Sleepy Hollow Country Club
Designed by A. W. Tillinghast
History
The land along the Hudson River at Scarborough had already known golf before Sleepy Hollow Country Club took its present form. A group of members from the New York area sought a private retreat within reach of the city, and in 1911 they secured the services of A. W. Tillinghast, a young architect just beginning to build the reputation that would later define American golf course design. What emerged from that commission became one of the founding chapters in Tillinghast’s long career.
Tillinghast approached the Scarborough property with the same ambition he would bring to Winged Foot and Baltusrol in the decades to follow. Sleepy Hollow gave him a canvas of dramatic terrain overlooking the Hudson, and the routing he produced there reflected an architect working out his ideas early, before the polish of his later, more famous designs. The club’s membership included men of considerable means and standing in New York society, and the course was built not for public exhibition but for their private enjoyment — a retreat in the truest sense, tucked into the Westchester hills rather than positioned for spectacle.
Over the following century, Sleepy Hollow has remained a private club, guarding its Tillinghast routing with the kind of institutional continuity rare among courses of its vintage. It has not chased championships or sought the publicity that transforms a private layout into a tournament fixture, and its history is consequently one of quiet stewardship rather than headline events. The clubhouse and grounds, including the Rockefeller family’s former estate architecture nearby, have anchored the property’s identity as much as the golf course itself, and the membership has treated preservation of Tillinghast’s original work as a guiding principle rather than an afterthought.
Playing Notes
Expect a walk over genuinely uneven ground — Sleepy Hollow sits on terrain with real elevation shifts and slopes that will put the ball above or below your feet more often than you'd like, so take extra time reading lies before committing to a swing. With 27 holes to choose from, ask the pro shop which nine is playing firmest or driest that day, since routing and turf conditions can vary noticeably across the three loops. Greens here tend to be smaller than what you'd find at a modern resort course, which puts a premium on approach-shot accuracy over sheer distance; missing in the wrong spot can leave a tricky up-and-down rather than a simple chip. Bring comfortable walking shoes and be prepared for a few blind or partially blind shots off the tee where local knowledge of the land helps more than raw power. Wind off the Hudson corridor can pick up in the afternoon, so an early tee time may play more predictably than a late-day round.