Organized in late 1818, the first, of what was to be an unbroken succession of 188 Skowhegan fairs, was held (of all time) in January 1819, by the original organization known as the Somerset Central Agricultural Society; a name that was continued until 1942 when the official designation became the Skowhegan State Fair. While no record is in existence of what the weather was in January of 1819, it apparently wasn't a determining factor in the attendance as a history of Skowhegan records that the fair attracted the largest crowds ever to have assembled in Somerset County. It is interesting on note that at the time, Somerset County was located in the Commonwealth of Massachusetts; Maine not having become a state until 1820. The name of the first president of the fair was reported as being Eleazer Coburn who was succeeded in 1820 by one Richard Sawtelle. One of the expressed purposes of the fair was to improve the breeding of livestock, with particular emphasis being placed upon the betterment of breeds of horses and cattle, an objective that has been constantly maintained by succeeding fair management.

The present fairgrounds were acquired in 1856 and over the years the original boundaries were extended from time to time, as additional acreage became available. It was on these grounds that past generations viewed models of the first elephants, elegant carriages, displayed by artisans who took pride in their craftsmanship, farm machinery of every description, the early automobile, talking machines, airplanes bicycles, motorcycles and other objects invented and built for better living. In 2005 the fairgrounds was extended once again with the purchase of a lot on Beech Street.