In 1785, the new county of Marlboro was created within the overarching Cheraws District at the northeastern corner of South Carolina. The District Court was held at Long Bluff, and the lower County Court House of Marlboro County was established a few miles north of Long Bluff along the Great Pee Dee River near Gardner's Bluff. It was simply called Marlboro Court House and only lasted a few years.

The town of Carlisle had begun in 1785 and was soon thriving, so the local populace requested that it become the new County Seat. The exact date is currently unkown. However, it was located on the north bank of Crooked Creek where it crossed the old River Road.

Carlisle soon became called Winnfieldville, which was shortened to Winfield by 1801. Winfield remained the county seat until 1822 - the result of an 1819 Act of Legislation moving the county seat to a more-central location.

As Winfield, the town was granted a U.S. Post Office on January 1, 1801, with Mr. Joel Winfield as the first Postmaster. It remained in operation until April 5, 1822, when the new town called Marlboro C.H. was granted its Post Office.

In 1826, the town of Marlboro C.H. was renamed to Bennettsville, and it has been the county seat ever since. The town of Carlisle/Winfield no longer exists, but a granite monument stands where the courthouse was located.