Settlement at Middlefield began in the 1790's on the Outkout, or Long Patent. In 1734, the Patent had been conveyed to George Clarke, Lieutenant Governor of New York. Named Clarksville until 1819, the Middlefield hamlet developed on the east side of Cherry Valley Creek and along an important stage route connecting Unadilla to Albany. The availability of water power was significant in the early prosperity of the settlement, making possible the saw mill, grist mill, and tanneries. The saw mill, built on the southeast creek bank, was powered by water sent through a raceway. On the western creek side, the water was carried under the road through a penstock to power the grist mill. Throughout the nineteenth century, these businesses produced feed, lumber and leather for the growing community. Cider and cheese were made nearby. Owners and operators were active in the social and civic life of Middlefield. In time, fires and floods destroyed the mills, tanneries and dam. Moses Rich, Jr. was the earliest operator of the saw and grist mills, succeeded by Daniel Gilbert and Sumner Ely, who also maintained a carding machine and tannery. Among later owners were F. James Adsitt, Lucian Coleman and Robert McRorie. From 1918-1949, Henry Morton owned the saw and feed mill. The water-powered up and down saw produced boards as large as 4' x 8'. In the late 1930's the flume was being repaired when a summer cloudburst caused substantial flood damage under the building. Repairs were abandoned and the mill dam was torn out. The 3-acre mill property was purchased in 1949 by the School District and the old building was demolished. The grist mill, built on the edge of the road over the water channel, produced flour and feed. In 1892 Lucian Coleman, a skilled mechanic and carpenter, purchased the mills and the adjacent residence. When the grist mill burned in 1905, he salvaged the grinder and moved it to the saw mill. Cheesemaking moved from farm to factory production in the 1850's. Middlefield's cheese factory was next to the grist mill, operating similar to a cooperative. Robert McRorie, Coleman's son-in-law, owned the factory from 1906-1934. He also served as school trustee and town supervisor. The town acquired the factory for its highway garage and built the present day buildings after a 1955 fire.