#6, "Headless Horseman," Par 5, 475 Yards

If there's a hole at Sleepy Hollow that I wish I could play over again, it's the sixth.  It takes a big hitter to get to the top of the hill from the tee.  From the top of the hill, it's an easy shot to get to the green in two and have a chance at eagle.  However, if you don't reach the top, the next shot is blind with the Principal's Nose bunker waiting in the ideal landing area for a lay-up.  The Principal's Nose was added in the Hanse renovation, and definitely increases the strategy in the hole for those who aren't going for the green in two.  I didn't reach the top of the hill and was advised to just hit a 9-iron to make sure I stayed short of the Principal's Nose.  The strategy worked, but I think I could have hit more club and gotten closer to the green for a better chance to score.  If you're laying up, play your second shot well out to the left.

#13, "Andre's Lane," Par 4, 394 Yards

With the thirteenth, we're back to the original Macdonald/Raynor holes, and the rectangular coffin-style bunkers make it evident right away.  Aim down the left side of the fairway (at our caddy), as the slope will kick it back to toward the middle.

#17, "Hendrik Hudson," Par 4, 446 Yards

While the second hole played almost straight up a steep rise, the seventeenth takes the player back down.  In this case, the slope slants from left to right.  While it's a long par four on the scorecard, the contour of the hole will make for a longer drive with longer roll than usual, thus making the hole very playable.

#14, "Homeward Bound," Par 4, 380 Yards

The key to the fourteenth is to be as straight as possible to have the best angle into a narrow green.  Missing to the right brings trees and a ridge into play (see below--where I ended up!).

Looking backwards up to the hill to the top of the punch bowl.  The bunkers are at the top of the hill.

A view from the green, looking back at where the Principal's Nose lays in the middle of the fairway.

#3, "Haunted Bridge," Par 3, 167 Yards

The first one-shotter at Sleepy Hollow is the first time you get a feel for the mood that the Legend of Sleepy Hollow created, with a creepy-looking rickety wooden bridge taking you from the tee to the green.  It truly looks haunted!  When you muster up the courage to hit your shot, missing long and left is much better than short and right.

#1, "Sunnyside," Par 4, 417 Yards

The tee ball on the opening hole is to be launched from a tee box just below the clubhouse.  From there, the shot goes downhill to a fairway with a bunker on the right side.  If you bail out from that fairway bunker and miss the fairway on the left, a nearly hidden cross bunker will get in the way of running up an approach shot from the thick rough.  I felt good about myself when I this first green in regulation and thought I had a relatively short putt left for birdie.  However, I was fooled by the scale of this large green and still had a lengthy putt.  Greens at Sleepy Hollow are generally large, and generally very difficult.  Getting down in two putts is never simple, and it starts with this first green.

#5, "High Tor," Par 4, 403 Yards

The fifth is a dramatic point in the round, as it's the first hole that plays out to the Hudson River, providing a majestic view.  The drive is blind, but after reaching the crest of the hill, the hole, and the wonderful view reveals itself.  Favor the left side of the fairway from the tee to avoid a fairway bunker on the right, and also provide the best angle into the green.

#2, "Outlook," Par 4, 332 Yards

After the opening hole, the second hole turns away form the Hudson River, and goes steeply uphill.  Splitting the aiming bunkers on the hill is the proper line to land in this relatively wide fairway.  Those bunkers shouldn't ever come into play, but there are bunkers that will come into play for a poorly hit tee shot that goes short right or long left.  The green is also well defended by bunkers on either side, with the right-hand bunker bearing the shape of a check mark, hooking into the front of the green.  These bunkers are no joke...deep faces and flat bottoms.  Macdonald and Raynor would be proud.

#8, "Sleepy Hollow," Par 4, 462 Yards

The seventh hole is the last original Macdonald/Raynor hole for a little while, as this was formerly the edge of the property.  From the seventh, you would advance to what is now the thirteenth hole.  When Tillinghast came in to renovate the course, he built five holes onto a new section of the property, and created what is now #'s 8-12.  This stretch is what made the course a bit dis-jointed in the past as the style took a pretty drastic change.

The deep right-hand bunker at the 2nd, with the creepy wooden bridge and majestic 3rd in the blurry background.

My Quest to Check Off Golf's Best Experiences

#11, "Ichabod's Elbow," Par 4, 371 Yards

The eleventh hole bends to the right and finishes at a pushed up green with four deep bunkers guarding either side of it.  There are no fairway bunkers, but trees on the right and naturally rugged and rocky terrain on the left create enough trouble to make a straight drive necessary.

#10, "The Lake," Par 3, 172 Yards

The usual four template par threes on a Macdonald/Raynor course are the Eden, Redan, Short, and Biarritz.  In the case of Sleepy Hollow, the Biarritz has been relegated to the third nine holes.  The tenth hole is a Tillinghast hole, and is thus not a template, but still a good hole.  Playing over a lake, with another mysterious wooden bridge, it's a fun shot into the putting surface.  It was a dramatic moment for me on this one, as my shot hit the flagstick...we couldn't see the ball until we got closer to the green, so for a short time, we thought it might have gone in.  Even though it's a bit downhill, this shot tends to play the yardage.

#7, "Tarry Brae," Par 3, 217 Yards

Macdonald and Raynor were famous for building template holes on their courses from famous holes in the Europe.  There are a couple of good ones at Sleepy Hollow, beginning with the seventh (the third is the Eden hole; while it's a very good hole, it's an odd Eden in my opinion).  The Redan is one of the more well-known templates, with the green running away from the player to the left.  It favors a high right-to-left shot, which typically is shaped to avoid a bunker in the front left of the green.  In the case of the seventh, they build a reverse Redan, where a left-to-right shot is the ideal play.  In my opinion, reverse Redans don't work as well...at least for a right handed player due to the spin put on the ball of a faded shot, which will typically land softer and thus not advance along the ground as well.

Almost two hundred years ago, Washington Irving wrote his famous American classic, The Legend of Sleepy Hollow.  That legend still exists today, in the form of a world class golf course.  While clubs like Winged Foot and Quaker Ridge get most of the attention in New York's Westchester County, possibly the most beautiful and fun test of golf in the Upstate region might be the under-the-radar Sleepy Hollow.  It's so under the radar, that when researching the club, there's more information available about the clubhouse than there is the golf course.  While the clubhouse does have historical value, the golf is no slouch, and probably deserves just as much attention and acclaim.

Being a golf blog, I would usually start off by discussing a bit of the course's history, but in this case, the history of Sleepy Hollow begins with the aforementioned clubhouse.  Construction of the structure began in 1892, and finished in 1895, at a whopping cost of $2 million, which equates to over $50 million in today's dollars.  The 140-room mansion, known as Woodlea, was to be occupied by Cornelius Vanderbilt's granddaughter Margaret Louisa Vanderbilt Shepard, and her husband Colonel Elliott Fitch Shepard.  However, Colonel Shepard died before it was completed, leaving Margaret to live in the home by herself.  With nearly 70,000 square feet of living space and a commanding view of the Hudson River, this palace would seem to be good enough for anyone, but Margaret wasn't fond of it, and only spent the spring and autumn months there.  As years went by, she spent less and less time at the mansion, and began to shed portions of the property beginning in 1900, and ending with the final sale of the mansion in 1910 to Frank Vanderlip and William Rockefeller.  While the Shepards had put $2 million into the home, the 1910 sale occurred for only $165,000...quite a bargain for the new owners!  The new owners thought the home was too large to live in, but thought it perfect for other means, and by 1911 had convened a board of directors to begin a country club on the site.  Initial board members would include who's who names like John J. Astor IV, and Cornelius Vanderbilt III.  The club was incorporated on May 11, 1911.

Soon after organizing the board of directors, it was time to begin building a golf course on the sprawling grounds.  The club hired noted architect C.B. Macdonald to design the course, which was completed with the help of his engineering and construction partner Seth Raynor in 1911.  Where the Sleepy Hollow course starts to get a little funky, is in when the club brought in A.W. Tillinghast in 1935 to update the course.  Tillinghast was certainly no slouch of an architect, but the holes he built created a disjointed course, with several holes that had a Macdonald/Raynor feel to them, while others were distinctively more in Tillinghast's style.  To the club's credit, in 2008, the club hired Gil Hanse, who worked with Macdonald specialist George Bahto to renovate and restore the course to include more of a consistent flow of holes, while moving redesigning one hole completely.  What stands today is 27 holes of great golf on an absolutely gorgeous piece of land.  For Macdonald/Raynor buffs, some of their original holes are now on the club's third nine, but that doesn't take away from what stands on the main 18 holes.

My day at Sleepy Hollow was the first of two rounds that day.  After finishing up, we'd clean up and be off to the Hamptons to play Maidstone...quite the day indeed.  There was a bit of confusion when we arrived, as we were not being accompanied by members, and the starter/caddymaster wasn't ready for us.  However, he was quick on his feet, and immediately took care of the situation by pointing us to the first tee and tell us we could tee off right away if we were ready.  While it would have been nice to loosen up and hit a few balls, we didn't want to get in the way of the club's tee sheet, so he took a few practice swings on the first tee box and hit our white golf balls down the hill in the direction of the first green.  

When playing Top 100 golf courses, caddies are often part of the experience, and they run the gamut from young kids with little golf knowledge, to knowledgeable college kids, to career jocks.  At Sleepy Hollow, Patrick would carry doubles for our two-ball, and he was undoubtedly one of the more memorable caddies I've had.  He had it all; grizzle, experience, swagger, and a wit....my playing partner and I still laugh to this day about some of his one-liners and remarks, which ranged from obvious to ridiculous to hilarious!

While Patrick was getting our golf bags in order for the day's loop, we needed to determine an appropriate set of tees.  Sleepy Hollow has five sets of tees, with the Black Tees being the longest set and playing to a par 70 yardage of 6,880, while having a rating and slope of 74.0 and 137.  A course rating of four shots over par sounded a bit rough, so we agreed to play up one set of tees, and took on the Blue Tees, which still stretched to 6,618 yards with a rating of 72.5 and slope of 135.  I imagine most member play is from the White Tees, which are 6,343 yards.  I'll quote the Blue Tees below:

#12, "Double Plateau," Par 5, 541 Yards

While the twelve was part of the Tillinghast renovation, it's really more of a Hanse/Bahto hole, as it was substantially altered in the most recent renovation.  The hole used to be a straight par four with a green up on the hill that you'll see on the right side of today's hole.  Hanse and Bahto moved the green forward and to the left, and closer to the next tee, which created a par five, and also reduced the green-to-tee walk to the thirteenth hole.  Since they had a blank canvas to work with on the new green, they decided to go with a common Macdonald template green, the double plateau.

#16, "Panorama," The Par 3, 155 Yards

The most photographed hole is Sleepy Hollow is among the most beautiful vistas I've seen.  This is the Macdonald/Raynor "Short" template hole.  As usual for a "Short" hole, the shot isn't long, but the green is excessively large and undulating and placement on the surface is critical to avoid a three-putt.

#18, "Mansion Rise," Par 4, 426 Yards

The last hole at Sleepy Hollow returns you to the Vanderbilt mansion, or clubhouse if you prefer.  It's an uphill walk, and that, coupled with the yardage make it what some consider the hardest finishing hole in Westchester County...and they may be right.  The hole is a bear!

#4, "Brom Bones," Par 4, 422 Yards

The drive on the fourth hole is a bit on the blind side, with a bunker on the right side, which also happens to be the best angle into the green--no coincidence.

After finishing up, we changed shoes and cleaned up in the locker room, and it was off to Maidstone for our afternoon round.  We had a blast at Sleepy Hollow.  I guess in a perfect world, it would be nice if Macdonald/Raynor had completed their routing on the land that Tillinghast had used to make for a more consistent feel of the course, but the recent renovation have improved all of the holes enough that playing them is worth the slightly Jekyll & Hyde routing.  Kudos to the club for the commitment of bringing in Hanse & Bahto, because the makeover they completed on this masterpiece was tremendous.

#9, "Katrina's Glen," Par 4, 381 Yards

Hanse and Bahto cleared out a lot of trees in this section of the property to reveal natural land forms, and also to take away a bit of the long, narrow, gut-puncher feel, especially at the eighth hole.  The ninth has a really cool left to right flow to it as the hole bends along with slope of the land.  Bunkers flank either side of the green and need to be avoided.

Sleepy Hollow Country Club

Scarborough, New York


Checked off the Bucket List June 29, 2016

Golf Digest:

#15, Best in the State of New York (2015-2016)

#15, "Punch Bowl," Par 5, 457 Yards

The next two holes at Sleepy Hollow are one of the best one-two punches I've ever played.  The fifteenth is just a really fun golf hole.  The drive gets you into position, ideally on the right side to avoid being blocked by a large tree on the next shot.  The blind second shot is a blast and needs to come to rest in an awesome bowl of land.  The large flag behind the green is by the middle of the green.  Bunkers block the entry into the majority of the green, but a shot played out to the left will funnel its way down onto the putting surface.  After putting out, we spent a good amount of time just throwing balls around the sloping land to see where they would end up.  Oh yeah, did I mention the beautiful view of the Hudson too?  The photos don't do it justice.