Sleepy Hollow Country Club

6,630 yards, 136 from the Blues

The life of a golf course. They are conceived, that idea then carried and spoken to others until developed into some kind of reality, at which point the business of building them is set in place. They grow, and those who play them grow fond or perhaps even resentful of them all as time wears on. They change. I am convinced they have moods and their likes and dislikes, just like anything else. They evolve. This evolution comes from the natural landscape upon which they rest, as well as the members and committees and architects and the rest who give their take, whether asked for or not. Holes change. Clubhouses burn. Land gets acquired, or sold off. Trees.

Perception co-exists within this spectrum of course evolution. Rare is the course that is deemed special from the first day and remains that way until the end of time. In fact, there may not be one. They all change and the opinions along with them. Many times, a course is changed to change its perception. To bring it more acclaim and attention, or whatever. Courses certainly do not change on purpose so that those think less of it. Mostly, however, change is brought about in the never-ending journey to make the course better. Yes, the road to hell is paved with good intentions but some times, every now and then, once in a while, they get it right. For a while. For a while. Those might be the most three important words I can think of when it comes to golf course architecture.

We are in the midst of Sleepy Hollow getting it right. Consider in 2008, the course was no where to be found on Golfweek’s top 100 Classic list. It now sits at 44, getting as high as 42 last year. It was also 59 in 2015, showing its climb within the last decade. Rankings are only one of several indicators of course perception. Take a gander at a Golf Club Atlas discussion from the early 2000’s and see what courses are mentioned and how. Look at golf magazines from the prior two decades and see how many “must plays” have fallen out of favor. Sleepy opened in 1913. In its lifetime of over a century, perception of it is at one of its peaks for the last ten years. Mind you, this is popular opinion, social media and the like. Sleepy Hollow has enjoyed its magnificent terrain and the fairways upon it which rise and fall for decades upon decades. There are those that have walked amongst it for years and simply entrusted its change to the right people, who brought out a superb rendition of it for this point in time. We all hope that bloom continues forever more.

While a course at the height of its powers and popular opinion occasionally do not coincide, I am fine stating the accolades recently bestowed upon Sleepy are rightly deserved. While I was intrigued the first couple holes, what grabbed my serious attention was the Eden hole at the Third. A ravenous chasm between tee and green as the green is set on a hillside above and the bunkers front and right giving a taste of the depths the chasm can get. It really didn’t end after that; the Eden gets you up the ridge, which opens up the hills and meadows that most of the course is placed. Several renditions of the template holes are impressive, which yes, includes the Sixteenth Short. I was equally impressed, however, with the fairway shaping, which likely does more for strategic interest than the greens. While I was surprised not find a Hog’s Back, or at least a hole named after it, I started to realize there were aspects of the old hog in several of the holes. There were areas of preference and disfavor that the golfer would not immediately realize until getting to know the course better. No, he would simply stripe his tee shot and think that is that. It would not be until he reached his ball and surveyed his approach options that his fortune or misfortune comes out of the ether. The setting and terrain are grand, which goes in hand in hand with the playing structure, both feeding off the other symbiotically. Deftness about the greens is a prized trait in playing well here, as mounds, precarious lies and greens running in haphazard directions must all be accounted for. The height of its powers, indeed. And while it certainly played as if it had been here all along, Sleepy is a prime example of course evolution finding its stride at the right time with the right people bringing about that change.

Indeed, Sleepy is not an example of a course that shined with exuberance before the work of modern golf designers some how ruining it, which was then saved and redeemed. The course is on dramatic terrain and while Macdonald initially did well by the course, disagreements with Rockefeller over tree removal disinterested him on the site and it was still early on in Raynor’s career for him to shoulder the load alone. Subsequent land transactions and work by Tillinghast and a local architect named Tom Winton further changed the course, whose club sought coherency in the late Twentieth century. Rees Jones then came in and working with the club, a modern rendition of the course was born. While some enjoy bemoaning Rees’ work here, they fail to consider the historical context within which the work was performed. Templates, Raynor and restorations had yet to achieve their trendy place in course architecture. It’s also not as if Rees did his work overnight without extensive consultation and oversight. 

Almost two decades after Rees’ project, the club sought another direction with the course. Gil Hanse and the late George Bahto were retained to transform the course into a cohesive Macdonald design. Not restore what was there at some point, but instead to re-design the course with Macdonald design principles as the guide. This work took place in 2006 – 07. The greens were then worked on about ten years later. At long last, the course is a brilliant rendition of MacRaynor on sharp rocky terrain boasting awe inspiring views of the Hudson. The fairway shaping keeps up with the marvelous greens, making for a memorable play that surpasses anything it was prior to Hanse and Bahto initially setting foot on the grounds. It is said Bahto would walk the fairways for hours, carefully crafting their intricacies and configurations to the greens. This certainly comes through as the golfer walks down the very same fairways.

Admittedly, I had Sleepy fatigue before I set foot on the property. Its camera friendly holes with their sharp, bold templates and scenic setting along with a supreme course name and insignia of the headless horseman led to a meteoric rise in popularity on social media and course design circles. My twitter feed was one photo of the Sixteenth Short after another, at sun rise, sunset, the sun itself putting for par, etc. etc. Everyone I spoke to about the course had effusive praise, insisting I play it and almost offering to drive me to the course post haste. Don’t get me wrong, that type of acclaim is a good thing, but I did start to wonder if all the hype would lead to a let down once I was able to get there. Yet, there was no let down. In fact, I realized there was much much more beyond that dreamy, heavenly Sixteenth.

And yes, I will drive anyone there who has not yet played it, post haste.

The First is a 418 yard par 4 (from the Blues). “Leven.” Heading out innocently enough from the clubhouse, the fairway bends ever so gently to the right while its right to left cant is enough to influence the ball several paces in that direction upon landing. Beyond the bend is the green, almost blending in to the wide open expanse at the approach. Each bunker on either side of the fairway leading up to the green intrudes into the fairway, which swerves around it and creates an impression of more twists and turns than are actually there. Bunkers line each side of the green but the configuration of the mounds complicates the ground game and putting in a very good way, ensuring the golfer must study things before deciding on a line.

The First
Approach shot territory
A bit closer
The green

The Second is a 332 yard par 4. “Climbing.” One may wonder where the rest of the golf course is after finishing the First and the answer is, “up and over.” This hole indeed climbs the sharp ridge that leads to the majority of the holes. The two bunkers in the middle of the fairway look benign but it just takes a little miss, or even a slight misjudgment in distance, to end up in them. Most should have a shorter blind approach up the hill and on to the green but there are fairway bunkers off to the sides closer to the green that menace matters.

The Second
Moving up the fairway (the large flag is for the Fifteenth green)
Approach shot territory
Off to the right, the golf course is on the the other side of the ridge
The green

Some of the views upon reaching this terrace:

The Third is a 172 yard par 3. “Eden.” An extraordinary canvas for a par 3 in general let alone an Eden, the green seems to float before you at the tee. The strath or shelly bunker; I believe it’s a bit too close to the green to be a shelly, is the only bunker we can see from the tee with the rest hiding. That includes the deep right side and the mischievous one on the left. The green is well defended as it shows off its tremendous good looks.

The Third
Take the bridge, which fits in nicely with the character of the club
From the left

The Fourth is a 415 yard par 4. “Headless Horseman.” Heading to the interior of the course, the downhill tee shot is generally blind with only a fairway bunker on the right and right to left tilt to contend with. The approach is a lot more interesting, with the green and that of the Fifteenth some what connected together and bunkering short left, then on both sides of the green. Deceptive. The green is large yet it always seems as if the bunkers or contours get in the way of the golfer using it all to his full advantage.

The Fourth
View from behind the tees
Moving down the fairway
Approach shot territory

The Fifth is a 435 yard par 4. “Panorama.” We are not done with that ridge just yet as it is too remarkable of a geographical feature not to use as much as possible. The tee shot climbs back up the hill. I noticed a spring in all our steps as we bounded towards the crest, knowing the views that awaited. It does not disappoint. The right to left cant of the fairway and larger bunkering leading up to the green make the approach towards the Hudson challenging yet invigorating. The approach is likely longer, so all of the bunkers and contours come into play more often than it initially appears.

Fairway of the Fifth
The green and glorious Hudson in sight
Approach shot territory and final climb to the green
The green
Looking back

The Sixth is a 475 yard par 5. “Lookout.” We finally move from the immediate ridge area to a nearby hillside before getting into the lower meadowlands. Sharing the fairway with the hole prior and the Eden green paces away to the right, the tee shot is free to venture as far left as you’d like but anything to the right will be devoured by the trees. It may seem we continue off to the left but no, we are headed off to the steeper and more severe right side. The second shot will need to get up and over the hill, at which point the rest of the fairway and green are revealed. One thing the course is the reveals. The power of the visuals that hit the golfer all at once is certainly good for the soul. There are mounds and bunkers that comprise approach shot territory, including the principal’s nose, and the green hides among them. It reminded me a little of the approach at the Eleventh at Pine Valley.

The Sixth
Moving up the fairway
Up the hill, the green is straight out in the distance, a mesh of mounds and bunkers mars the path to it
Closer, and what appears to be a Principal’s Nose
Short approach shot territory
The green and its entry point

The Seventh is a 221 yard par 3. “Redan.” The course is now in full stride as its character shines. A drop shot Redan nonetheless with the hillside on the left obstructing a complete view of the green. The angle and elevation from the tee puts the lower left bunker a lot more in play than most Redans, which in turn puts the right bunker a lot more in play. It is certainly a well fortified green yet there is plenty of it in size and the hillside masks the fantastic side board before the green on the left that can be used to bounce and roll the ball on. A great par 3.

The Seventh
The green
Looking back

The Eighth is a 460 yard par 4. “Road.” This lower land runs out and back, which is full of all kinds of intricate shaping and contouring that fits in well with the landscape. Well removed from the sharp hills that comprised most of the course thus far, this flatter terrain and how it is used showcases even more layers and personalities to the course. The tee shot is out into it, the stronger right to left movement not immediately evident. The fairway then narrows after tee shot territory, which is evident where the bunker on the right intrudes. This gets us to the green. The front left is guarded by a deep bunker, which of course should be avoided at all costs. I suppose the cart path serves as the road, outlining the rear and rear right of the green yet serves it purpose as it is no where the golfer would like to be, especially with the green running away from him towards said treacherous bunker. It’s a marvelous green and approach, coming at the right time and leaving the golfer no excuses of not being “warmed up.”

The Eighth
Moving down the fairway
From the left
Approach shot territory
The green

The Ninth is a 382 yard par 4. “Knoll.” Still heading in the same direction, the fairway is inviting enough yet is important to hit anyways because of the approach shot after it. There is indeed a knoll before the green that must be carrier while bunkers line both sides of the green.

The Ninth
The treacherous fairway
Looking back
Approach shot territory
The green

The front nine gets us to the far point of the course and flashes its steeper ridges before mellowing out at the close. The par 3’s and 5 exemplifies the variety and interest here while the par 4’s have nice range and the greens are extraordinary in their shaping and interaction with the terrain. I would rank them 3, 7, 6, 8, 9, 2, 5, 4, 1.

The back nine starts with the 168 yard par 3 Tenth. “Lake.” Nestled at the far corner of the property, the lake separates us from the green. It must be carried, while a spine runs through the middle of the green and slides balls away from the center. It’s a serene moment in the round.

The Tenth
The green
Looking back

The Eleventh is a 407 yard par 4. “Ichabod’s Elbow.” We now start heading back to the ridge. A slight dog right made even more so with the tees place to the right of the fairway. The green is above the fairway after the turn, its entry point ramping up while greens are on either side, perilously below.

The Eleventh
Approach shot territory
Closer
The green
The green, from afar

The Twelfth is a 536 yard par 5. “Double Plateau.” A dog leg left where decisions off the tee need to be made. Hugging the left side means being closer to the green and either setting up a more manageable approach or going for the green altogether while the right side off the tee is safer, yet means more distance coming in. A creek, or dry creek as it is, runs diagonally across the fairway, separating it in two. The green is devilish, narrowing at the rear and falling off steeply on all sides, all with a bunker on the high right side. And of course, the green includes not one, but two, plateaus. Such interesting approach lines coming in to this green, the hole is very good.

The Twelfth
Moving down the fairway
Looking back
Approach shot territory
The green
More looking back

The Thirteenth is a 398 yard par 4. “Sleepy Hollow.” A detour to the ridge as we branch up the wooded hills the next couple holes. The tee shot is uphill while bunkers lurk on the left side, with one being so bold as to cut into the center of the fairway. The fairway is uphill to the green, with pot bunker at the front and center of the green. There is run off where the tee for Fourteenth is on the left while the right side is all bunker.

The Thirteenth
Moving down the fairway
Approach shot territory
The green

The Fourteenth is a 380 yard par 4. “Spines.” Coming off the hilltop and back towards the direction of the ridge, the bunkers take a cue from the hole prior and impede towards the center line, first right, then left. The fairway tilts and swales, then funnels to the green, all of it mostly downhill. Terrain movement is prevalent here and needs to be minded on each shot, or can be used to the golfer’s advantage, especially near the green. There are indeed spines running through the green, at an angle and more towards the center. They certainly complicate putting from one side of the green to the other but I enjoyed their additional character, impressing the importance of getting the approach right in the first place.

The Fourteenth
Moving down the fairway
Approach shot territory
The green, with the spine noticeable
There’s one spine
The grade leading to the bunker

The Fifteenth is a 457 yard par 4. “Punchbowl.” Many marvel at how punchbowls enhance the ground game, watching the ball rolling round and hopefully making its way closer to the hole. Like Fishers, the approach is blind so whatever happens to the ball upon landing in the bowl is a mystery. The green is below the fairway, the land leading up to it swerving around assorted bunkers on the sides. I must say, hitting the approach into the great unknown with the Hudson and sky beyond as the backdrop makes for an exhilarating shot. The bowl has a dominant left to right movement while back side won’t stop the more furious approach shots bulldozing their way in so take heed on that front.

The Fifteenth
Moving down the fairway
Approach shot territory
The punchbowl

The Sixteenth is a 149 yard par 3. “Short.” There is simply no doubt that this is a special hole. The template itself is standard, with a narrower bunker wrapping itself around most of the green while the green itself is more rectangular than round. I fell in love with the template ever since I stumbled upon it at Yale over a decade ago. The tee shot is head to the green and the same ravine we had to carry at the Third is in play here. The view is spectacular with one of the more picturesque backgrounds to take in. The right to left movement of the hillside along with the interior contours of the green, however, are what surprisingly impressed me the most about the hole. This makes it infinitely more challenging, especially for those who miss the green. And particularly for those who miss the green on the higher right side.

Every now and then, my game elevates in appreciation of the design before me and this was one of those occasions. I hit my tee shot to 10 feet of the pin in the right place and was able to walk away with a very satisfying par.

The Sixteenth
Obligatory photo at the tee

The Seventeenth is a 446 yard par 4. “Hudson.” Our work on the ridge coming to an end, we now head back over the other side, the tee shot using its severe left to right movement wonderfully. This almost makes the stated yardage irrelevant, as most tee shots will roll significantly down the hill and inevitably closer to the green. The golfer may notice a fairway and green leading off to the right. That is not our Eighteenth, but rather there are a separate nine holes designed by Tillinghast in the 1920’s that utilizes the lower part of the hillside, nearest the Hudson. In addition to the additional nine holes, Tillinghast worked on the Eighth through Eleventh, his style captured as part of the most recent restoration. Those nine holes are for another trip here but as for this hole, the green is a natural extension of the downhill fairway with a nice and wide entry point, welcoming approaches that are bounding and bouncing down the hill.

The Seventeenth
Approach shot territory
Short approach
Looking back

The Eighteenth is a 426 yard par 4. “Woodlea.” The hole is named after the clubhouse, which is perched prominently above us, the end point of our journey. The tee shot is uphill towards it, the hillside moving left to right and bringing that large tree into play more often than it may look at first glance. The fairway narrows after that tree and that left to right movement becomes even stronger as we near the green. The clink of plates and idle chatter make their way to the green with the clubhouse upon us yet that left to right movement and the contours of the green demand our full attention to the last.

The Eighteenth
Approach shot territory
Closer
The green

The back nine completes the out and back with a couple outstanding par 3’s and 5, as well as another impressive array of different par 4’s relying on the terrain in their own distinct manner. Like the front, it’s very well balanced and there are no weak holes. I would rank them 12, 14, 16, 15, 10, 18, 17, 13, 11.

Generally, Sleepy Hollow demonstrates just how splendid course architecture restoration can influence and improve an existing layout that may not be realizing its potential. A set of circumstances finally fell into place here through careful planning and study, resulting in what is likely the best rendition of the course. The decision to stay as close to Macdonald’s style as possible while crafting the fairways and greens in intricate detail yielded a very strong course that accentuates the exuberant terrain and unlocked its advantages to the game. The course has gained notoriety at a meteoric pace so now even the more casual golfers know of and want to play here among the hills. That is no small feat. Its rise in popularity is rightly so. A wealth of strategy is now within each shot and the greens are joyously complex, ensuring the golfer will learn something new each round. The work at Sleepy should be applauded. Bahto was one of the foremost studies on Macdonald and his involvement here with Gil surely led to a large amount of decisions within the renovation process. As the golfer stands at that Sixteenth tee and looks out to the green and Hudson beyond, he can be sure that some where above in that grand old sky, Bahto is smiling down upon it through and through.

Clubhouse/Pro Shop: Stanford White designed the impressive Victorian structure in the manner of the Italian villa style that was popular at the time. Approximately 75 rooms, including an elaborate ball room and flanking formal gardens, it is worth exploring in detail if possible.

Practice area: The driving range is at the lower front of the property. It feels as if you are warming up in the front yard, in a good way.