Oakland is just southwest of the intersection of Farm roads 532 and 2144, on the Lavaca county line eight miles south of Weimar in northwest Colorado County. It is on a site originally granted to James Bowie. As early as 1844 the community, then called Prairie Point, had a store on the stage line between Columbus and Gonzales. There was a small log schoolhouse in the community by the 1850s. The town was laid out by A. C. Herford in 1857. When Herford could not secure a post office because of the town's nearness to other post offices, Amasa Turner agreed to move his post office in Lavaca County to Herford's location on the condition that the post office retain the name Oakland, which Turner had chosen in honor of David G. Burnet's home. A Masonic lodge was established in the community in 1861, and when a two-floor schoolhouse was built in the 1870s, the upper floor was used for Masonic meetings. The building was also used as a church. In 1882 Oakland Normal School was opened to educate black school teachers. In 1884 the town had 200 inhabitants, a public school, three general stores, a saloon, a steam cotton gin, two churches, and grist and saw mills. In 1900 Oakland had a population of 264, and in 1904 the community had one school with sixty-five white pupils and another school with eighty-one black pupils. In the 1930s Oakland had seven businesses, a church, and 200 inhabitants. By 1950 the population had dropped to 100 and the number of businesses to three. The population was ninety-five in 1970 and eighty in 1974. In 1981 Oakland had a number of dwellings and three churches, and its population was estimated at eighty from 1974 through 2000.