Any good gentleman’s farm needs a superintendent to actually oversee all the labor being done to harvest crops and take care of the livestock (because a millionaire owner cannot be burdened to deal with such mundane matters…) When John Howard Whittemore, a successful industrial-era businessman purchased an old farm in Middlebury, Connecticut to spend summers and time out of industrial malaise, he knew that along with a summer home for his family, he would need to build other structures on the 300-acres of rolling hills. The famed architectural firm of McKim, Mead & White was hired by Whittemore to design many of the buildings on the grounds, from the main house, to the superintendent’s cottage to a boathouse. The firm designed this superintendent’s cottage (which currently looks to be getting a new roof) and the creamery in the rear. Both are great examples of the Shingle style in modest, agricultural structures.