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Chesterfield County was formed by the County Court Act of 1785, when Cheraws District was divided in Chesterfield, Darlington, and Marlboro counties. Textbooks will tell you that Chesterfield County was named after Lord Chesterfield, Philip Dormer Stanhope, a close friend of King George III; however, local tradition states that the Craig family, who originally inhabited the county seat, was influential in naming the county after the county from which they came, Chesterfield County, Virginia. Population grew slowly with Welsh, French Huguenots, Scots-Irish, Germans, and English moving in mostly from the other colonized areas.

On November 19, 1860, Chesterfield County held the first secession meeting in South Carolina. The ensuing war took its toll upon the state and the county. It is commonly known "that Sherman expected to exact vengence from the original secessionists, who, he said, bore a major share of the blame for the war." This he did, and on March 2, 1865, entered Chesterfield County with a vengence.

In Chesterfield, the county seat, the courthouse, jail, academy, and other buildings, were burned to the ground. In Cheraw, the business portion, except for one house, was also burned down. Cotton, crops, food, and livestock were either stolen or destroyed. In a letter during reconstruction, Thomas Powe of Cheraw to Governor Orr, Powe brought that "every house in Chesterfield District, with the exception of two cabins, were visited by Sherman's soldiers and the bare mention of this fact speaks volumes."
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