The NYC Recap Part 2 – Sleepy Hollow

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“Anticipation has a habit to set you up for disappointment,” warns Alex Turner, the lead singer of the Arctic Monkeys, in the opening line of their first record. I wouldn’t go so far as to say that Sleepy Hollow was an outright disappointment for me, but, perhaps, more so a victim of the circumstances. Ultimately, I don’t think anything is rated or reviewed in a vacuum; after-all, whether in criticism of art or architecture, there is a human element to the practice which can never be entirely eliminated.

Thanks to Gil Hanse’s and George Bahto’s renovation, Sleepy has gone from being a rather obscure C.B. Macdonald, by way of A.W Tillinghast, by way of Rees Jones, design to one of the foremost classic clubs in the North-East, if not the country. I doubt that any other club’s reputation has benefited as greatly from social media—seriously, is there a day that goes by without someone posting a picture of the course, usually of the 16th hole, on their account? And one cannot deny its beauty, with the Hudson Valley in the background, and the square, thumb-printed green with the bunker that wraps all around it.

The benefit has been a rocket-like ascension up the rankings: it debuted 96th in the U.S. in 2017 according to, and then climbed to 36th in their 2020 ranking; meanwhile, Golfweek (being, as usual, ahead of the curve) ranked it for the first time as the 57th best classic course in 2012, and now rank it 44th. Looking at Golf Magazine’s list, I would probably have it ranked somewhere between its two positionings. And herein lies the crux of my issue, I think: I carried to the first tee an expectation to be playing the 36th best course in the U.S., and I was ultimately let down a tad. 

It also had the unfortunate luck of following Piping Rock, which I would consider perhaps not the best course I have played to date, but likely my favorite. 

The view of the clubhouse from the range

One thing that did not let me down, however, was the clubhouse, an opulent, seven or eight story estate of mustard yellow-hued stone and gray marble that was built by a member of the Vanderbuilt family and was once owned by Frank Rockefeler. Like Piping, Sleepy’s blood runs blue, deep blue. Their website indicates that the club was founded by John Jacob Astor IV, Cornelius Vanderbilt III, and Edward Julius Berwind, among others. Yet, despite this, Sleepy feels rather nouveau-riche, as if, like the remnants of Rees Jones’ work that were swept away in Hanse’s and Bahto’s renovation, that patrician atmosphere which usually pervades turn-of-the-century works built by these American tycoons, and their friends, has been swept away in a onslaught of cell-phone bearing traders and money councillors hoping to get a quick round in before rushing southward into town. Whereas Piping felt quiet, laid back, and sumptuously relaxed, Sleepy, conversely, felt hectic, frenzied, and, well, decidedly un-Sleepy, a Wall-Street trading floor rather than a country estate.

And this frantic sense extends to the golf course, itself. From the first tee shot, which is set literally under the shadow of the clubhouse, to the eighteen green, which likewise finishes at the base of the stonewall under the patio, it is a thrilling, roller coaster ride, climbing up and down, and back up and back down, and back up and back down the massive ridge that bisects the property. I don’t think anyone would evaluate this a great property over which to route a course, but it certainly allowed for some hair-raising, spine-tingling moments, as well as a couple regrettable ones. Here I am referring to the 2nd, a short-ish par 4 that climbs right up the ridge to a semi-blind green protected by a cavernous bunker to its front and right. My playing partner that morning, a Golf Digest rater, found himself in it and I am not sure if he has yet escaped it. The second regrettable moment, and the worst, comes at the 6th, a short, almost cape like par 5. The golfer’s tee ball must climb a mounded, nearly vertical ridge of some fifty-ish feet atop which the fairway is set at a nearly ninety-degree angle. What makes the hole especially difficult, and awkward, for the longer player, especially, is that the fairway is extremely slender in depth, making it nearly impossible to hold when downwind and firm, as it was that day when each member of our three some found their ball resting in the fescue through the landing zone. For the shorter hitter, on the other hand, if he cannot fly his tee-ball to the top, then he is faced with either an entirely blind second from the base of the plateau, or an extremely sidehill one from the rough. However, I’d have to play it a few more times, and in different conditions, to truly judge its merit, but my initial impression of it wasn’t favourable. Perhaps extending the fairway, or banking it in, would improve the tee shot, for, after that, the approach and green are both excellent, in truth. I am especially fond of how they set the “principal’s nose” bunker complex some sixty yards short of the green, mainly as a visual obstruction. 

The scary 3rd, an “eden” template

However, the ill taste was quickly washed away by the plunging, reverse-redan 7th, the best par 3 on the property. The 8th, however, a “road” template, is a bit of a let-down, mainly because it plays straight from the tee, thus eliminating much of the template’s strategic genius. Piping’s “road” hole, on the other hand, is widely considered the best copy of the original, and once again, I think, Sleepy suffered from the circumstance. Although not the most picturesque of stretches on the course—apart from the 10th perhaps—, Sleepy’s middle portion is rock solid, chock-full of tough, interesting golf over rolling, though less extreme, land. The par 5 12th, featuring a creek that must be avoided from both the tee and upon approach, is a real standout. 

The best hole is the 15th, a 505 yard par 4 with a punch bowl green set just over the apex of the main ridge. Setting wise, I doubt that any other “punchbowl” can match it. I also think, considering modern equipment, that the template works especially well at such a brutish length, because it necessitates the golfer to consider where and how to land his second, rather than just fly it all the way to the middle of the green, as he would with a short iron second. That morning, the hole played right into the wind, and I was forced to hit a 3 wood approach, which must have just barely flew the bunker guarding the front of the punchbowl, yet, according to the group ahead, trundled off the flagstick some thirty yards further and settled to an inch.  

The punchbowl 15th in the foreground, with the 16th green in the background

My meager words can hardly do justice to the beauty of the 16th; however, I will say that the thumbprints are far more extreme than I had expected them to be. Considering that the tee ball is played with hardly more than a wedge, I think that the vicious contouring of the green works perfectly. The hole was cut in the far left portion of the green and my playing partner pushed his tee shot well right, leaving him a putt through the entirety of the print, which he failed to property judge and rolled into the bunker.

The now world-famous 16th

The 17th, which tumbles down the side of the main ridge, is a bad hole, feeling somewhat out of place and forced into the routing. Once again, though, the climbing and meaty 18th quickly puts this weaker hole out of mind.

The ultimate approach

The major overriding gripe I have with the routing is that too often the back tees require the golfer to march forty or fifty yards in one direction from the previous green and then retrace his steps to get to the fairway. But I can hardly blame the club for wanting to keep up with the Jones in this respect. The ball goes too far, we all know this.

Deeming a course as the 36th best in the U.S. means that it rests comfortably among the elite. I’m not sure I can quite rank Sleepy that highly, but it’s pretty close for me, likely around the midway point of the list.



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