History
Did Washington Irving’s infamous tale of a headless horseman riding through the tangled oaks on a mysterious Halloween night actually occur on the grounds of the club? …Well, one may never know, but that legend as well as so many others, is woven into the fabric of what is The Sleepy Hollow Country Club.
The 338 acres of “Washington Irving” Hills and the woodlands that make up The Sleepy Hollow Country Club were once the estate of Mr. Butler Wright. The Butler family home was situated to the north of the current pool complex and for many years served as the Club’s golf house.
The estate was purchased by Colonial Elliot F. Shepard and his wife Margaret Louisa Vanderbilt Shepard, granddaughter of Commodore Cornelius Vanderbilt. The cornerstone for the mansion overlooking the Hudson that would become known as “Woodlea” was laid in 1893 by the world renowned architectural firm of McKim, Mean, and White.
In 1911, a group of men of legendary wealth and structure formed the Sleepy Hollow Country Club. Among them were William Rockefeller and his son Percy, Cornelius Vanderbilt, John Jacob Astor (who died on the Titanic in 1912), Franklin Vanderlip, Oliver Harriman, V. Everit Macy, A.O. Choate, and James Colgate.
Golf course architect, Charles Blair Macdonald and his engineer, Seth Raynor, designed and oversaw the construction of the initial 9 holes of golf in 1911. In the late 1920’s A.W. Tillinghast expanded the course to 27 holes. The club received Golf Digest’sTM “America’s Best New Course 2008” award in the “Best New Remodel” category. In 2011 the club achieved recognition in GOLFWEEKTM magazine as one of “America’s Top 100 Classic Courses”.
In the year 2006, Sleepy Hollow Country Club was rated 57th of the 100 most prestigious private clubs in America by Golf Connoisseur Magazine and has consistently been awarded the distinction of being named a Platinum Club of America (Top 100 Country Clubs) by the Club Leaders Forum Magazine
