Fairdale Farms is representative of Vermont's mid-twentieth-century local dairies, of which there are few surviving examples. It is of additional interest because it evolved from a gentlemen's farming enterprise. In 1890 James S. Colgate, New York City financier and grandson of the founder of the Colgate Soap Company, decided to live part-time in Bennington, a choice that must have pleased his wife, Hope Hubbell Conkling, of West Bennington. He began purchasing a number of farms, including this one, and for the next fifty years raised dairy cattle, sheep, and hogs, subsidizing the farms throughout an increasingly depressed agricultural market. The only structure retained from the original farm, organized in 1850 by Elijah Day Fillmore, was a banked horse barn with board-and-batten siding and a slated gable roof with the initials “E.D.F.” in red slate (now the visitors' center). The Colgates moved a c. 1810 Cape-type dwelling onto the lot for housing a hired man and his family and built an office, three cattle barns, and a sheep barn. Several of the cattle barns were built by the contractor and design team of Walter and Erwin Dunham of Bennington. Colgate arranged his will so that employees could purchase the Colgate Farms properties upon his death in 1944. This occurred under managers Robert Holden and Morris Douglas, who helped organize Fairdale Farms, which moved all operations into dairying and began bottling milk under that trade name. The c. 1945 milk-processing plant is a one-story, sprawling structure with industrial steel sash but in keeping with Bennington's Colonial Revival tastes with its quality Flemish bond brick facade and a centered colonial frontispiece. Fairdale Farms added a moderate-sized, dairy free-stall pole barn in the 1960s, expanding this collection of agricultural buildings that trace the evolution of a tenant farm into a twenty-first-century agricultural business.