Giovanni da Verrazano, an Italian explorer in the 1500s, was the first European to visit the Chesapeake. Later came English settlers, who left England for more economic opportunities and to escape religious oppression. In 1608, Captain John Smith thought there was "no place more perfect for man's habitation" than the Chesapeake Bay. Fur trader William Claiborne thought so, too, and set up a fur trading post on Kent Island in 1631. This was the first English settlement in the upper Chesapeake.

Maryland began as a colony when King Charles I promised George Calvert, the first Lord Baltimore, a colony north of Virginia. Before he could visit the colony, George Calvert died. His son, Cecilius, became the second Lord Baltimore and the Lord Proprietor of Maryland. He named his colony "Terra Maria," or "Maryland" in honor of the king's wife Queen Henrietta Mary. Because Cecilius Calvert had to remain in England, he sent his younger brother Leonard to accompany the colonists and to be the first governor.