|Born||May 28, 1738
Orange County, Virginia
Oconee County, South Carolina
|Occupation||Colonial militia and surveyor|
|Parents||John and Elizabeth Cleveland|
Benjamin Cleveland (May 28, 1738 – 1806) was an American pioneer and soldier in North Carolina. He is best remembered for his service as a colonel in the North Carolina militia during the Revolutionary War, and in particular for his role in the American victory at the Battle of Kings Mountain in 1780.
Benjamin Cleveland was born in Orange County, Virginia, the fourth child of John and Elizabeth Coffee Cleveland. He moved to what became Wilkes County, North Carolina in 1769. He built his famous estate, "Roundabout," near what is today Ronda, North Carolina in eastern Wilkes County. Cleveland was very active in the early history of Wilkes County; he worked as a hunter, trapper, farmer, carpenter, and surveyor. By the time of the American Revolution, Cleveland was the wealthiest and most prominent citizen in Wilkes. A large, heavy set man - around six feet tall and weighing over 300 lbs in his prime, he was called "Old Roundabout."
Cleveland married Mary Graves, a sister of Susannah Graves, second cousin of Susannah Graves. Wills of Joseph Graves and Benjamin Cleveland. Grace S. Green the wife of Revolutionary War patriot and frontiersman, General Joseph Martin, for whom Martinsville, Virginia, is named.
At the beginning of the American Revolution, Cleveland was commissioned a colonel in the North Carolina militia. He was elected to the North Carolina House of Commons in 1778 and to the North Carolina Senate in 1779. Until Lord Cornwallis invaded in 1780, the fighting in North Carolina consisted of guerrilla warfare between patriots and Tories. Cleveland became known as the "Terror of the Tories" for his treatment of Loyalists. In 1779, two Tories looted the home of George Wilfong, a patriot and friend of Cleveland. The Tories used Wilfong's clothes line to chase away his horses. The marauders were captured by Cleveland's men, who had them hanged using the clothes line they had stolen. In revenge, a group of Tories led by Captain William Riddle kidnapped Cleveland. Cleveland's men rescued him and he captured Riddle and two others. All three were hanged from the same tree, which became known as the "Tory Oak" and was an historic landmark behind the old Wilkes County courthouse (now the Wilkes Historical Museum).
In 1780, General Lord Cornwallis led a British army into the Carolinas, and won several victories over the Patriots. Major Patrick Ferguson, one of Cornwallis's most daring commanders, led an army of Tories into the North Carolina mountains to crush the rebels there. A large force of mountain men attacked Ferguson at King's Pinnacle, an isolated ridge on the North Carolina-South Carolina border. Cleveland played a key role in the ensuing Battle of Kings Mountain. According to legend, Cleveland climbed up Rendezvous Mountain and blew his horn to summon some 200 Wilkes County militiamen. He led them in the battle. Cleveland's horse was shot from under him, and Major Ferguson was himself killed in the battle. Cleveland's brother, Captain Robert Cleveland, is said to have rallied the militiamen during the heat of the battle of King's Mountain, contributing to the Patriot victory. Cleveland claimed Ferguson's white stallion as a "war prize", and rode it home to his estate of Roundabout.
He died at his home in Oconee County, South Carolina in 1806 of heart dropsy. An obelisk monument to him stands on private property just north of U.S. Route 123 about 160 yds (145 m) east of the Madison Baptist Church in the Madison Community of Oconee County. He was buried about 1 mi (1.6 km) away in a private cemetery.
First historically accurate depiction
In 2012 artist Don Troiani completed the first historically authentic depiction of Benjamin Cleveland, titled "Benjamin Cleveland’s War Prize." Troiani teamed with experts from across the nation to ensure accuracy. The project was funded by Tennessee businessman and philanthropist Allan Jones and features Cleveland leading his troops back home to Wilkes County on Ferguson’s white stallion after the battle. 
- General Joseph Martin, Daniel Boone Wilderness Trail, danielboonetrail.com
- Alex Sedlander, "Benjamin Cleveland Painting Project Headed by Historian", Cleveland Daily Banner, May 28, 2012
- USGenWeb Cleveland Cemetery and Benjamin Cleveland's will
- Benjamin Cleveland SAR Chapter Photo of the Cleveland Statue in Wilkes County, North Carolina
- Wilkes County website Story of the Tory Oak in Wilkesboro, North Carolina
- North Carolina Historical Marker