Sleepy Hollow (Upper) - New York - USA

Pictures really don't do it justice. 16 gets the fame but 15 was a better hole in my opinion.

Sleepy Hollow lies high above the Hudson on the Vanderbilt estate. While playing the course was undoubtedly one of the coolest things I've ever done, the most fascinating part of the day was finding in the Sleepy Hollow cemetery the headstone of my great great grandfather, an Irish immigrant whose first job was as a groundskeeper on the property.

The ground which my great great grandfather once maintained has been touched by the likes of CB MacDonald and AW Tillinghast. The course has changed a lot with different land acquisitions and architectural trends, but it has luckily been brought back to life after Gil Hanse removed the wreck that R*es Jones made.

The starter is a leven template, with the classic bunker in the front and sloping green. The shaper was instructed by Hanse to visit Chicago Golf Club in order to study the fifth green, another leven, which he said he looked at for days in awe. The second is a hole that serves a purpose of getting up the hill. Its an interesting hole with a cool green site that yields the first view of the Hudson. The third plays across the ravine to an eden green. Members originally wanted a Biarritz here akin to nine at Yale, but Hanse insisted on the eden as the Biarritz would not fit the landscape. He was definitely right, creating a great one shot hole.

Four is the first introduction of the Tillinghast influence in the course. While most of the current routing mimics Tillinghast's work, Hanse and the membership opted to create template holes instead. However, the fourth is a great green that would fit right in at Winged Foot, making for a great hole. Five is an awesome semi-blind tee shot playing over a ridge into a crevice, from where the second shot plays to an undulating infinity green with the Hudson on the horizon.

As someone who has played a few rounds with hickory sticks, I have absolutely no idea how people played the fifth hole back in the day. You have to carry a massive ridge that diagonally bisects the fairway, making sure you don't bail out and end up blocked out by a tree. The second is played over a principal's nose bunker to a raised green.

Seven is the most natural version of the Redan I've seen - carved into the hillside with a natural kicker that you have to use to keep the ball on the green. Eight is the first trip into the woods where the fairway features a massive hogs back to reinforce strategy. The second is played up to a green mimicking 17 at St. Andrew's. Nine is a great dogleg right around the hill played up to a maiden/knoll style green, completing the first leg of Sleepy Hollow's true out and back routing.

I usually hate water and better yet par threes with greens butting up to water, as they usually remind me of boring Florida or Jones golf. I can make an exception for the 10th, as its honestly one of my favorite par threes. Its not overly long, a mid iron at most, and plays to a green with a massive ridge in it, rewarding the player that plays closer to the water as it funnels balls to the hole, but penalizing conservative players with a long treacherous putt.

11 is Ichibod's Elbow, one of the hardest holes on the course. It doglegs right between two massive rock outcroppings, playing straight uphill to an L shaped green. 12 is a completely new hole, but Hanse did an excellent job with it. It plays somewhat like AGNC 13, a dogleg left par three where hugging the creek on the interior yields a good look at getting home in two. The green is a raised double plateau. If you look way up the hill to the right, you can see the former greensite, which was originally encroached by trees making one of the stupidest holes in golf.

13 is probably the most underrated hole on the course, as it reminds me a lot of 10 at Shinnecock. The tee shot plays down into a valley with a second shot up to a high, sloping green. Missing short could cause your ball to roll all the way back to your feet, which my dad learned the hard way. 14 features another MacDonald inspired green which Hanse put in that is extremely awesome to play. Its an extremely severe version of the hog's back 9th at Chicago, with two massive spines demanding accuracy on the approach.

15 is an alps/punchbowl hole that is a true par 4.5. Playing towards the Hudson, the second shot is played over the ridge down to a blind green. Pure excitement follows as you walk down to the green seeing the massive bowled green and seeing where your ball will wind up. 16 is the hole you've probably seen a million times on LinksGems. We were lucky enough to play it right at sunset, with the crimson rays bouncing off the Hudson. The green is a perfectly restored thumbprint green. I had been excited to play the hole for years prior playing it and somehow managed to stick it to two inches. My first one would have been really special there, but it will have to come another day.

17 is a straight downhill par four where you can drive it well over 350 yards. It originally played as the 18th hole back in the day. The current 18th plays uphill towards the massive mansion clubhouse. The green was definitely meant to mirror 18 at Winged Foot West, which Hanse was working on at the time, as it provides almost a staircase into the gorgeous clubhouse.

Walking with a caddie is mandatory at Sleepy Hollow Country Club. The course is only 6,902 yards long, but it is really hilly with some steep uphill and downhill walks. There is also a deep gorge where a series of wooden walkways are needed to traverse the gorge. In all, your conditioning will be tested during 18 holes at Sleepy Hollow.

Charles Blair Macdonald designed the course, which opened in 1914. Macdonald is considered the father of American golf course architecture. The project was for Cornelius Vanderbilt and the rumor is that these two strong personalities clashed, resulting in maybe Macdonald not giving his all to the assignment.

In the 1920s the land containing four holes overlooking the Hudson River were sold for real estate development. A.W. Tillinghast was hired to replace the four lost holes and also expand the course to 27- holes. As a result, Sleepy became a mixture of Macdonald and Tillinghast designs. Thirty years ago I did play Sleepy because the course was recommended as a “hidden gem.” After playing it, I was totally unimpressed by the ordinary look and was distracted by thousands of tall trees hugging almost every hole. Any view of the nearby Hudson River was totally hidden by these trees.

Gil Hanse has been involved at Sleepy with an extensive and years long renovation of the course. The first phase was 2005-2006. The second phase came in 2016-2017. It was Gil’s bunker rebuilds in the first phase that convinced the members that he was the guy to take on the massive transformation of the second phase. Wanting to use only one architectural style, Gil strongly recommended using Macdonald. In the second phase 4,000 trees were removed, bunkers (about 70) were reshaped, and all 18 greens were rebuilt (enlarged and squared). Now there is a bucketful of famous green designs to satisfy every lover of golf course architecture.

The massive tree removal has revealed spectacular vistas of the Hudson River. The course sits near a 300- foot-high bluff overlooking the mile-wide Hudson River with the cliffs of New Jersey in the distance. Between the course and the river is an invisible busy road and some houses. The first view of the river comes if you walk backward up the steep sloping second fairway. The real drama comes on the back nine.

In my opinion Sleepy Hollow ties with the Cal Club as the best restoration project in the USA since the turn of the century. Overseas, the best are Turnberry (Ailsa) and Yangtze Dunes.

The Odyssey

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.

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.

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!

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!

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.

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.

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.