Originally settled as a farming community during the 1700s in the midst of southern Kentucky’s famed Karst Topography, Oakland-Freeport included early settler families such as the Grimes, Shobe, and Mansfields. Oakland was formally established with the completion of the Louisville & Nashville Railroad in 1859. During the Civil War, the area was allied with the Confederacy, and the 1st Kentucky Brigade, later known as the Orphan Brigade, encamped there in December 1861 to block the Louisville Turnpike and deter Union advancement, though no skirmishes followed. After the war, freed slaves settled north of the railroad in a neighborhood traditionally known as Freeport, where early settler families included the Carpenter, Shobe, and Gossom families. From 1870 to 1900, Oakland became a railroad boomtown and a major shipping point for locally grown tobacco, grain, and livestock, with the rail line serving as the town’s Main Street and commercial development extending along both sides of the 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 reached its greatest prosperity as Kentucky’s major strawberry producing area from 1915 to 1950 and is significant for early settlement in Warren County, agriculture, railroad boomtowns, African American history, and the architectural character of its built environment.