Wakefield initially served under Captain William Penland, whose surname also appears in the records as Pentland. His company marched to Cathey’s Fort and participated in operations against the Cherokee west of the Blue Ridge Mountains. During a hunting or scouting expedition near Bull Mountain, Wakefield shot a Cherokee warrior and was then shot in the back by another. His companions retreated to the fort with his horse, believing him to be dead. Despite his wound, Wakefield reported that he reached the fort six days later and was subsequently taken home to recover.
After regaining his health, Wakefield returned to service. He joined a light horse company commanded by Captain Thomas Kennedy and served under General Griffith Rutherford in operations intended to suppress Loyalist activity and take prisoners. When reports reached Rutherford that Cherokee warriors were threatening the frontier settlements, Wakefield was among approximately one hundred men sent home to protect the region.
In June 1780, Wakefield attempted to join the American forces gathering against Loyalists at Ramsour’s Mill. He marched with Captain John Russell’s company but missed the battle because, according to his pension declaration, their guide led the company incorrectly. Wakefield nevertheless continued to participate in short expeditions against Loyalists who threatened families and settlements in western North Carolina.
Later in 1780, Wakefield joined Captain John Russell’s company in Colonel Joseph McDowell’s regiment for the campaign against British Major Patrick Ferguson. The regiment marched first to the Cowpens and then to Kings Mountain. Wakefield fought in the Battle of Kings Mountain on October 7, 1780, and received a slight wound in the mouth. After the American victory, he helped escort British and Loyalist prisoners toward the Moravian settlements and then to Morganton, North Carolina, where Colonel McDowell discharged him.
On March 20, 1778, during the Revolutionary War, Henry Wakefield married Elizabeth Alexander, a daughter of William and Elizabeth Alexander. They reportedly had eight children, although their names are not included in the surviving pension transcript. Elizabeth died around 1791.
On October 25, 1791, Henry married his second wife, Mary Simpson, in Burke County. William Pentland, a justice of the peace, performed the ceremony. A family Bible record submitted with Mary’s later widow’s pension application identifies ten children born to Henry and Mary between 1792 and 1816: Agnes, Isabella, Henry, Simpson, the twins John and Alexander, Silas Burkes, James Madison, Polly, and Thomas Jefferson Wakefield.
Henry remained in Burke County until approximately 1796 or 1797, when he moved his family to Sumner County, Tennessee. He later settled in Smith County, Tennessee, where he spent the remainder of his life.
On August 28, 1832, Wakefield appeared before the Smith County Court of Pleas and Quarter Sessions and applied for a federal pension under the Revolutionary War Pension Act of 1832. At that time, he stated that he would be eighty-one years old the following May. He acknowledged that his advanced age and failing memory prevented him from recalling the precise dates and lengths of his various periods of service. In a supplemental declaration dated May 21, 1833, he estimated that he had served for no less than three years. The federal government ultimately credited him with one year of service as a private in the North Carolina militia and awarded him a pension of forty dollars per year, effective March 4, 1831.
Henry Wakefield died in Smith County, Tennessee, on either November 12 or November 13, 1850. His widow gave November 12 as the date, while two of their sons later stated that he died on November 13. He was approximately ninety-eight years old.
On September 30, 1851, Mary Wakefield applied for a widow’s pension in Macon County, Tennessee. Her application was supported by the family Bible record and by testimony from James Simpson, a relative who stated that he had attended Henry and Mary’s wedding in Burke County in 1791. These pension documents preserve both Henry Wakefield’s account of his Revolutionary War service and important information concerning his family and migration from Virginia to North Carolina and, ultimately, Tennessee.
Henry Wakefield is the Revolutionary War Patriot ancestor of Dr. John Wakefield, a member of the Kings Mountain Chapter.