Oakland was first settled around 1836 and was located 1.5 miles east of its present location. It was incorporated in 1848.

The town moved when the Mississippi and Tennessee Railroad was built in the 1850s. The settlers named the town after the oak trees in the area.

In the early 1900s, the farms surrounding Oakland produced corn, cotton, vegetables and fruits, and "it is claimed that Oakland pears rival those of California".

Oakland was prosperous, and "one of the best business towns of its size in the State", with two churches, a cotton gin, schools, merchants, and a bank, The Bank of Oakland.