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.
