Oakland-Freeport Historic District, Warren County, Kentucky

Oakland-Freeport Historic District, Warren County, Kentucky. National Register of Historic Places. Originally settled as a farming community during the 1700s, Oakland-Freeport is in the midst of southern Kentucky’s famed Karst Topography. Early settlers included the Grimes, Shobe, and Mansfield families., Oakland was formally established with the completion of the Louisville and Nashville Railroad in 1859. , Allied with the Confederacy during the Civil War, the 1st Kentucky Brigade (later known as the Orphan Brigade) encamped the Oakland area in December, 1861. The mission was to block the Louisville Turnpike to deter Union advancement. No skirmishes ensued. , Following the Civil War, freed slaves settled north of the railroad in a neighborhood traditionally known as Freeport. Early settlers in Freeport included the Carpenter, Shobe, and Gossom families. , From 1870 to 1900, Oakland was a railroad boomtown and major shipping point for locally grown tobacco, grain, and livestock. , The rail line also served as Oakland’s Main Street. Commercial development took place along both sides of the rail corridor. The town grew to include a telegraph office, drug store, post office, two general stores, passenger platform, hotel, school, grocery, bank, barbershop, flour mill, and blacksmith shop. Oakland enjoyed its greatest prosperity as the major strawberry producing area of Kentucky from 1915 to 1950. , The Oakland-Freeport Historic District was listed in the National Register of Historic Places in 2004. It is historically significant for its association with early settlement in Warren County, agriculture, railroad boomtowns, and African American history, and for the architectural character of its built environment.