Sleepy Hollow (Upper) - New York - USA

Sleepy Hollow Country Club,
777 Albany Post Road,
Scarborough,
New York (NY) 10510,
USA


  • +1 914 941 8070

  • Golf Club Website

  • 2 miles S of Scarborough on the E side of the Hudson River

  • Members and their guests only

  • William Nitschke

  • Charles Blair Macdonald and A.W. Tillinghast

  • David Young


Designed by Charles Blair Macdonald, with Seth Raynor as foreman, the legendary golf layout at Sleepy Hollow Country Club sits high above the Hudson River on a 338-acre estate that was purchased by William Rockefeller and Frank Vanderlip a year before the course opened for play in 1911.

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 renovated 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.
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Reviews for Sleepy Hollow (Upper)

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Description: Designed by C. B. Macdonald and Seth Raynor, the legendary golf course at Sleepy Hollow Country Club sits high above the Hudson River on a 338-acre site formerly owned by William Rockefeller and Frank Vanderlip… Rating: 5.7 out of 6 Reviews: 6

I had the pleasure of playing Sleepy Hollow a few weeks ago. I consider myself a pretty tough critic (check out my other reviews), but this is a vastly underrated course and deserves a Top 25 spot in the U.S. The course is picturesque and some photogenic courses become overrated, but as good as the photos are, it still doesn't do the course justice.

The only criticism I can see is that the Tillinghast holes are very different than the MacDonald holes. On the other hand, one can argue that it gives the course more variety and makes it more interesting.

While the par 3 #16 steals the show because of its beauty, the par 3 #7 is far more fun.

6 / 6
Sleepy Hollow (Upper)
June 27, 2018


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This is a venue that has gone through many architectural changes, and now 4 architects can stake their claim to crafting its current layout. Eleven of the original eighteen holes laid out by CB. MacDonald remain today as part of the 18 hole upper course. CBM did build a full 18 holes, however 4 holes were sold off 15 years after the course was opened and three of the original holes were moved to the lower course where they exist today and are very playable. In 1927 Tillinghast added 5 holes (8-12) and shortly afterwards Tom Winton added two, what are now the first and last. While the holes that Tilie added are solid by their own right, they visually break the flow of the MacDonald architecture and really stick out. All of the greens are presently being rebuilt by Gil Hanse, who oversaw the course's 2007 restoration and, when complete, will be in the MacDonald style.

Sleepy Hollow Country Club - Photo by reviewer

Unfortunately, the course at Sleepy Hollow CC is a far cry from what it must have looked like 100 years ago, and feels somewhat disjointed. Today’s layout is a random collection of different architect’s work pieced together. The routing has changed a lot too throughout the decades when parcels of land were being exchanged. Of the 11 MacDonald holes, many of the template holes are on display, including a downhill reverse Redan, a short hole and a Punchbowl green which are truly fabulous. The holes overlooking the Hudson River are jaw-dropping, as is the dramatic changes in elevation. Sleepy Hollow has world-class visuals and architectural features primarily created by CB MacDonald and one wonders why it doesn’t appear on Top 100 listings. However, when you consider the intermittent holes and green complexes created by other architects, you begin to see how the argument breaks down and the course loses its way from a memorability perspective. The last 4 holes get most of the glowing attention, but the debate needs to be comprehensive across all 18 holes to be a true contender. The clubhouse is a sight to behold as you drive in – make sure to take a tour!

5 / 6
Sleepy Hollow (Upper)
May 25, 2016


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This course is fantastic. Make no mistake I have played a lot of good courses but this is certainly my favourite but you WILL have a problem getting on. I was very lucky and have managed to play 3 times on weekdays when there was hardly anyone there and I had the time of life!The facilities are excellent aswell including food and practice facilities.Enjoy!
6 / 6
Sleepy Hollow (Upper)
January 05, 2012


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My post from April 2007 indicated that Sleepy Hollow had begun a program of thinning some trees and working on a couple of holes. The result was more than that. Architects George Bahto and Gil Hanse have brought the course back to a consistent vision that would make C.B. MacDonald proud. They have photos in the locker room of what the par 3 16th hole has looked like over the years. It is now back to the original version of itself. On many holes the fairways that had become too tight as the result of 90 years of tree growth have been opened and the new bunkering is perfect. A bonus of the tree removal program has been to open up vistas to the majestic Hudson River. Sleepy is one of the finest courses in the New York metro area. Perhaps Bahto and Hanse should be given a credit in the course details above.
6 / 6
Sleepy Hollow (Upper)
December 06, 2009


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I recently played the front nine of this course in a high school match. Going into the round I had heard good things, but frankly I was blown away when I played the course in person. The April weather was cold and it rained off-and-on, but the experience was marvelous nonetheless. The par 3 third hole is an exquisite test, playing as a mid-iron uphill over a ravine, which you have to cross using a rickety bridge. The par 4 fifth hole also stuck out, as if you carry the hill down the middle of the fairway, you should have a short-iron approach to a truly stunning green complex, complete with a fantastic view of the Hudson River behind the green. The par 3 eighth is also fantastic, as it is a long downhill par 3 with a huge fairway slope that can kick a leftward-bound ball right onto the green. The nine holes that I played of this course are both stunning and stern, a remarkable combination for a golf course.
6 / 6
Sleepy Hollow (Upper)
May 16, 2009


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I grew up in the village of Sleepy Hollow, about a mile from the club but never had a chance to play it until recent years. The focus of attention as you proceed up the driveway is the large, beautiful and ornate clubhouse that sits on top of a hill overlooking the Hudson River. The course is wooded with several very tight tree-lined fairways. There are many elevation changes with an equal number of uphill and downhill holes. On a number of holes its hard to find a level lie so ball position is crucial on your tee shots. They are in the midst of a program of thinning some of the trees and re-designing a couple of holes. The course has a great finishing stretch. The signature hole is the 150 yard par three16th that overlooks the Hudson. It is followed by the downhill 450 yard 17th and the uphill 18th (pictured on this page) with a tricky elevated green that can barely be seen if you approach form the lower right.
5 / 6
Sleepy Hollow (Upper)
April 08, 2007


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