Sleepy Hollow Country Club

Sleepy Hollow Country Club is a historic country club in Scarborough-on-Hudson in Briarcliff Manor, New York. The club was founded in 1911, and its clubhouse was known as Woodlea, a 140-room Vanderbilt mansion owned by Colonel Elliott Fitch Shepard and his wife Margaret Louisa Vanderbilt Shepard.

The 338 acres of “Washington Irving” hills and woodlands that make up the Sleepy Hollow Country Club were once known as Woodlea, the country estate of Colonel Eliot F. Shepard, an attorney and founder of the New York State Bar Association. 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 1893 Colonel Shepard engaged one of America’s most noted architects, Stanford White, to design the manor house which today is the main clubhouse. The entire estate was purchased in 1910 by Mr. William Rockefeller and Mr. Frank A. Vanderlip, who in May 1911, sold and turned it over to the organizers of The Sleepy Hollow Country Club.

To build their golf course, the founders turned to Charles Blair Macdonald, the preeminent golf course architect of the time.Macdonald and his engineer, Seth Raynor, built the course during the summer of 1911 and it opened for play in the spring of 1913. The Course was immediately recognizes as one of the finest in the country. 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 11th holes of the Upper Course and several holes of the Lower Course.Recent renovations by Gil Hanse and George Bahto restored the original character to all twenty-seven holes.The Upper Course was host to the Champion’s Tour “Commemorative” from 1986 through 1993.The 2002 US Women’s Amateur Championship was also contested on Sleepy Hollow’s beautiful championship golf course.

In addition to golf, the clubs current amenities include a 1,700-square foot indoor/outdoor temperature-controlled learning center for golf, ten tennis courts, two swimming pools, four squash courts, four platform tennis courts, fitness center, a two level horse stable from the Vanderbilt era, two outdoor riding rings, one indoor riding ring arena and shooting facilities for skeet and trap.

The Woodlea Clubhouse began development in 1892 as a Vanderbilt Mansion owned by Colonel Elliot Fitch Shephard, the owner of the Mail and Express newspaper and founder of the New York Bar Association. The mansion was purchased in 1910 by Frank Vanderlip and William Rockefeller, and in 1911, Sleepy Hollow Country Club was founded by a board of directors, which included John Jacob Astor IV, Cornelius Vanderbilt III, Edward Julius Berwind, and others. Throughout the years, Sleepy Hollow Country Club has gone through a number of renovations and changes to being one of the top-rated golf courses and country clubs both in New York and the United States

This Westchester County course has always enjoyed a spectacular component to it, courtesy of breathtaking views of the Hudson River. What it lacked was playing interest from 50 yards and in to its greens. That changed in 2016 when Gil Hanse embarked on a two-year project to imbue the greens with a C.B. Macdonald flair that, well, even Macdonald would appreciate.

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