The site of Oakland, on State Highway 7 near present Hall's Bluff seven miles west of Crockett in western Houston County, was first settled in the 1830s. A school began operating there in the late 1870s, and a church was organized around the same time. The community is said to have been named for a grove of very large oak trees on the school and church grounds. At its height around 1900 Oakland had a school, a church, two cotton gins, and several stores. The community began to decline during the early years of the twentieth century, and by the mid-1930s it no longer appeared on highway maps. In the early 1990s only a few widely scattered houses remained in the area.
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