The Claiborne-Annapolis Ferry Company ran both passenger and automobile ferry service across the Chesapeake Bay from 1919 to 1952. The initial service was between Annapolis, Maryland, on the western shore and Claiborne, Maryland, on the eastern shore. In July 1930, a second shorter route was added between Annapolis, Maryland, and Matapeake on Kent Island, Maryland. Business increased so rapidly at that point that another ferryboat was added. In May, 1938 the Claiborne route was changed to run from Claiborne to Romancoke, Maryland, on the lower end of Kent Island, from which passengers could then connect to the Matapeake to Annapolis run. In 1943, the Annapolis United States Naval Academy absorbed the property where the ferry terminal had been, so service was switched from Annapolis to a new terminal at Sandy Point on the western shore. By May 1951, the ferries were handling 1 million vehicles and 2 million passengers annually. Ferry service stopped running in 1952 when the Chesapeake Bay Bridge was completed.
The first Claiborne-Annapolis run was June 19, 1919, with the sidewheeler Gov. Emerson C. Harrington, named for the 48th Governor of Maryland and later President of the Claiborne-Annapolis Ferry Company. As governor, Harrington had been instrumental in getting the ferry started. In 1915, the State Roads Commission had appropriated $50,000 to establish a state-owned ferry. With the beginning of World War I, planning was put on hold until 1919. At that time a group of businessmen headed by J. P. Mehaham, of St. Louis, and Frank McNamee, of Albany, and at the urging of Gov. Harrington, formed a private company named the Claiborne-Annapolis Ferry, Inc. The state funds were instead diverted toward subsidizing the new private company. The "Old Harrington", as the boat became known, made two round trips daily, crossing the Chesapeake Bay in 1 hour 20 minutes.