The person who did the most to open the southern part of North America to English settlement was somewhat of a mysterious person. Historians are not certain where Henry Woodward was born; the best likelihood is the island of Barbados. His background before he came to the colonies is also obscure, although he appears to have had talent for learning new languages.
Woodward first appeared in North America in 1664, when he accompanied Robert Sandford to the coast of Carolina. Sandford represented the interests of the lord proprietors who intended to colonize the region. Woodward remained after Sandford left, intending to learn the local Native American language. However, he was captured by a Spanish raiding party and taken as a prisoner to St. Augustine, Florida.
Woodward flourished in his new environment. He learned Spanish, converted to the Catholic faith, and became the official surgeon at St. Augustine. In 1668, Woodward escaped captivity when the English buccaneer Robert Searles made an attack against St. Augustine.
Woodward spent a year with Searles, and then was shipwrecked on the island of Nevis in the Caribbean. Surviving that mishap, Woodward went to Barbados where he found passage with the fleet that was leaving for the Carolina coast. Woodward found it easy to demonstrate his usefulness to the colonists,and he became their interpreter.
In 1670, Woodward led the first English party to move inland. He located the native village of Cofitachique, a place no other European had seen since the march of Hernando de Soto (see no. 5). Woodward’s greatest contribution to the Carolina colony occurred in 1674.
He reached the warlike Westo tribe on the Savannah River and signed an alliance with them. In the agreement, Woodward and other merchants provided guns and ammunition to the Westo, who then attacked and destroyed Spanish missions along the coast of what is now Georgia.
Woodward went to England in 1682. He obtained a commission to explore even further, and in 1685 he led a dozen Charles Town merchants to the towns of the Lower Creek Indians on the middle Chattahoochee River. Woodward returned to Charles Town followed by 150 Native Americans bringing pelts to trade.
Remarkably versatile and diplomatic, he managed to penetrate at least four worlds: the Spanish and English colonists, the buccaneers of the West Indies, the aristocratic lord proprietors, and the Indians of the Southeast. He almost single-handedly created the trade routes that were Carolina’s only source of revenue in the early years of the colony.