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1906 Vanderbilt Cup hairpin turn in Old Westbury
Westbury was founded by Edmond Titus, and was later joined by Henry Willis. Willis, one of the first English settlers, named the area after a town in his home county of Wiltshire, England. Westbury had been a Quaker community of isolated farms until the railroad came in 1836. After the Civil War, the New York elite discovered that the rich, well wooded flat countryside of the Hempstead Plains was a place to raise horses, and to hunt foxes and play polo at the Meadow Brook Polo Club. The Village of Old Westbury was incorporated in 1924, separating itself from Westbury, the adjacent area that housed many of the families of the construction and building staffs for the Old Westbury mansions.
Westbury House was the residence of Henry Phipps' eldest son, John Shaffer Phipps. Today, the property is operated as Old Westbury Gardens. Robert Low Bacon built 'Old Acres' in the style of an Italian villa. Other landowners were Thomas Hitchcock and his family, Harry Payne Whitney and his wife the former Gertrude Vanderbilt, founder of New York's Whitney Museum, at Apple Green (formerly a Mott house), Cornelius Vanderbilt Whitney, whose estate is now subdivided into the Old Westbury Country Club and New York Institute of Technology. The architect Thomas Hastings built a modest house for himself, 'Bagatelle', in 1908. A. Conger Goodyear, then president of the Museum of Modern Art in New York City had a house built in 1938 by famed architect Edward Durell Stone, who also destined the building for Conger's museum. In 2003, the A. Conger Goodyear House was added to the National Register of Historic Places to protect the structure from being demolished to subdivide the expensive land surrounding it. The estate of Robert Winthrop, an investment banker and member of the Dudley–Winthrop family, for whom Winthrop-University Hospital was named, has been similarly preserved. Part of Gertrude Vanderbilt Whitney's estate and her sculpture studio has been preserved and maintained by one of her grandchildren, Pamela Tower LeBoutillier.
When Robert Moses was planning the Northern State Parkway, the powers of Old Westbury forced him to re-site it five miles (8 km) to the south. Once the parkway was completed, many residents found it to not be the eyesore they had been anticipating and regretted making their commutes more inconvenient than necessary. In the 1950s, the state purchased land from Charles E. Wilson, a former president of General Motors who needed to sell off his Old Westbury estate to pull himself out of financial crisis and relocate to the nation's capital to serve in President Dwight D. Eisenhower's cabinet. The land, which runs along an edge of the village, was used for the Long Island Expressway.