Thomas Willoughby II was born in Virginia in 1632. His father intended that he should be trained in a mercantile calling, for the elder Willoughby sent the boy to the Merchant Taylors' School in London when he was twelve.
The earliest evidence of Thomas II in the records of Lower Norfolk County occurs in April 1656, when he turned down an appointment to the bench, and a month later when he was fined for refusing jury duty.
His refusal of both responsibilities may have resulted from his royalist sympathies, a supposition that is borne out by his acceptance of a commission as a justice of the peace a year after Sir William Berkeley's restoration as governor in 1660.
Like his father, Willoughby held several other county posts during his tenure on the Lower Norfolk Court. A colonel in the county's militia, he also served one term as sheriff in 1666.
At the time of the Second Anglo-Dutch War he was one of the commissioners appointed to oversee the construction of a fort on the lower James River. But unlike the elder Willoughby, the son never served in the House of Burgesses or on the Council of State.
Sometime prior to 1659 young Willoughby married Sarah Thompson, daughter of a planter in Northumberland County. They had a son and a daughter who grew to adulthood. By 1672 Thomas Willoughby was dead at the age of 40.
"The Old Dominion in the Seventeenth Century"
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Legend has it that his wife awoke one morning following a terrific storm (possibly the "Harry Cane" of 1667) to see a point of land in front her home, where there had been only water the night before. The Willoughby family, it is said, were quick to apply for an addendum to the original land grant, giving them ownership of the "new" property.
Thomas was apprenticed as a merchant 1644-1647.
In 1656 he refused to be sworn as Justice of the Peace (Commissioner), and he was fined 150 pounds of tobacco for refusing jury duty.
In 1661 he served as a Commissioner, 1666 he was Sheriff, and in 1667 he was a Commissioner for Nansemonde Fort for the building of a fort there.
Thomas Willoughby II married Sarah Thompson, daughter of Richard Thompson. She and her sister Elizabeth, who married Peter Presly, inherited over 2000 acres from their father, which was assigned to their husbands.
Thomas and Elizabeth had two children, named Thomas and Elizabeth.
Thomas Willoughby 
