In 1819, the South Carolina General Assembly authorized moving the Marlboro County courthouse to a more central location. The site chosen was a three-acre apple orchard on a bluff above Crooked Creek. Robert Mills — the South Carolina architect who would later design the Washington Monument — drew up the courthouse plans. The streets of the new town radiated outward from the courthouse square, one of the largest in the state. The town took its name from Thomas Bennett Jr., then governor of South Carolina. The Mills building was replaced in 1852, replaced again in 1884, and enlarged in the 1950s. The current courthouse holds the 1884 Second Empire core inside two-story red brick wings and a clock steeple, all designed by Bennettsville architect Henry D. Harrall.

Bennettsville grew on cotton, and cotton grew on the labor of enslaved African Americans. Many were brought to this upland region from the Carolina Lowcountry, carrying their Gullah culture with them. Others were transported north by slave traders from the Upper South. The cotton gin made short-staple cotton profitable on the uplands, and large plantations spread across the Pee Dee. The lives of the enslaved people whose labor built this town's wealth are visible mostly in the records kept by the families who owned them — names, ages, prices — though those records also preserve the genealogical traces that descendants today use to find their families. The county courthouse holds records dating to 1785, available for that work.

In March 1865, during the last year of the Civil War, Union troops occupied Bennettsville. General William T. Sherman used the Jennings-Brown House and the first County Courthouse as his headquarters during the brief stay. The new courthouse, somehow, was not burned. Local lore says Sherman spared it as a working symbol of civil order; documents suggest the army was simply moving fast toward North Carolina. Either way, the courthouse survived, and so did the records inside it. Two decades later, in 1885, Duncan Donald McColl financed Bennettsville's first railroad, bank, and textile mills, kicking off the King Cotton era that made the town the center of one of the richest agricultural districts in South Carolina.

The Bennettsville Historic District was added to the National Register of Historic Places in 1978. Its contributing buildings tell the architectural history of the town: the Jennings-Brown House (1826), the Female Academy (1830), the Medical Museum (1902), the Murchison School (1902). Queen Anne and Beaux Arts homes line the streets that radiate from the courthouse square. Five separate properties around town hold individual National Register listings — Appin, Magnolia, the Robertson-Easterling-McLaurin House, and the Jennings-Brown House among them. The town never grew wealthy enough to tear its historic buildings down for new ones, and that accident of economic history has left it with one of the better-preserved 19th-century streetscapes in the South.

The library named for Marian Wright Edelman sits on 4.4 acres at Marlboro Street and Fayetteville Avenue, adjacent to the 1902 Murchison Building. Its front tower aligns with the Murchison tower. Inside are 60,000 volumes and two conference rooms, paid for partly with $1.325 million in federal funding. Edelman herself returned for the opening. She had spent decades arguing, in Senate hearings and presidential commissions and her own books, that no child should be measured by the wealth of the family they were born into. Her hometown — a place that had once denied her family's church members hospital beds — built her a library in 2010. The town has produced others worth knowing: comedian Aziz Ansari grew up here. Bank of America CEO Hugh McColl is from here. So is historian Chancellor Williams, whose work on African civilizations shaped a generation of scholarship. Bennettsville keeps growing people who leave and become useful.