Port Cape Charles is located near the mouth of the Chesapeake Bay on the western shores of southern Delmarva Peninsula on Virginia's Eastern Shore. Part of the Chesapeake Bay Waterway, Port Cape Charles is about 30 nautical miles (46 kilometers or 28 miles) northeast of the Port of Norfolk. It is also about 125 nautical miles across the Chesapeake Bay (225 kilometers or 140 miles south-southeast) from the Port of Baltimore. Established in the late 19th Century as a planned community, Port Cape Charles was home to about one thousand people in 2010.

Until 1963, Port Cape Charles was the terminal for the Little Creek-Cape Charles Ferry that carried passengers and cars between Hampton and Norfolk. Port Cape Charles is still a terminal for railway barges that move rail cars from the Bay Coast Railroad to Norfolk.

When Captain John Smith arrived in the future Port Cape Charles area in 1608, the Nanticoke people inhabited the Chesapeake Bay region and Delaware. Their original tribal name, Nantaquak, meant people of the tidewaters. After Europeans arrived, The Nanticoke were soon allied with and traded beaver pelts with the English. Several Nanticoke served Captain Smith as guides as he explored what came to be known as the Nanticoke River to the northwest of Port Cape Charles.

The Nanticoke were productive farmers with rich gardens of corn, beans, pumpkins, squash, sunflowers, and tobacco and gathered berries, nuts, bird eggs, and edible plants during season, and they enjoyed plentiful seafood. The Nanticoke lived in seasonal villages with groups of dome-shaped wigwams, and larger structures called long houses were used for council meetings and gatherings.

The Nanticoke remained neutral during the French and Indian Wars, and they allied with the British during the American Revolution. After a century of conflict, the British compensated the Nanticoke for the lands they had lost by resettling the Nanticoke at the Six Nations Reserve in Ontario, Canada. Some of the Nanticoke remained in New York at the Buffalo River. Others joined the Lenape and moved to the Indian Territory (future Oklahoma) in 1867. Many Nanticoke who remained at the Eastern Shore assimilated into white society.

Since 1881, the Nanticoke Indian Association of Millsboro, Delaware, has been a state-recognized tribe living near the Indian River. The association was chartered as a non-profit organization in 1922, and they conducted annual powwows through the middle 1930s. In 1977, they began to hold the annual powwows again, and the two-day events are attended by tribes from the East Coast and almost 30 thousand non-natives.

In 1884, the New York, Pennsylvania, and Norfolk Railroad established the Port Cape Charles at the mouth of the Chesapeake Bay on Virginia's Eastern Shore as a planned community when they dredged a new harbor. In 1890, the US Army Corps of Engineers dredged the Port Cape Charles harbor basin and entrance as well as channel through Cherrystone Inlet. The Corps also built jetties to protect the Port Cape Charles harbor.

Port Cape Charles provided a link between the railroad and tugs to railroad barges. By 1912, Port Cape Charles was handling about 2.5 million tons of freight each year. Today, it is one of the few remaining operations of its type in the United States.

The rail line between Pocomoke City and Port Cape Charles was completed in 1884. Founded by Alexander Cassatt as the New York, Philadelphia, and Norfolk Railroad, the barge Cassatt designed could carry 18 railcars. Co-founder William Scott financed the construction of the town.

Port Cape Charles has a variety of architectural styles that include gingerbread ornamentation and a few Sears Roebuck mail-order homes that appeared in the 1920s. Port Cape Charles' founders include Alexander Cassatt, brother of painter Mary Cassatt, and William Scott. Scott was a rail and coal magnate and friend of President Grover Cleveland. Cassatt and Scott built a huge truck farm beside Port Cape Charles that is today's Bay Creek development.

After he left the Eastern Shore and Port Cape Charles, Cassatt was instrumental in building Manhattan's Pennsylvania Terminal, including tunneling under the Hudson River. He did not live to see the terminal completed, and it was razed in the 1960s to make way for Madison Square Garden.

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