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Naumkeag was the summer "cottage" of the Choate family who began summering in Berkshire County in the 1870s. Designed by McKim, Mead & White in 1885, this forty-four-room, shingle-style house is filled with original furniture, ceramics, and artwork collected from America, Europe, and the Far East. Joseph Hodges Choate (1832-1917) was a prominent New York attorney. Between 1899 and 1905, he served in England as U.S. Ambassador to the Court of St. James.

Naumkeag is famous for its eight acres of terraced gardens and landscaped grounds surrounded by forty acres of woodland, meadow, and pasture that stretch to the Housatonic River Valley. The gardens and landscaped grounds, first designed in the late 1880s by Nathan Barrett, were transformed and expanded between 1926 and 1956 by Fletcher Steele and Mabel Choate. Separate garden "rooms" include the Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, Chinese Garden, Arborvitae Walk, and Linden Walk. Perhaps the most famous feature of the landscape is Steele's Blue Steps, a series of deep blue fountain pools flanked by four flights of stairs climbing up a gentle hillside and overhung by birch trees.

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