In 1610, as a young man of 17, Thomas Willoughby the immigrant left Rochester, Kent, England for Virginia. His age at the time of his migration suggests that he might have been a younger son in search of the advancement that the accident of birth had denied him. But whether or not he was entitled to be called a gentleman, as he was styling himself by the 1620s, is uncertain.
Willoughby's early years in the New World are clouded by a dearth of evidence. He may have done some soldiering prior to his coming or soon thereafter, for he was listed in the muster of 1624/25 as "Ensigne Thomas Willoby." By the 1620s, though, Willoughby clearly had begun to acquire land and political offices. Although his name does not appear in the land patent records until 1628, he had already sued out patents to three hundred acres of land as early as 1626. By the time he died, Willoughby had amassed over 3,600 acres of land by patent.
His military experiences probably account for his gradual insinuation into the colony's political life. In 1627 Governor George Yeardley and the Council of State appointed him to command a militia force sent to attack hostile Indians. There after, Willoughby served as a judge on one of the monthly courts that preceded the county court system, and he sat in the House of Burgesses.
After the General Assembly erected the county courts, he became one of the first justices of the peace in Lower Norfolk County, following its formation in 1637. By the 1640s he had been elevated to a seat on the Council of State, a post he apparently occupied until Interregnum.
In addition to these public duties, Willoughby performed other community services. For his neighbors he was one of the chief creditors in the county. As such, his name regularly appears in court records as a suitor in debt actions.
Since he also engaged in a wide range of commercial activities and even made frequent trips to London, it may be surmised that he was also a contact for city merchants as well. On more than one occasion, Willoughby was asked by county officials to do such tasks as buy law books for the court of recruit a minister from England.
Thomas Willoughby died in England sometime before August 1658. He left two daughters and a son, but since he died intestate, there is no record of how his property was distributed among his heirs.
The Old Dominion in the Seventeenth Century, Warren M. Billings, 1975
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Thomas Willoughby was from Rochester, Kent, England. He came to America in 1610 aboard The Prosperorous. He was among the first settlers in that area.
July 4, 1627, Ensigne Thomas Willoughby was ordered to command an attack on the Indians.
James City Court: "At this court was thought fit that we should draw out parties from all our plantations and go upon the Indians and cut down their corn, and further that we should set upon them all in one day, vizt. the first day of August next:
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For the Chesapeakes, Ensigne Willoby
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November 17, 1628, Ensigne Thomas Willoughby of Elizabeth City was awarded a land patent of 50 acres.
In 1628/29 Thomas Willoughby was assigned as a monthly court judge in Elizabeth City.
In 1629/30 Thomas Willoughby, William Kemp, and Thomas Hayrick were Burgesses for the Assembly, representing the Upper Part of Elizabeth City.
In 1631/32 Thomas Willoughby was a Burgesse for the Assembly, representing Waters Creek and the upper parrish of Elizabeth City.
In 1639 he was Justice of the Peace, and in 1640 he was a Member of the Council of State.
Captain Thomas Willoughby was granted 2,900 acres of land for the transportation of 28 people to Virginia.
In March, 1645- 46, the assembly ordered Capt. Edward Hill and Capt. Thomas Willoughby to go Maryland and demand the return of certain Virginians who had remained there without permission. While in Maryland, Hill was chosen governor by the insurrectionist party and held office for several months.