According to information published in 1874 there was held in Livingston an Agriculture Association Fair before the War Between the States. This fair ceased operate during the war and had not been revived in 1874. This fairground was located west of the town at that time on lands now located just north of the present county nursing home on Bilbrey Street. These early fairs were held in connection with horse races. The showing of fine horses was one of the special attractions and the sessions of the fair drew large crowds.
The Overton County Agricultural and Mechanical Fair was organized in Livingston in 1882. This fair ground was located in the western part of the town on either side of current Bilbrey Street. The plot for the fair grounds was surveyed in 1883. Col. John M. Barrett was the first president and Hudson S. Estes was the secretary and treasurer. Fairs were held regularly for 19 years at this fair ground and were attended by large crowds from Overton and surrounding counties and from Kentucky. The exhibits on display were numerous and represented with credit the agricultural and mechanical development of the county at that time period. The brass bands and fine horses shown were special attractions at these fairs.
An early account of a catalog of the fourteenth annual exhibition of this fair held on October 1,2,3, 1896 shows the following officers; Elihu Wells president, J.N. Cannon vice president, L.N. Oakley secretary and treasurer, R. A. Dale, general superintendent, the directors were L.D. Bohannon, W. J. Matthews Jr., R. L. Mitchell Jr., Thomas W. Carlock and A. F. Eldridge. John Cook was ticket agent, J.P. Bilbrey and Thomas Richards keepers of the stock gate, J.W. Hall keeper of the ring gate and J.J. Phillips keeper of the foot gate the admission was 25 cents.
Down thru the years Overton County has held a number of agricultural fairs in Livingston. These fairs were usually held on the grounds of Livingston Academy with little general plan for the arrangement of the various exhibits and displays. The money for the premium lists of these fairs was usually donated by business men of the town with a small amount of State aid to fairs. The Overton County Agricultural Free Fair was reorganized in 1938 and this fair drifted along for a few years with just the usual amount of support and interest with little shown for a few years during World War II.