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Bishopville was known as Singleton’s Crossroads for more than a decade before it was renamed in honor of Jacques Bishop. The 465 acres (1.88 km2) of land had been granted to Jacob Chamber by the state of South Carolina in 1786. Daniel Carter later purchased the property and then sold it to William Singleton in 1790.

The tavern owned and operated by Singleton and his wife sat at the intersection of Mecklenburg Road, now Church Street, and McCallum Ferry Road, now Main Street. This tavern was a stop on the stagecoach route between Georgetown and Charlotte. (Now this intersection involves Highway 15, which at one point was the premier north-south route from New York to Miami.) In 1798, William Singleton died, leaving his wife the owner of the tavern until her death in 1820. A year later in 1821, the property was sold to Bishop. During this time period, the area around present-day Bishopville was said to be composed of mostly wilderness, with only a few scattered, primitive houses.

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