Sleepy Hollow Country Club

Overview: Sleepy Hollow Country Club sits high above the Hudson River in Scarborough, New York, where wooded slopes and long views give the course an unusually dramatic setting for a classic parkland layout. Its design language combines the strategic templates associated with C.B. Macdonald and Seth Raynor, the later work of A.W. Tillinghast and a modern restoration led by Gil Hanse. Punchbowl and thumbprint-style greens, deep movement in the land and changing river views make the course as much about ground and perspective as about raw length.

History: Sleepy Hollow Country Club was formed in 1911, when Macdonald and his engineer Seth Raynor designed and supervised the first nine holes. In the late 1920s, Tillinghast expanded the property to 27 holes, adding another architectural layer to the club's identity. Gil Hanse later prepared a restoration plan that removed overgrown trees, recovered lost views and redesigned selected holes to bring the playing character closer to the early Macdonald and Raynor work.

Did You Know? Sleepy Hollow's current character is the product of three distinct design chapters rather than one untouched layout. Macdonald and Raynor established the first nine, Tillinghast expanded the property, and Hanse's restoration used the earlier architecture as its guide. The result is a course where historical template holes and Hudson Valley scenery remain part of the same visual conversation.