Originally settled around 1780 as Laurel Gap, this small community was renamed Baileyton in 1892 and incorporated in 1915. It grew into a busy crossroads village with general stores, smith shops, drug stands, saw and planing mills, saddle and harness shops, a flouring mill, tannery, shoe and boot factory, creamery, Masonic lodge, silent movie theatre, and circus grounds. In 1883, Oakland Seminary, the first institution of higher learning in northern Greene County, was chartered here. Affiliated with the Methodist Episcopal Church, it consisted of a two-story schoolhouse, dormitories, and a 1500-seat auditorium, and operated as an inter-denominational, non-partisan, co-educational academy. About 1913, to comply with County High School Law, the seminary consolidated with the County High School Board, and about 1917 Baileyton High School took over the property, using the old grounds and buildings before a new high school was built on this site between 1938 and 1940.