The very first Cumberland Fair was held for two days on October 10th and 11th of 1868 in the center of town in back of what is now Greely Junior High School. The land was provided by Capt. Enos Blanchard. His house is now Doc's Cafe and Marketplace on the corner of Tuttle Road and Main Street. The ladies of the town had an opportunity to show all who attended what marvelous cooks they were, and what fine needlework their fling fingers could provide. Farmers brought their biggest and best-tasting vegetables. Those men with working steers could show off the strength and coordination of their animals at the ox pulling contest. Local horsemen raced their finest steeds on Main Street from the junction of Tuttle Road and Blanchard Road to Greely Road. And so it began.
Just a few years later, a 1/3 mile track was laid out and constructed in the pasture behind the Center burying ground.
A group of prominent Cumberland citizens, including Eliphalet Greely (benefactor of Greely Institute, now Greely High School), petitioned the State of Maine to formally incorporate the Cumberland Farmer's Club. The petition was enacted upon and approved in February of 1875.
World events had few bearings on how things worked, even with the Fair. Fire destroyed the hall in 1917. Due to the involvement of World War 1, and an outbreak of the flu, the hall was not rebuilt until 1921.
In 1938 a new grandstand was built. In 1941 it was voted that a clay track would be built. Clay is still the composition of the track today. In 1945 electricity was installed. 1946 saw telephones installed; all three of them; 1947 was the year that the grandstand at the pulling ring and the restaurant were built; in 1948 lights were installed around the track for night racing; 1953 was the first year that the calf scramble was held; 1969 was the year that the current Exhibition Hall was built, and a few years later it was added on too. The original hall was designed for use by 4-H, but it is still owned by The Cumberland Farmers' Club. Glass was installed in the Grandstand in 1961 and the Ed Wilkinson property, where the old farmhouse is, was bought. A year later a new horse paddock was built on that property. Work is an ever present factor with the Fairgrounds, as there is always something to be painted, moved, enlarged, shingled or built on the Fairgrounds.