Holly Hill developed from a sparsely settled rural community in nineteenth-century Saint James, Goose Creek Parish of the Charleston District after the Revolutionary War, when settlers moved into the parish backcountry near the Four Holes Swamp System, often indenturing themselves to Charleston merchants who held state land grants in order to clear and plant land, build log cabins, or harvest pine sap for turpentine. Despite malaria and yellow fever, some pioneers accumulated extensive landholdings, and roads including Bunch Ford Road, the Old State Road, and Old Gaillard Road linked the area to surrounding parishes, Charleston, and Vance's Ferry on the Santee River. In 1800 Francis Asbury founded the area's first church around a stump pulpit at the head of a gate where tar and other naval products were processed, and over time tar-gate became Target, with Target Church serving as the religious and social center of a growing community. A first school opened in 1855, and after the Civil War a Reconstruction School reopened in the Target Community. Changes in transportation redirected growth when improved routing of the Old State Road in 1823 bypassed Target and the Camden Road was added in 1825; by 1827 Camden Fort Plantation stood at that junction and served some 80 wagons around harvest time, while farmers settled along the new routes. Four ridges or hills crossed this section of road, holly trees were plentiful, and mail addressed to Holly Hills gradually became Holly Hill. In 1886 the crossing of the railroad and the Old Stone Road defined the site of the rural hamlet, and in December 1887 it was chartered as the Town of Holly Hill. The community's county designation also changed over time, from Charleston County to Berkeley County in 1880 and then, by 1910, into Orangeburg County after a successful vote by area citizens. In 1894 the state chartered the Eutawville Railroad to cross Four Holes Swamp, and its 34-mile spur linked Holly Hill, Eutawville, Vance, and Elloree to Charleston's South Carolina Railroad, helping give the settlement access to wider markets.