First Impressions
Upon arriving at the gates, a winding road leads the way up the hill and back in time, placing us at steps of the iconic gilded age mansion that is unmistakably Sleepy Hollow’s. The estate was built in 1893 for $2.5 million, intended to be a private residence for Margaret Shepard, the wife of Colonel Elliott Fitch Shepard and daughter of William Vanderbilt. The mansion passed hands a few times before being purchased at a bargain ($165,000) in 1910 by William Rockefeller and Frank Vanderlip.
Some iconic names in American business history there no doubt, the new owners decided to gather others of similar status and commission an exclusive country club with 600 members in 1911. Initiation and dues were $100 (~$3500 today), if only we were so fortunate to have that opportunity now!
C.B. MacDonald and Seth Raynor were brought in to design the course, and the 2008 renovation from Gil Hanse brought the course back to its former glory with the intent of restoring the era appropriate original Macdonald. The result is breathtaking, and a frequent residency in the world top 100.
There is plenty to take in while exploring the clubhouse inside the mansion, and we’ll let the photos do the talking.
The Course
Design: C.B. Macdonald, Seth Raynor
Year Built: 1911
Yardage: 6902/6630/6340/5682
Rating: 74.6/73.0/71.8/68.1
Accessibility: Private
The Front 9
The opener is docile enough, a 418 yard par 4 with an open fairway that bends slightly to the right and playing from an elevated tee box. The troublesome tree on the right makes itself obvious, but there isn’t a ton of trouble otherwise with the exception of a fairway bunker on the left for longer hitters to contend with.
The green is larger than it appears due to the illusion created from the raised lip before the surface on the right side, the green slopes front to back and left to right. Bunkers lay on both sides of the green, but the hole is a fairly gentle handshake per se.
It doesn’t take long for the drama to get going. The 2nd is just 332 yards, but plays almost directly uphill, more than the pictures can do justice. It is a hole that leads us to the rest of the course above the ridge. The approach will be a blind chip to a challenging green sloped back to front, making our front left pin position exceedingly perilous to the point that even the caddies were surprised.
The 3rd is spectacular and is the first of the best set of par 3s we’ve encountered. Forsgate previously held this title for us but Sleepy Hollow’s one shotters are in a class of their own (although Banks’s work at Forsgate is not to be discounted).
The Eden template is first and you couldn’t ask for a better setting for it.
The hole plays over a valley that frames the hole perfectly. The prominent bunker makes itself known on the right side of the green and juts out a bit into it, but a reticent bunker minds its business on the left as well. A beautiful par 3 that is aesthetically pleasing as it is complex.
While the hole is world class, it is difficult to fully pay attention to it at first as one of golf’s great bridges is to the left. A signature of Sleepy Hollow, it was amazing to see it in person. I don’t know how it stands, but our caddy said it fended off a devastating storm that took out over 150 trees on the property, so it is clearly assembled with precision.
We’re now over the ridge and headed to the belly of the course. A par 4 measuring 415 yards awaits with only a fairway bunker on the right representing trouble. The tee shot is downhill and doesn’t offer much danger.
The approach is far more compelling, bunkers on the left side prevent the ground game from coming into play, and the angle from the right side of the fairway is diagonal. A bunker guards the right side and the 15th green looks almost connected on the left with yet another bunker hugging the green.
The 5th is another standout in a lineup of many. The tee shot is blind over the ridge, setting the stage for the namesake of the hole, “Panorama”.
The reveal doesn’t disappoint.
An infinity green dazzles on the horizon with the Hudson, framed by a right to left slanted fairway and a trifecta of fairway bunkers that jut out just enough to be a nuisance. The hole plays a bit long at 435 yards and uphill off the tee, so the variety of trouble that persists around the green is likely to assert itself frequently. A magnificent par 4.
An unveiling awaits us at the 6th as well, a par 5 whose danger off the tee is obvious.
The 5th fairway provides refuge on the left as the tee shot takes us over a valley and back up the hill as we approach the next portion of the course.
As we crest the hill, another dose of eye candy hits in the form of countless monds and bunkers including the renowned Principal’s nose. Just enough to the eye to make one second guess aggression.
The world class quartet of par 3s is back for its next act for the 7th, the 221 yard Redan.
Playing from high above to the diagonal angled green, this is as unique a par 3 as we’ve played. While the hillside blocks some view of the left from the tee box, there is a hill that feeds directly to the green which makes this hole a blast. My tee shot was pulled to about the leftmost tree. I thought my shot was dead until our caddies let us know to watch in marvel and getting my heart rate through the roof saying “that’s a 1”. Slowly but surely, my ball rolled to about a foot away, excruciating but unforgettable and a testament to how fun the hole is.
As the adrenaline from the near ace lingered, I had to refocus as the journey reached the 8th. A very stern par 4 and the #1 handicap on the course, it’s the Road template and plays 460 yards. This is the first of the sequence of holes that plays on flatter ground on the interior of the property, highlighting Macdonald’s prowess in adding character to less dramatic terrain. The fairway slopes right to left and there are plenty of ways to get in trouble off the tee.
A lengthy approach likely awaits most players, and the fairway is trimmed in width as we reach approach territory. A large bunker defends the left side of the green, and is the most dangerous hazard to consider.
The 9th is the “Knoll” template checking in at 382 yards. Trees hug the right side of the hole throughout, with a fairway bunker adding additional danger on that side. The fairway is inviting and clubbing down is the prudent play, but the fairway runs deceptively uphill before approaching the green.
Bunkers guard both sides of the familiar square shaped Macdonald green.
The front nine is a journey up and over the defining ridge where much of the back nine is found, and is full of character. I’d rate them 7,3,5,4,2,9,8,1,6, but I’m nitpicking.
The Back 9
The back wastes no time getting going, with another excellent par 3.
Tucked away in the back of the property, the 168 yard par 3 10th brings water into play for the only time in the round. In moment of foreshadowing of the 14th, a spine asserts itself in the green making any tee shots that land on the wrong side of it for the day punished in the form of a legitimate challenge to save par.
Beginning our journey back towards the water, the 11th is a par 4 that plays to a diagonal fairway out to the right. The tee shot is simple enough, but the challenge lies in the approach to a severely elevated green with deep bunkers guarding the circumference of the surface. Difficult approach shots to elevated surfaces assert themselves as the back 9 progresses.
Our host’s favorite hole on the course, the final (of only 2) par 5s on the course awaits as the 12th. Playing 536 yards and a dog leg left, the hole is a test of risk tolerance off the tee, challenging trees and waste area to cut off distance is alluring while there’s plenty of room out to the right at the expense of a longer approach in. A creek bisects the fairway as we approach the green.
The green is elevated, making going for it in 2 difficult and requiring a great long iron or wood shot. This hole certainly had Tillanghast influence to it and is a fun yet demanding par 5.
A nifty par 4 is tucked away into the woods for the 13th, playing 398 yards and uphill. Bunkers are hidden by the ridge up the left side of the fairway but are happy to boisterously reveal themselves on your walk up the hill.
A deep pot bunker is placed in the climb up to the green with another bunker guarding the right of the putting surface.
The course starts to pick up intensity from here and a remarkable finishing stretch begins. The 14th is named “Spines” and is a 380 yard par 4. There’s a lot of digest off the tee, and the contours of the fairway mean the adventure is only beginning when your tee shot lands.
Length isn’t the issue here as the hole play primarily downhill, but bunkers intrude from both the right and left sides. I reckon the placement of these bunkers make them particularly frequented.
While tee to green is interesting enough, the green is the star of the show on this hole, with 2 unique spines running parallel to one another providing distinct character. I’ve never seen a Macdonald green with this feature and I can imagine many adventurous putts on this surface.
The 15th is next, now this is a par 4 to remember. Bunkers are laid out in a similar cadence to the previous hole but there is more room to operate as they shouldn’t come into play often. The hole plays 457 yards so grip it and rip it.
The genius in the hole lies in the approach, an exhilarating shot to a blind green that lays below the fairway. The white flag in the picture above represents the target line, allowing a level of optimism or pleading the golf gods for grace as your ball disappears into the horizon.
The reveal is stunning, a Fishers Island-esque punch bowl green with the venerable 16th looming to the left. The green is tilted left to right and is a blast, I could chip balls down the slope and watch nature take its course all day. What a fun hole.
The next is a hole that doesn’t need an introduction and is perhaps most responsible for the meteoric rise in popularity of Sleepy Hollow recently, the 149 yard “Short” par 3 16th.
An iconic hole, with features abound including a square thumbprint green, a moat like bunker surrounding it, and a spectacular view of the Hudson. It is without question a bucket list hole, and one that had the jitters going over the ball on the tee box. Fortunately Shayne and I both hit great tee shots, but the greenskeeper must’ve been looking for a laugh on this day as the pin was in a diabolical position. The green is deceptively challenging, sloped right to left with several intricate contours that make the hole have more teeth than you’d expect.
This hole is one of the best examples of restoration and a stroke of genius from Gil Hanse, have a look at the before and after from LinksGems.
Without a doubt one of our bucket list holes, it certainly is one we took a moment to really take in and feel fortunate to be in front of, a reminder of why we love the chase of the game and the best courses in the world.
Following the special 16th, the penultimate hole has big shoes to fill, and it delivers with more fun with driver in hand.
The 446 yard par 4 17th plays much shorter as the ridge bids us farewell with a gift, a tee shot that plays severely downhill and helped further by the left to right slanted fairway. The green is welcoming as well, with bunkers residing on both sides. This is a fun and generous hole that should allow plenty of birdie opportunities with execution off the tee.
Macdonald’s generosity ran out when designing the 18th, but a final postcard level view is the reward for our troubles. The Vanderbilt mansion is framed perfectly and looms large, it’s a spectacular setting fo a finishing hole.
The hole itself is demanding, a 426 yard par 4 that plays uphill with a fairway slanted left to right, making the imposing tree on the right a factor. The severity of the bank both up and right increases as we march up to the green.
The green is flanked by a perilous bunker on the right side, one of the deepest on the course. Any approach taking the ground route will almost assuredly find itself in this crater of a bunker. The patio and clubhouse nearly hug the green, providing an alluring backdrop to the festivities.
While the back takes a few holes to get going (relatively speaking), the finishing stretch is special and one that will be stuck in our minds forever. The feeling looking out over the horizon on the 16th tee is unforgettable, one of several truly memorable moments this course produces. I’d rank the back 9: 15,16,18,10,12,14,17,11,13.
Final Thoughts
What else is there to say? We feel truly fortunate to have checked off this bucket list course so early in our journey, and are so happy it lived up the sky high expectations we had for it. The experience is world class from start to finish, made even better by our terrific host who we are extremely grateful for. The future for the club is undoubtedly prosperous, and it is a place we are clamoring to return to as many times as we can. If you receive the chance to play, drop everything and travel as far as it takes to make it happen, an exhilarating journey awaits.
Pros
-Historic golden age layout and a masterclass in restoration
-Perfect conditions, views, and experience
-World class amenities and pro shop, a top logo in golf as well
Cons
-None
Favorite Holes
So many options here, but 7, 15, and 16 have stayed in our heads. An argument can be made for many of the holes though.
What Would We Pay?
This is relative to everyone’s budgets, but I don’t think you’d walk off the 18th green disappointed at any number that is comfortable to you. Certainly more than any of the premiums that high end public golf is demanding these days. It’s a one of a kind round and a truly special place.
Final Score
9.5
See how we score here