The first European to enter the Chesapeake Bay region was Spanish explorer Vicente Gonzalez in 1561. Following several failed settlement attempts, the Spanish left the area in 1571, never to return. In 1605, the French started a colony at Port Royal (now Annapolis). In 1607, the Jamestown settlement was established on the James River. In 1608, sailing from Jamestown, Captain John Smith was the first European to thoroughly explore and map the Chesapeake Bay. In 1634, Lord Baltimore, who had been granted the land from the Potomac River north to what is now Pennsylvania and Delaware by the King of England, established the first English colony in Maryland, known as St. Mary's City
Since those early explorations, the Chesapeake Bay has enjoyed a varied maritime history. Bay waters have been traveled by all manner of ships throughout the ages, often specifically designed or modified to sail the Chesapeake's shallow waters. Navigation in these shallow waters has been aided by a series of lighthouses. The first light house built by the United States was built in 1792 at Cape Henry, marking the entrance to the Chesapeake Bay. Bay navigation has been aided by lightships, towers, and screw piles.
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Chesapeake Bay History Links
Chesapeake Bay Boats: Information on traditional boat types unique to the Chesapeake Bay
Exploring the Chesapeake, Then and Now. Lots of good information from National Geographic.