Woodward volunteered to remain in the Port Royal Sound vicinity and live among the Cusabo Indians, to establish relations and learn their language.
This experience helped him in rapidly establishing a trading system with local Native American after he regained his freedom.
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 Anglo-American colonist to do so.
These Shawnee had probably migrated to the Apalachicola River region in the 1640s in order to trade with the Spanish and perhaps to escape the Iroquois wars in the north.
[5] Later the Apalachicola Shawnee migrated to the Savannah River area, approached Henry Woodward privately and established a relationship that eventually doomed the Westo.
In 1682, Woodward got shot in the head but still manage to travel to England, where he not only obtained a pardon, but an official position as Indian agent for the Lords Proprietors.
[6] A group of Scots founded a settlement, called Stuarts Town, in the Port Royal Sound area of South Carolina in 1684.
In 1685, Henry Woodward found himself arrested in Stuarts Town while passing through the area on mission to the "proto-Creeks" of the Chattahoochee River.
His arrest was apparently due to the desire of Lord Cardross of Stuarts Town to control trade with the Creek.
The Yamasee, backed by the Stuarts Town Scots, conducted a series of devastating raids on the Spanish mission province of Guale and then proceeded to invade the province of Timucua in Florida, bringing back many Indian slaves to sell to the Scots of Stuarts Town.
Woodward is generally credited with introduction of viable rice crops to the colonies stemming from his time in Charles Town in 1685.
Pirate trader John Thurber returned from a trip to Madagascar with a bag of seed rise which he gave as a gift to Woodward, whose experiments showed that the marshy soil was ideal for rice cultivation.
Woodward was involved in this initial stage of English-Chickasaw relations, but he died before the first adventurous traders traveled to Chickasaw territory in the early 1690s.