Location: NC 268 at Chatham Street in Ronda
County: Wilkes
Original Date Cast: 1955
Benjamin Cleveland was born in 1738 on Bull Run in Prince William County, Virginia. Tradition holds that he grew up hunting and trading deerskins. Around 1758 he married Mary Graves of Orange County, Virginia; they had three children. In 1769, Cleveland, his brother Robert, and his father‑in‑law Joseph Graves moved to North Carolina, settling on Roaring Creek near present‑day Ronda in Wilkes County. His home, known as the Roundabout, stood just west of modern Ronda on the north bank of the Yadkin River.
When the American Revolution began, the region was still part of Surry County, whose militia consisted of at least one regiment of roughly a thousand men. The earliest record of Cleveland’s service appears in a 1774 militia muster, where he was listed as a lieutenant in Captain John Walton’s company of 87 men. On September 1, 1775, North Carolina’s Provincial Congress created two 500‑man Continental regiments. Cleveland received a commission as an ensign in the newly formed 2nd North Carolina Regiment but declined it, choosing instead to remain with Walton’s Surry County militia company. At the same time, he was serving as chairman of the Surry County Committee of Safety.
In early 1776, eastern North Carolina Loyalists rose in support of a planned British landing at the coast. Three companies of the Surry County militia were mobilized; Cleveland accompanied Walton’s company as far as Cross Creek (modern Fayetteville) before the Loyalists were routed at the Battle of Moores Creek Bridge. That spring and summer, relations between the Cherokee and the southern colonies deteriorated, culminating in coordinated Cherokee attacks along the frontier. North Carolina responded by calling up the Salisbury District militia for a campaign into Cherokee territory. On September 1, 1776, roughly 1,700 North Carolina militiamen marched west under General Griffith Rutherford. Cleveland, now a captain, led a company from the Surry County Regiment. By the end of the expedition, 52 Cherokee towns and their food supplies had been destroyed.
In 1778, Wilkes County was formed, and Cleveland was appointed colonel of its militia regiment. That same year, North Carolina required all suspected Loyalists to swear allegiance or face confiscation of property. Many Loyalists fled into the mountains; Cleveland led aggressive efforts to track them down. According to a deposition by William Sparks, a band of roughly 150 Loyalists raided his family’s home but did not harm them. Cleveland pursued the group, and about thirty were killed, many captured, and at least six later hanged.
Cleveland soon gained a reputation for harsh tactics. In the fall of 1778, he led an expedition into the New River Valley in search of Loyalists, resulting in more hangings. During a campaign on Coxe’s Creek that winter, he repeatedly hung a Loyalist named Williams from a bent sapling to force information from him. Other accounts describe similar treatment of suspected Loyalists and even of female family members. Cleveland was also known to suspend prisoners by their thumbs and to allow mutilation or burning of victims. Under Colonel William Campbell’s broader regional command, the Wilkes and Surry militias took part in widespread destruction of Loyalist and pacifist property. In 1779, Cleveland was indicted for murder by the Salisbury District Superior Court for executing Loyalists without trial, but Governor Richard Caswell pardoned him that November.
By 1780, the approach of Lord Cornwallis’s army and Patriot abuses prompted many Loyalists to flee south into South Carolina. Patriot “Tory‑hunting” intensified as militia units attempted to intercept these groups. In September, Major Patrick Ferguson advanced into western North Carolina to rally Loyalists and threaten the frontier settlements. His messages offered protection to Loyalists and amnesty to Patriots who would lay down their arms. In response, Patriot leaders across southwestern Virginia, eastern Tennessee, and northwestern North Carolina assembled forces to stop him.
Many Piedmont North Carolinians joined Cleveland’s Wilkes County regiment and fought under him at the Battle of King’s Mountain on October 7, 1780. After the Patriot victory and Ferguson’s death, Cleveland claimed Ferguson’s white stallion. Treatment of captured Loyalists after the battle reflected the brutality that had characterized the backcountry war. Some prisoners were hanged, others beaten or mutilated as they were marched northeast.
On April 14, 1781, Cleveland was attacked at his cattle farm on the New River by a Loyalist band led by Captain William Riddle. During the skirmish he reportedly used a local woman, Abigail Walters, as a shield. He surrendered after Riddle promised to ransom him. The group hid in a cave on Riddle’s Knob near Boone. Cleveland’s brother Robert eventually led a party that rescued him; Riddle and several of his men were later captured and hanged from the Tory Oak in Wilkesboro. After this, Loyalist activity in western North Carolina largely collapsed.
Like many Revolutionary leaders, Cleveland held political office as well as military command. He served as a justice of the peace in Surry County beginning in 1774 and, after moving to Wilkes County, was elected to North Carolina’s House of Commons. In 1779, he was elected to the state senate.
A long-running land dispute eventually forced Cleveland from his North Carolina home. William Terrell Lewis sued him in 1778, asserting earlier title to the Roundabout property. After multiple suits and surveys, the courts upheld Lewis’s claim in 1786. Cleveland and his family relocated to the Tugaloo River in South Carolina, where he received a 1793 land grant for his war service.
Benjamin Cleveland died in 1806, having become so heavy that he could no longer ride on horseback. He is buried near the Tugaloo River in South Carolina. He was survived by his wife, two sons, and a daughter.
References:
Martin Armstong, A Field Return of the Regiment of Militia for Surry County…20th June 1774. (1774).
William S. Powell, ed., Dictionary of North Carolina Biography, I, 384—sketch by C. Sylvester Green
Ian Saberton, ed., The Cornwallis Papers: The Campaigns of 1780 and 1781. Vol I, II, III. (2010).
Joseph Graham, General Joseph Graham and his papers on North Carolina Revolutionary history… (1904)
Jason Duncan, Battle of the Roundabout. Battle of the Roundabout - Jason Duncan - webjmd (2022)
William Caldwell, “Isaac Shelby, Patrick Ferguson, and Fire & Sword: The Power of a Good Story.” Journal of the American Revolution. (May 28, 2024)
William Graves, Southern Campaigns American Revolution Pension Statements and Rosters. https://revwarapps.org/
https://www.carolana.com/NC/Revolution/patriot_leaders_nc_benjamin_cleveland.html