Originally known as Prairie Point, this town was platted in 1856 by A.C. Hereford, a Virginia native and Mexican War veteran who had arrived in the area in the early 1850s. Located on part of the original James Bowie Survey, it became the second oldest community in Colorado County. In 1861, Hereford's application for a post office for Prairie Point was denied because the settlement lay too close to an existing post office on Amasa Turner's plantation. Turner agreed to move his post office to Prairie Point on the condition that the name Oakland be kept, and the town thereafter became known as Oakland. Situated on the Old Gonzales Road, an important early route from San Felipe to Gonzales, Oakland grew as settlement increased. A school was established in 1859, and churches, stores, businesses, and fraternal organizations soon operated there. The town became a major trading and social center for farm families in western Colorado County before its population began to decline in the 1870s when the railroad bypassed it in favor of Weimar.