Sleepy Hollow Country Club

Sleep Hollow Country Club marked the last round of golf during my time in New York City. The summer of northeast golf ended on a great note. Sleepy Hollow is one of the great under recognized courses in the northeast US. In his book, The Confidential Guide to Golf Courses, Tom Doak refers to Sleepy Hollow as, "Westchester's best unknown golf course." This is quite a compliment considering the quality of courses in Westchester County and Doak's notoriously strong opinions. After playing a handful of great golf courses the summer, Sleepy Hollow easily ranks as one of the most enjoyable rounds that I played.

Famous headless horseman club logo

William Rockefeller built the club for a “who’s-who” of New York businessmen. Over after its creation, the members still hold a special place at the club. I had been told by my host member at Winged Foot, “You are going to love Sleepy Hollow. The course is great, but it is the members who make the place so special. They are all really good people.” His advice held true during my visit to Sleepy Hollow.

The first thing to strike golfers arriving on the property at Sleepy Hollow is the mansion clubhouse. The clubhouse is a spectacular old Vanderbilt estate house, known as “Woodlea”. The clubhouse was completed in 1894, and was sold to Sleepy Hollow Country Club in 1920.

The golf course has an interesting history. Charles Blair Macdonald designed and finished the course in 1911, but its history doesn’t stop there. In the late 1920s, A.W. Tillinghast was brought in to add an additional 9 holes to the club. In so doing, Tillinghast created what are now the first, eighth through twelfth, and eighteenth holes, and then knitted them into Macdonald’s course. It created two different flavors coming from two very different designers.

Over the years, various greens committees, with the help of “name” designers, changed the course in attempts to “modernize” it, achieving lukewarm results. In the mid-2000s, Gil Hanse, with the help of Macdonald expert George Bhato, was brought in to restore the course back to its original Macdonald design. The removal of trees, changes in bunkering, and overall layout alterations resulted in what Golf Club Atlas described as, “...a renovation that represents one of the great transformations in the history of golf course architecture. (Sleepy Hollow) went from a lifeless course that had lost its soul, a ‘new old’ course full of character...”

Hole #1 - 406 yards - "Sunnyside"

The round begins with a downhill par 4 moving to the golfer's right. The elevated tee box at the base of the Vanderbilt mansion provides just enough of a view to whet your appetite for the holes to come.

Hole #3 - 153 yards - "Haunted Bridge"

The par 3 3rd requires a shot over a large gorge. This hole is Macdonald's Eden hole at Sleepy Hollow. Bunkers on the left hillside and low right of the green act as tough penalties for any wayward shots. Click on the picture to enlarge and have a closer look at both the green and the unique bridge across the gorge.

Hole #5 - 403 yards - "High Tor"

The tee shot on the fifth is blind cresting a ridge. The photo above is taken from the top of the ridge. As golfers leave the tee box and proceed up the fairway, the view is breathtaking... Some members called this the most improved hole on the course after Hanse did his work. There were once a large number of trees behind this green, completely obstructing the view of the river. Removing the trees opened up the hole and allowed the gorgeous view to come through.

Hole #6 - 458 yards - "Headless Horseman"

This par 5 is an almost 90 degree dogleg right with the bend on the top of the hill seen in the distance. Short hitters play into the valley and then play a second shot up over the hill. Long hitters can cut the corner and play to the top. Part of the brilliance of this hole is that, despite the short length, it is a three shot hole for those unable to carry the ball over 250 yards. The hole is a great use of the terrain.

The picture above shows the approach to the green once on top of the hill.

Hole #7 - 193 yards - "Tarry Brae"

This downhill reverse Redan hole is one of my favorite par 3s which I have recently played. The green slopes right and away from the tee box. A slope short left kicks ball down and onto the green. My photo doesn't show the green particularly well. I could have sat with a bucket of balls on this tee and happily hit all afternoon.

Hole #9 - 439 yards - "Katrina's Glen"

The 9th hole gives golfers a true taste of AW Tillinghast's input at Sleepy Hollow. Holes 8-11 have a noticeably different feel, yet they still flow well with the rest of the golf course. The 9th is a dogleg right par 4. A shot out to the bunkered corner of the dogleg leaves a very interesting 150 yard approach. The green appears to be open for the taking, but bunkers left and right, along with a sloping front present a challenge. 

Hole #10 - 156 yards - "The Lake"

This par 3 is another one of the course's very picturesque holes. It holds a different kind of beauty from the expansive views of the Hudson seen at other points in the round. The hole plays slightly downhill, and a back left slope acts as a backboard for the safe long, left shot.

Hole #12 - 513 yards - "Double Plateau"

The 12th hole saw the largest change during the Hanse and Bhato renovation process. Over two hundred yards were added to the hole, turning it into a par 5. A completely new green complex was created. A long, straight par 4 was turned into an interesting dog leg left par 5, incorporating a creek on the second shot. The name "Double Plateau" comes from the tough, two tier green. Be sure to make note of the pin placement and/or obey your caddy. I did not, and I payed the price with a double bogey. The changes to this hole also drastically improved course routing, which originally required a very long walk from the 12th green to 13th tee.

Hole #13 - 384 yards - "Andre's Lane"

The severity of the slopes in front of this green are not fully realized in this photo. It is a challenging approach shot to the elevated green. The fairway is also filled with strategically placed fairway bunkers. The green also slopes from back to front. That fact combined with fast green speeds dictates extreme caution when putting from above the hole.

Hole #15 - 437 yards - "Punchbowl"

The 15th hole also saw major changes during the restoration. The hole was changed from a par 5 to a long par 4. Average length golfers would have around 100 yards for their third shot into the punchbowl green. This eliminated use of the strategic slope short left of the green. By moving the tee boxes up and creating a long par 4, Hanse fully capitalized on Macdonald's original design. This was one of my favorite par 4s on the course.

Hole #16 - 150 yards - "Panorama"

"Panorama" is a fitting name for this par 3. The bunkering around the green saw a drastic change during the restoration. Small, cluttered bunkers and mounds guarded this green instead of the wrap-around bunker seen today. After looking at a 1920s photo of the hole in the clubhouse after the round, it is obvious that the current design is the original. Greens committees and various designers had changed the bunkering over the decades.

Hole #18 - 406 yards - "Mansion Rise"

The final hole on the course is fairly easy if played correctly. However, enter a fairway bunker or one of the massive bunkers front right of the green and you will pay a huge price. The hole is framed beautifully by the mansion clubhouse directly behind the green. 

I hope to have the chance to play Sleepy Hollow again. The photos barely do the views and beauty of the course justice. The round presented me with the necessary reminder that golf isn’t only about difficult courses capable of hosting major championships. My round at Sleepy Hollow was fun. It required a huge variety of shots, and each hole had unique character. The clubhouse, the overall aura of the place, and my playing partners all combined with the course to make an extremely enjoyable day.