SS Delmarva, SS Princess Anne, and the SS Pocahontas operated out of Cape Charles to Little Creek, VA, from about 1933 to 1950. The first two vessels handled the traffic from 1933 to 1941. In 1941, the SS Pocahontas was built to handle traffic increases and was added to the fleet.
During World War II, it became necessary to add more carrying space to accommodate leave schedules — military personnel heading north on Friday and returning by early Monday. So, in the off-season, the SS Delmarva and the SS Princess Anne were taken to dry dock, cut in two, and 90 feet were added to each mid-section. The SS Pocahontas, initially 300 feet long, was renovated and 75 feet were added to her mid-section.
Around 1950, as traffic continued to increase, the ferry operation was moved to Kiptopeke Beach, VA, shortening the run by 20 minutes. The continued ferry traffic increases at Kiptopeke and a strike led to the building of the present Chesapeake Bay Bridge-Tunnel.