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Bryan County was formed in 1907 with its county seat at Durant, Oklahoma. According to the Oklahoma Historical Society's Encyclopedia of Oklahoma History & Culture Bryan County was "named for Democratic presidential candidate William Jennings Bryan, a contributor to the 1907 Oklahoma Constitution" ( Milligan 1). Bryan County was originally Choctaw land and was settled by them shortly after their first removal, 1831-1832; however, the one-fourth of the western portion of the county was allotted to the Chickasaw at the time of their removal, 1837-40.

Bryan County has a long educational history. In 1845 the Choctaws established Armstrong Academy (for boys) - Which also served as the capital of the Choctaw Nation during the Civil War- and in 1852 the Chickasaw established the Bloomfield Academy (for Chickasaw girls).It was in Durant in 1909 that the first institution of higher learning in southeastern Oklahoma, Southeastern Normal School, present-day Southeastern Oklahoma State University. Then in 1910 the Choctaw established the Oklahoma Presbyterian College, which is now the site of the governmental offices of the Choctaw Nation.

The County and many of the towns located therein were developed as part of the transportation industry. According to Miligan , "serveral towns sprang into existence with the arrival of the first north-south railroad, the Missouri Kansas and Texas Railway (MK&T, or Katy). Choctaw and White businessmen built the towns of Caddo, Durant, Calera, and Colbert, near the former Colbert's Ferry crossing on the Red River, to serve the train traffic" (Milligan 2).