5. Naumkeag

Naumkeag is a quintessential estate from the Gilded Age, an architectural masterpiece by the prominent Mckim, Mead & White firm. The estate was the summer home of lawyer Joseph Hodges Choate, who purchased the land from New York lawyer David Dudley Field in 1884. Interestingly, Field, whom Choate persuaded to sell the 40 acres, had been Choate’s adversary in legal cases concerning Boss Tweed!

The task of designing and constructing the “summer cottage” was given to Choate’s friend McKim, and was completed in 1887 at the cost of $35,000. Interestingly the proposal of Frederick Law Olmsted (the co-designer of Central Park), who was originally tasked with landscaping the estate, was rejected due to his idea to place the house halfway down the hill, in favor of the self-taught designer Nathan Barrett. Implemented between 1884 and 1894, Barrett’s design comprised of a formal flower garden, a broad meadow sloping down the hill, an orchard, and a family cemetery plot at the bottom of the hill, while the main estate house was on top of the hill.

After Choate’s death, minor design changes to the estate were made by his daughter, Mabel. Upon her death in 1958, the estate was bequeathed to the Trustees of Reservations, such that it would be “an authentic representation of the times and manner of living which it now [1958] reflects.”