William Woodford was the most distinguished man in Caroline in the early days. Born in England, he had established an excellent military career in his youth. He had fought with Spotswood under Marlboro at Blenheim, and later came to Virginia upon Governor Spotswood's invitation, who made him magistrate of Essex County upon his arrival. He was one of Spotswood's "Knights of the Golden Horseshoe," and acquired large land holding in St. Mary's Parish through his marriage to Elizabeth (Smith) Battaile. He was one of the eighteen men (together with John Battaile and John Talioferro) who were appointed as magistrates to erect Caroline County.
He was the first sheriff of Caroline, appointed by Governor Gooch, and held court in his house until a prisoner, Benjamin Fletcher, escaped. Fletcher was being held for non-payment of debts to Richard Sutton. The magistrates ordered Woodford to pay Sutton in full. The House of Burgesses reversed the magistrates' decision on Woodford's appeal, and ordered the magistrates to reimburse the sheriff and build a courthouse and jail.
Later, Woodford opposed the Burgesses' ruling regarding the limitation of tobacco plants that could be planted per acre, and the forbidding of tending suckers. He lead a large delegation of planters to Williamsburg to argue for the repeal of the ruling, and stated that he was in the process of inventing a machine that would make tobacco planting and tending more efficient. Increased tobacco production was exactly what the Burgesses did not want, and the original ruling stood.
In 1742, Woodford joined with Dorothy Roy to discredit Conway's tobacco warehouse. There were two accredited tobacco warehouses in the county - Roy's and Conway's - and Dorothy Roy was determined that she would have a monopoly. Woodford accused a Conway inspector, William Allcocke, of passing tobacco (giving a passing grade to inferior tobacco) for Lawrence Battaile, his wife's son. The court found no basis for the accusation.
In addition to the lands he inherited through marriage, he received large grants from Governor Gooch, located in Lunenburg County, and extending into the colony of North Carolina.
Upon Woodford's death in 1761 or 1762, his son, William Jr., took over. William Jr. had accompanied Col. George Washington on the expedition to build Fort Necessity on the Ohio River. While the fort was being built, the French forced them to withdraw. During the French and Indian War William Jr. commanded the Caroline troops, and built Fort Mindenhall in Frederick to hold the Indians back.
Upon the death in 1762 of Benjamin Robinson, the highly regarded first county clerk of Caroline, Benjamin's son, Joseph Robinson, took over the position. The job was deemed to be too rich a political plum to allow this, and local politicians convinced Governor Faquier to 'use the office to provide sustenance for undistinguished sons of distinguished sires.' Faquier appointed Robert Armistead, son of Henry Armistead, Caroline's first county lieutenant, to the post, with Cotesby Woodford, the rather ineffectual son of William Woodford Sr., as chief deputy. John Timberlanke, a commoner with no political clout, was appointed as junior deputy to do the actual work. Young Woodford moved from Caroline three years later.
William Woodford, Jr. went on to become a military hero in the Revolution, and an even greater political power than his father.
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