Drysdale was born in County Kilkenny, Ireland, either in 1672 or in 1673, and was the son of an Anglican clergyman, Hugh Drysdale, and his second wife, Elizabeth Fox Drysdale. He matriculated at Trinity College, Dublin, on May 8, 1688, at age sixteen and entered Queen’s College, University of Oxford, in February 1692. With the appellation gentleman, Drysdale was commissioned an ensign in 1694 and embarked on a career in the army. He served in Ireland from 1701 to 1703 and probably saw action in Portugal early in the War of the Spanish Succession. He likely participated in the major campaigns of that war and from 1709 to 1713 was a major and second in command of a marine regiment under a nephew of the duke of Marlborough. On April 20, 1712, in London, Drysdale married Hester Mann. An assertion made late in the nineteenth century that they had a daughter who married into the Herndon family of Virginia has not been documented, and inasmuch as neither Drysdale nor his widow mentioned children in their wills, it is unlikely that they had any who survived.
Drysdale undoubtedly knew the leading military men of his time, including George Hamilton, first earl of Orkney, one of Marlborough’s ablest generals, who was appointed governor of Virginia in 1710 and became a member of the official household of George I in 1714. Drysdale was therefore a logical choice to be appointed lieutenant governor of Virginia on April 3, 1722, after the king’s ministers decided to replace Alexander Spotswood with another experienced officer as deputy to the absentee Orkney. Drysdale took the oaths of office in Williamsburg on September 27, 1722, and with his wife took up residence in the governor’s palace.
Council member(ca. 1664–1732) praised Drysdale’s “Mild Temperate & Courteous disposition” in 1723 and stated that “the Generallity of the Country think themselves very happy in him.” (1678–1749), whom Drysdale recommended as a person qualified to sit on the governor’s Council, wrote, “God Almighty can make such another man; but I sincerely beleive he never made a better” [sic]. Drysdale was fortunate to arrive in the colony when the population was rapidly expanding, new land was being opened to settlement in the West, and war was not a threat. Few serious controversies disturbed the political peace, and, in spite of low tobacco prices that resulted from overproduction, his administration was comparatively uneventful.
Drysdale cooperated in ecclesiastical matters with, Virginia representative of the bishop of London and a member of the Council, and joined him in urging increased support for the College of William and Mary. When Drysdale summoned the General Assembly in May 1723, he proposed reforms to the militia laws and the laws governing crimes committed by slaves, which helped calm fears following rumors of an insurrection. He signed a bill to tax imported alcohol and slaves in order to augment the colony’s revenue, but slave traders successfully lobbied the Crown to disallow it. Drysdale also approved a bill that passed in 1723 to reduce tobacco production with a hope of raising its price. Taking the side of the planters earned him their respect and contributed to the spirit of harmony that prevailed during most of his administration. Drysdale was not successful, though, in reforming land office practices that had allowed Spotswood to engross large quantities of land, probably because he died before the issue was settled. Spotswood mounted a spirited defense of his earlier practices, and other Virginia planters may have feared that if Drysdale succeeded it would dash their own expectations of acquiring and selling or renting valuable western land.
Drysdale summoned the second assembly of his administration for the dispatch of largely routine business in May 1726. By then he had been in poor health for two years and had requested permission to return temporarily to England, but early in the summer of 1726 he postponed his departure when his health gave signs of improving. Having taken a sudden turn for the worse, Hugh Drysdale died in Williamsburg on July 22, 1726. He was buried in the yard of Bruton Parish Church in Williamsburg, although it is possible that his widow later had his remains transferred to a tomb she purchased for the purpose in the Parish of Saint George, Hanover Square, London.