Henry Woodward (c. 1646 – c. 1690), often referred to as Dr. Henry Woodward, was the first British colonist of colonial South Carolina. He was instrumental in establishing relationships with many Native American Indians in the American southeast. He was a pioneer in initiating trade, primarily in deerskins and slaves, with many Indian towns and tribes.
Not much is known about Henry Woodward's early life. He is thought to have been born in Barbados. His ancestry may have been Scottish. His father was William Woodward and his mother was Esther Martin.
In 1666, Henry Woodward accompanied Captain Robert Sandford's exploration of the South Carolina coast. Woodward volunteered to remain in the Port Royal Sound vicinity and live among the Cusabo Indians, to establish relations and learn their language. For this he was granted, temporarily, "formall possession of the whole Country to hold as Tennant att Will" by the Lords Proprietors.
In 1667 Woodward was captured by the Spanish of Spanish Florida, taken to St. Augustine, Florida and held captive for about a year. As a prisoner he was well-treated. He professed Catholicism and was made official surgeon. During this time he learned about the thriving Spanish-Indian trading system. This experience helped him in rapidly establishing an English trading system after he regained his freedom.
Woodward escaped in 1668, after the English buccaneer and privateer Robert Searle raided St. Augustine. For about two years Woodward served as surgeon on privateer vessels in the Caribbean before being shipwrecked on Nevis in August 1669. He then took passage on the Carolina fleet of 1669-1670, which established Charleston, South Carolina. Henry Woodward became an interpreter and Indian agent for the fledgling colony. Starting in 1670, Woodward began taking a series of expeditions into the interior, making contact with various Indian groups. While a few Spanish expeditions had explored the interior of the American southeast in the sixteenth century, Woodward was the first English colonist to do so. Notably, Woodward was the last European to visit the paramount chiefdom of Cofitachequi in 1670.