Fairland was laid out along the St. Louis and San Francisco Railway (Frisco) tracks that were laid from Missouri to Vinita in 1871. The town originally covered 225 acres and consisted of a few businesses and residences that had moved there from the Prairie Springs area.
By the time Oklahoma became a state, Fairland was an active farming community. In 1912, the Missouri, Oklahoma and Gulf Railway, later the Kansas, Oklahoma and Gulf Railway (KO&G), constructed a track through Fairland that crossed the earlier Frisco line.
Agriculture remained the mainstay of the local economy until the end of World War II. In 1945, B. F. Goodrich opened a tire manufacturing plant near Miami that became the major contributor to Fairland's economy. The town organized a volunteer fire department and built a sewer system about 1950. The Fairland School district absorbed several smaller districts. However, KO&G abandoned and removed its tracks about the same time.
The Goodrich plant closed permanently in February 1985. The loss to Fairland's economy was offset by the opening of several communities on the shore of Grand Lake O' the Cherokees.