City Directories and History: The original site of Bennettsville near the Great Pee Dee River was called Carlisle, for Richard Carlisle, who came from Virginia about the close of the eighteenth century and settled nearby. It was also sometimes called Winfieldville for Joel Winfield, who served as Clerk of Court in 1787 and as ordinary— now called probate judge—until his death in 1803.12 It was most frequently just the Court House. Upon removal to higher ground the town was named in honor of Thomas Bennett, Governor of South Carolina in 1819 when the legislative act was signed. In 1824 there was a movement to rename the village Washington but this was short-lived.
(Information from: Names in South Carolina by C.H. Neuffer, Published by the S.C. Dept. of English, USC)
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