Sleepy Hollow (Upper)

In The Evangelist of Golf, George Bahto commented as follows: "Many of the original Macdonald and Raynor golf holes were named after characters and sites of the story "Ichabod"... The most famous of many legends surrounding Sleepy Hollow is that of the "Headless Horseman." According to the story, the ghost of a Hessian soldier, who was beheaded during the Revolutionary War had possessed the body of Brom Bones, a local schoolteacher. Bones and another townsman named Ichabod Crane were vying for the hand of wealthy heiress Katrina Van Tassel. One fateful night, Crane was confronted by the ghost and chased toward a nearby bridge. As Crane frantically tried to get away, the "Headless Horseman" suddenly stopped and threw his head at him. Crane was never seen alive again."

In the late 1920s, A.W. Tillinghast added seven new holes, which unfortunately resulted in something of a mismatched layout. After a couple of failed restoration attempts around the 1990s, Gil Hanse and George Bahto were called in to perform a major overhaul of the course in 2007.

All twenty-seven holes on the property have now been restored in the style of Macdonald – a trio of replica par threes (Eden 3rd, reverse Redan 7th and Short 16th) benefitting in particular – which proves that new life can be breathed into an old course, providing the right people are involved.

Writing in The Confidential Guide to Golf Courses, Tom Doak commented as follows: "This sprawling course climbs up a ridge, with knockout views of the Hudson River as the backdrop for the short 16th... Not many parkland courses deliver this much drama."

Sleepy Hollow's championship Upper course played host to the U.S. Women’s Amateur in 2002 and the club also staged the Senior Tour's now defunct NYNEX Commemorative tournament between 1986 and 1993.