Towards the end of of the 19th century, Colonel Elliot Fitch Shepard, an attorney and founder of the New York State Bar Association, purchased 338 acres high above the Hudson River north of Tarrytown. Shepard’s wife Margaret was the daughter of William H. Vanderbilt and a grand-daughter of Cornelius Vanderbilt, who built the New York Central Railroad in the first half of the century.

The Shepards engaged Stanford White of McKim, Mead and White to design their manor house. White, one of America’s most noted architects, responded with a 75-room structure in the Italian Villa style popular in the late 19th century. It featured elegant formal rooms, including a ballroom, a graceful curving stairway highlighted by a Tiffany stained-glass window, high patterned ceilings, elaborate cornice work and hand-carved wood paneling. The landscape featured sunken, formal gardens that enhanced the panoramic view of the Hudson Valley. Ten stately columns on the grill terrace are the vestiges of the landscaping of that area.

Colonel Shepard did not live to see the construction finished. His widow Margaret and her family occupied the estate until 1910 when she sold it to Willaim Rockefeller and Franklin Vanderlip. They, in turn, invited a group of men to form the Sleepy Hollow Country Club in 1911. In addition to Rockefeller and Vanderlip, the founders included Percy Rockefeller,
Cornelius Vanderbilt, John Jacob Astor, Oliver Harriman, V. Everit Macy,
A.O. Choate and James Colgate.

To build their golf course, the founders turned to Charles Blair Mac-donald, the preeminent golf course architect of the time. After an initial conflict with William Rockefeller about preserving the trees was resolved, Macdonald and his engineer, Seth Raynor, built the course during the extremely hot summer of 1911. At the end of the 1920’s, A.W. Tillinghast, another legendary golf architect, expanded the facilities to 27 holes and in the process created the 8th through the 12th holes of the Upper Course and several holes of the Lower Course.

Sleepy Hollow underwent extensive changes in the 1960’s when the members voted to move golf activities from another building on the property and build a new wing at the northern end of the Vanderbilt clubhouse. The clubhouse addition which included locker rooms, a grillroom and a pro shop, was finished in 1962 and was recent-ly renovated.
In addition to golf, the club’s current amenities include ten tennis courts, two swimming pools, three squash courts, four platform tennis courts, a 40-horse stable from the Vanderbilt era, two indoor riding arenas and shooting facilities for skeet and trap.

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