Henry Fleet

Henry is thought to have come to the Virginia in 1621 with the new Governor Sir Francis Wyatt, first cousin of Deborah Scott. In 1622 the Powhatan tribe executed a widespread massacre in the Virginia Colony, killing about 330 settlers. The following year Henry Fleet accompanied Henry Spelman and several other men up the Potomac River in search of less hostile natives to make a trade deal and supply Jamestown with corn. Spelman had arrived in Jamestown as a boy in 1609 as a part of the third supply with George Yeardley, he was traded to the Indians by John Smith soon after his arrival to learn the native language. Spelman formed good relations with many in Powhatan's tribe and become a successful interpreter and trader. For some reason the 1623 expedition failed and warriors from the Anacostan tribe attacked the ship and killed every member of the trading party except Henry Fleet.

Henry lived among the natives for about five years before a deal was negotiated and a ransom paid for his release. During this time he learned the tribe's language and culture. When freed Henry briefly returned to England where he took employment with Colbery and Company and part of the fur trade on Kent Island, Maryland. Henry was made master of ship and returned to the colonies to use his knowledge of the natives as a trader. He documented some of this period in a journal. He acted as a guide to Leonard Calvert and his settlers in 1634 to help form St. Mary's, Maryland. For his work in Maryland Henry was given 4,000 acres but he never seated it. In 1629 Henry recived a patent for 100 acres in Northampton County on the Eastern Shore, again he never property claimed the land. By 1638 his brothers had joined him in Maryland and they all four sat on the state Assembly that year.

After another Indian uprising in 1644 Henry was able to use his experience with the natives to negotiate peace with Opencancanough and ultimately opened up the Northern Neck of Virginia to English settlement. By the time of English Civil War Henry had left his interests in Maryland with Calvert and and aligned himself with Virginia. Henry had held land in Virginia as early as 1629, when his name was mentioned in a patent to Thomas Graves. Eventually he patented 13,197 acres in the Northern Neck as he continued to be prosperous in the fur trade. In 1645 the Virginia Legislature authorized Captain Fleet as, "a fit person acquainted with the language of the Indians, and accustomed to intercourse with them, to trade with the Rappahannocks, or any Indians, not in amity with Openchancanough."

In 1650 Henry patented 1,750 acres in what was then Northumberland but is now known as Fleet's Island in Lancaster County. Fleet's Bay also bears his name. Henry served as a Burgess for Lancaster County in 1652, a justice from 1653 until his death, and was recorded as lieutenant colonel of the militia in 1657.

Henry married late in his life to the widow Sarah Burden who had a daughter named Mary Burden. They had one son, Henry Fleet born about 1658. Henry Fleet, Sr. died before May 8th, 1661 when county court documents mention the widow Sarah Fleet. Henry died without a will. He is thought to be buried on Fleet's Island, the will of Henry Fleet, III directed a brick wall be built around the family burial plot. Sarah remarried to John Walker and had two more daughters. Sarah married a fourth time in 1672 to John Stone before her death in 1679. She left a will in Old Rappahannock County and mentioned Henry Fleet, Jr.