from the beach from 1909-1925. The Wilson Line was the next fleet to serve the beach in the 1930s and 1940s. The steamers from this fleet were the City of Wilmington, State of Delaware, Dixie, and Bay Belle. Steamboat service ended in 1942 due to gas rationing during World War II.
Because of the shallow water at Chesapeake Beach, a pier for the safe docking of steamboats had to stretch almost a mile out into the bay. In the earliest days of the resort, the so-called Long Pier was situated at the northern end of the boardwalk. In 1914, it was rebuilt on the southern end. After a hurricane in 1933, the Long Pier was reconstructed in the same location except that the landward end curved ashore slightly further north. To alleviate the long, hot hike from the steamboat to the boardwalk area, in 1930, a miniature train was installed on the Long Pier to carry passengers to and from the boat.