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1500-1600: Early Carolina Expeditions and Settlements
 

1521 – (June 24) First recorded Spanish expedition reaches the Carolina coast, probably near Winyah Bay.

1524 – First French ship scouts the Carolina coast.

1526 – (August) First Spanish attempt at a settlement, San Miguel de Gualdape, probably near Winyah Bay. Colony fails within a year, and only 150 of 500 settlers live to return home.

1540 – Hernando DeSoto may have reached Carolina Lowcountry on a trek north from Florida.

1562 – First French attempt at a settlement made by Jean Ribaut on Parris Island. Built a fort named Charlesfort. Settlement fails within a year. Similar French attempts to settle in Florida bring about bloody Spanish massacre and equally bloody French reprisal.

1565 – Founding of St. Augustine.

1566 – Spain decides to build coastal forts to discourage French settlements. First of these, Fort San Felipe (later rebuilt as Fort San Marco), is built near the ruins of Charlesfort.

1585 – First attempted British settlement on Roanoke Island founded by Sir Walter Raleigh. It is destroyed by Native Americans and survivors are rescued by Sir Francis Drake.

1587 – Second British attempt on Roanoke Island, also funded by Raleigh, fails within three years as all settlers disappear, becoming known as "The Lost Colony."

1587 – Spanish withdraw from San Marco after Sir Francis Drake burns St. Augustine.