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Photo By: Carlos Amoedo

‘An almost supernatural backdrop for golf’: Inside the gates of Sleepy Hollow Country Club

Perched hundreds of feet above the lower Hudson River Valley, with never-ending views of the Hudson River and Golden Age architecture beckoning, Sleepy Hollow Country Club is one of golf’s most breathtaking settings. It’s likely your social-media feeds have flashed photos from the 16th tee with the iconic thumbprint green sitting in the fore of the Hudson. We’re here to bring you inside all 338 acres of the tumbling topography with dramatic ridges, rock outcroppings and ravines. Here, we present a comprehensive drone tour of Every Hole at Sleepy Hollow Country Club.

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Carlos Amoedo

A major restoration project overseen by Gil Hanse, Jim Wagner and late historian George Bahto have brought the shine back to this C.B. Macdonald masterpiece. Decades of decline softened some Macdonald features, the result being Sleepy Hollow not appearing on our national rankings from our inaugural list in 1966 until 2013. Even Golf Digest’s Best in State lists did not rank Sleepy Hollow within the 15 best courses in New York.

The long-term project has resulted in Sleepy Hollow steadily climbing our rankings, rising to its current position of 52nd on our most recent ranking of America's 100 Greatest Golf Courses the United States. We wouldn’t be surprised if it comes to move up.

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Jon Cavalier

Among the other distinguishing templates found at the Macdonald gem include the Eden third, his and Seth Raynor’s first reverse Redan (seventh), an enormous Punchbowl 15th green that conjures Fishers Island and the Short 16th.

Enjoy the below video of Every Hole at Sleepy Hollow Country Club:

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Sleepy Hollow Country Club
Scarborough, NY
4.8
33 Panelists
In the mid-2000s, the late George Bahto, who had extensively researched the works of legendary architect C.B. Macdonald, partnered with Gil Hanse and partner Jim Wagner to remodel Sleepy Hollow Country Club, which consisted of 11 Macdonald-designed holes and seven added in 1927 by A.W. Tillinghast. The pair persuaded the club to allow them to rebuild 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 construction was done in stages, completed well after Bahto’s death in 2014. Thanks to Hanse, Sleepy Hollow now features some of Macdonald's “ideal holes," like the Eden, Knoll, Leven and Road holes that weren’t even part of his original design. And it has steadily climbed in our rankings the past few editions. Sleepy Hollow hosted the 2023 U.S. Mid-Amateur.
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