The town of Bennettsville was established in 1819, when the Marlboro District courthouse was moved from its original site on the Pee Dee River to a more centralized location. The new site, a three-acre plot on the stagecoach road between Society Hill and Fayettville, North Carolina, became the new county seat. It was named for the South Carolina governor at the time, Thomas Bennett Jr. of Charleston, who opposed the slave trade and would urge restraint during the 1822 Denmark Vesey slave revolt.

By 1860, Bennettsville was a growing country town in a region of cotton plantations and small farms. It suffered a setback in 1865, however, when General William T. Sherman's army passed through Marlboro County and burned much of Bennettsville. In the 1880s, arrival of the railroad restored prosperity and the town soon boasted a cotton mill, cottonseed oil company, and a new bank.

In the 20th century, U.S. Highway 15 brought a steady stream of automobile traffic through town, and in World War II, the Army Air Corps constructed a training base at nearby Bennettsville-Palmer Air Field. As the number of cotton growers and small farmers declined in the postwar years, a variety of industries were recruited into the area. Meanwhile, the descendants of the slaves who had worked the region's cotton plantations gave Bennettsville one of South Carolina's highest per capita populations of African Americans, comprising more than half the city's residents.

Today, the Bennettsville Historic District which includes much of downtown Bennettsville, preserves the history of Bennettsville and surrounding Marlboro County. The Marlboro County Historical Museum, located at 123 S. Marlboro Street, is housed in a historic Victorian home and features exhibits tracing local history, including Native-American artifacts, tools and equipment from area plantations and farms, military artifacts, and a children's room with antique toys.

The adjacent Jennings-Brown House, built in 1827 by a local physician, displays period furnishings and a rare, painted bedroom ceiling. In 1865, it was the temporary headquarters of Major General Franklin Blair who commanded the XVII Army Corps when Sherman's Federal army marched through Marlboro County. Across the street is the Medical Museum, a former doctor's office, which features restored examination rooms from the 1920s and 1950s.

Nearby are several historic churches and the Bennettsville Female Academy, a restored Civil War-Era women's finishing school which displays educational artifacts from the era. The most familiar historical landmark in Bennettsville, however, is the Marlboro County Courthouse which towers over the downtown with an architectural design reminiscent of Philadelphia's Independence Hall. It is the fourth courthouse to exist on this site and enlarged an existing courthouse when constructed in 1951.

The D.D. McColl House, located at 304 West Main Street, is a turreted brick home built in 1826. In 1871, it was bought by a local attorney and business leader, Donald D. McColl, who established a bank in Bennettsville, and was instrumental in bringing the railroad to the area. His descendant, born is Bennettsville, is Hugh McColl, who was chairman of the Bank of America. Today, the McColl House is occupied by the Bennettsville Visitors Center and Chamber of Commerce, where visitors may obtain information about the Bennettsville Historic District.

Historic Registry: National Register of Historic Places