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Initially settled as a farming community during the late 18th century, Oakland was formally established with the completion of the Louisville & Nashville Railroad in 1859. From 1870 - 1900, Oakland was a railroad boomtown and major shipping point for locally grown tobacco, grain, and livestock. Commercial development took place along both sides of the rail corridor, and the town grew to include a telegraph office, drug store, Post Office, two general stores, passenger platform, hotel, school, bank, barber shop, corn mill, and blacksmith shop. Oakland enjoyed its greatest prosperity as the major strawberry producing area of Kentucky from 1915 to 1950.

Oakland and the neighboring Freeport Community were listed in the National Register of Historic Places in 2004. The area is historically significant for its association with early settlement in Warren County agriculture, African-American History, and architecture.

Though much of the Historic Commercial District was destroyed by fire in the early twentieth century, the City Hall, Post Office, General Store, bank building - now used as a Free Mason Lodge - as well as several old homes remain. Many of the City's current residents chose Oakland for its quiet charm and quaint village atmosphere.