62. Sleepy Hollow Country Club
C.B. Macdonald (1915)/A.W. Tillinghast (1928)
In the mid 2000s, the late George Bahto, who had extensively researched the works of legendary architect C.B. Macdonald, partnered with designer Gil Hanse to remodel Sleepy Hollow Country Club, which consisted of 11 Macdonald-designed holes and seven added in the late 1927 by A.W. Tillinghast. The pair persuaded the club to allow them to rebuilt the entire 18 in Macdonald’s style, reasoning that Tillinghast was well represented elsewhere in Westchester County (Winged Foot, Quaker Ridge and others) but Macdonald was not. The rebuild was done in stages, completed well after Bahto’s death in 2014. Thanks to Hanse, Sleepy Hollow now features some Macdonald “template holes,” an Eden, Knoll, Leven and Road hole, that weren’t even part of Macdonald’s original design.
100 Greatest History: Ranked for first time in 2019-2020. Highest ranking: Current. Previously ranked: No. 89
Watch Golf Digest’s latest “Every Hole At” course videos below:
Panelist comments, Sleepy Hollow Country Club:
"Four of the most beautiful, strategic par 3s you will find in the United States. The third hole and the third-to-last hole will leave you never wanting to leave the greens—they are not only phenomenal green sites but incredibly interesting, undulating greens that are some of the best in the game."
"Some of the coolest and most picturesque holes in the country. The design variety by Macdonald and Tillinghast is off the charts. One of the most fun rounds of golf I’ve ever played."
"Perhaps no course in the US has improved as much as Sleepy Hollow over the past decade. One of the classics of American golf in an incomparable setting, Sleepy Hollow's Gil Hanse's redo has aligned the course as a true C.B. Macdonald design, eliminated misfit holes, and expanded greens to original dimensions."
"Stunning views of the Hudson River from one of the highest points of Westchester County, often times accentuated with "infinity" greens. Ambiance is extremely high with the Vanderbilt mansion clubhouse. The only way to make it better would be overhearing a conversation of Macdonald, Tillinghast and Hanse on the patio having an after-round beverage."
"The collective continuity is great and seen most distinctly in the bunkers and green complexes. While there are many template holes, they've been interpreted so interestingly, such as the downhill redan and the unforgettable short. The incorporation of the natural rock elements in the elevation changes, made for incredible 360 degree vistas. The Hanse renovation is terrific."
All photos: Jon Cavalier