Benjamin Cleveland was born in Orange County, Virginia, the fourth child of John and Elizabeth Coffee Cleveland, and was of English descent and Irish descent. He moved to the area which would become Wilkes County, North Carolina in 1769. There, Cleveland built his estate, "Roundabout," near what is today Ronda, North Carolina. He was noted in the early history of Wilkes County, and is known to have 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 the county. A large, heavyset man – around six feet tall and weighing over 300 lbs in his prime – he was called "Old Roundabout.