[4] The area around Red Oak has been inhabited since approximately 9,000 BCE, beginning with people of the Fourche Maline Culture who were descended from the first Native Americans to migrate from Asia via the Bering Land Bridge.

The combination of poor health and prolonged drought led to the extinction of the Fourche Maline cultures by the early 15th century.

Red Oak became an area of settlement for members of the Choctaw tribe during relocation as part of the Trail of Tears beginning in the 1830s.

Edwards Store became the first post office in Red Oak and was a successful merchantile for both the stage route and the growing community.

At the time it was founded, Red Oak was located in the Moshulatubbee District of the Choctaw Nation.

[6] The arrival of the Choctaw Coal and Railway (later the Choctaw, Oklahoma and Gulf Railroad, subsequently acquired by the Chicago, Rock Island and Pacific Railway) nine miles southwest of Edwards Store led to the relocation of the town to its present site.

With close proximity to the railroad, Red Oak became a thriving and prosperous community in the early 20th century.

Some of the business structures from this era are still in existence, including the Red Oak Library (formerly the post office) and the buildings lining the Main Street business district such as Rustic Customs, Eagle Ridge Camp Store, and Fields Hardware.

[7] According to the United States Census Bureau, the town has a total area of 0.9 square miles (2.3 km2), all land.

(Main article: National Register of Historic Places listings in Latimer County, Oklahoma) NRHP sites in and around Red Oak include Holloway's Station, Edwards Store, the Edwards-Hardaway Homestead and Cemetery, and the address-restricted McLaughlin Site.