Oakland is a town in Yalobusha County, Mississippi, United States. The population was 527 at the time of the 2010 census.
Oakland was first settled around 1836, and was located 1.5 mi (2.4 km) east of its present location. The town moved when the Mississippi and Tennessee Railroad was built in the 1850s.
During the Civil War, the Battle of Oakland occurred on December 3, 1862, when Union Army General Cadwallader C. Washburn's 1,900 cavalrymen encountered Confederate Colonel John Summerfield Griffith's 6th Texas Cavalry Regiment at Oakland. Both sides withdrew after several hours of fighting.
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.
According to the United States Census Bureau, the town has a total area of 1.4 square miles (3.6 km2), all land.
As of the census of 2000, there were 586 people, 222 households, and 132 families residing in the town. The population density was 409.3 people per square mile (158.2/km2). There were 238 housing units at an average density of 166.2 per square mile (64.3/km2). The racial makeup of the town was 23.72% White, 75.94% African American, 0.17% Native American, and 0.17% from two or more races.