I would compare yesterday’s activities to a round of golf where you make a couple of bogeys early, battle back to even par, then bogey the last two. Allow me to elaborate.
First off, this was our only 36-hole day on the leg of this trip, which concerned me. I am old enough for AARP, and this would be rounds 15 and 16 on the Where’s William Now adventure. I could feel my body starting to break down for a couple of reasons: (1) I’ve walked every round, and (2) I have been taking copious amounts of swings in each round. My game is not sharp and let’s just say I don’t wear a smart watch or Oura ring to track my fitness goals.
I’ve always had a weird body clock where I wake up at a certain time without an alarm if I am excited about something. In this case, my eyes opened at exactly 4am because that was when my found clubs were supposed to be delivered to the hotel lobby. As most of us do, I looked at my phone first and had an update–my clubs would now be delivered between 9am and 11am. So, me and the rental set would be having breakfast together after our terrible first date. In a bit of good news, I had traded out the kettle bell putter that destroyed my scorecard at Winged Foot the day before. Our host pro, Brett, who had witnessed the 43-putt carnage, brought me an array of options post-round. I’d selected an Odyssey Rossie half-mallet, which was slimmer and more visually attractive. Maybe this 2nd date had potential?
The plan was to have my found clubs transferred to Quaker Ridge via Uber, so I would be safely back into my long term relationship after the unsatisfying, regrettable two day affair. I was eager to see those babies because the grass isn’t always greener. As Trevino, Hogan, Nicklaus, Woods and many other all-time greats advise–if something works, don’t change it!
Quaker Ridge is right across the street from Winged Foot and was designed by A.W. Tillinghast. The course dates back to 1918 and has a very rich history. Byron Nelson won the 1936 Met Open here, and it hosted the Walker Cup in 1997 and the Curtis Cup in 2018. The GB & I Walker Cup team included a fresh-faced 17 year old named Justin Rose. The history of this place was palpable, with practice hours coordinated with tee times because the course fairways double as the driving range. Modern features like indoor full-swing simulators ensured members of Quaker Ridge had the proper mixture of past and present.
After a quick glance at the card, I made the questionable decision to join my 300 yard driving sons on the blue tees. This was my second soft bogey of the day. Upon further inspection, the yardage was not reflective of the actual length of the course because it only contained two par 5’s and four par 3’s. Each par 3 was between 150 and 180 yards. So, what that means is I was about to get put to sleep by a collection of demanding par 4’s between 400 and 460 yards. Not the ideal scenario when your driving distance is 248.7 yards per poke.
The first is a shortish par-5 getaway hole, which has a ghoulish green complex. Over the green is absolutely dead, and that is exactly where my ball was after hitting perhaps the longest pitching wedge of my life. My caddie, Ricky, said a million words with the look on his face. Anywhere on the green was going to be satisfactory. Flip it onto the surface, two putt, and limit the damage to a big fat 6. Then he saw me take a few practice swipes with my right handed, slot machine action, and his facial expression turned from concern to outright fear. I don’t know if I actually closed my eyes at impact, but the ball came out perfectly and landed in the rough like a hackysack about 2 inches from the green. It took a soft hop and then started rolling like a Ben Crenshaw putt towards the hole. Boom! Billy Buckets was back. Sadly, that would be the first and last birdie of my day.
The rental set driver and I were not vibing today, and if you’re not driving it at Quaker Ridge, you can forget it. The collection of par 4’s are longish and force you to work the ball left and right off the tee with out of bounds to the right on the first 8 holes The course continually challenges you to put the ball in the right position off the tee and then into the greens. If you fail either of these examinations, you are likely making bogey or worse. The green complexes are raised and surrounds are tightly mown. The bunkers are perfectly placed. And it is visually stunning after a recent redesign by Gil Hanse that opened up the views around the property.
We have had excellent caddies on this trip, but we really hit the jackpot with Ricky and Yelly. Sometimes 1 plus 1 equals 3, and these two dudes really enhanced our experience. Ricky was at least 10 years younger than me and had been at QR for 31 years. Yelly started caddying at QR when he was 13. He is from Senegal and is finishing his degree up at Penn State with a science/technology degree. They kept us positive and in stitches the entire day.
In the end, Tillinghast gave me the business. I finished with a 78, otherwise known as Old Man Club Pro par. The Rossie did its job, and I think I improved by 10 putts versus the day previous. The miracle chip in at the first didn’t hurt the putting stats either.
After unpacking my real sticks and grabbing a quick lunch to go, we arrived at Sleepy Hollow about 8 minutes before tee off. My sons had been geeking out on the SH logo for the entire drive, which is the famous Headless Horseman and routinely ranked as the best club logo in America. Our host, Charlie, had called my cell to confirm we were still coming. Hell yeah, we’re coming!
Dad isn’t as quick as he used to be, so by the time I got myself organized, we were on the first tee. We got dealt a couple of pocket aces again with our caddies, Matt and Connor. Charlie, the Merchandise Manager and my sons’ new best friend, is a lefty and can really play. Once again, I was guilted into the blue tees and another round as the D player.
The first hole is a flattish par 4 that doesn’t give you any indication of what is to come. By the time we reached the 2nd tee, it became obvious that the property had some topography we’d yet to encounter on this trip. My goal immediately changed from finishing the round to finishing the 2nd hole because it is STRAIGHT uphill. Gasping for oxygen, I made a slippery three footer for bogey and, if we didn’t have a short recovery wait for the group in front on #3, an airlift would have been a possibility.
Every hole at Sleepy Hollow is visually stunning. There are a few blind shots and approaches, but that just adds to the mystery of the course–which I think is perfectly on brand with the name, logo, and history of the club. And each hole challenges you in terms of slope, elevation change, and infinity green complexes. The fairways are fairly wide for the most part, but bunkers pinch in key areas and there are several tee shots that demand a certain shape. The front nine was a 9.7 out of 10, and then we stood on the 10th tee in the back corner of the property and my evaluation escalated quickly.
The 10th is a downhill par 3 over water with the coolest bridge I have ever crossed in golf. The 11th is a dogleg right par 4 to a raised green with native grasses, trees, and rock outcroppings up the right side. And the 12th is a dogleg left par 5 to a raised green with a meandering stream up the left side. When we finished the 12th, I had made my final decision. These were the best three inland holes I have ever played in succession, which is quite a statement because I have played 70 of the top 100 courses in America.
So, I don’t know if I had reached the pinnacle of my golfing life after the 12th hole or someone hit me with a tranquilizer dart from the trees to the right of 13, but Gramps hit the WALL. My legs were GONE and I deteriorated from my usual slow trudge to a wobbly limp. I’m sure I looked like I’d stumbled out of an Irish Pub after too many Guinness, but of course that never happened on Leg 1 of the Where’s William Adventure. But if there is one compliment I will graciously give myself–I am no quitter.
The 14th hole had one of the best green complexes I’ve ever seen, with the surface featuring ridges like a potato chip. The unique 15th I didn’t play as it was intended, but my youngest son hit one to 5 feet on the Punchbowl green for a birdie. The 16th is one of the most talked about holes in golf, with its famous thumb print green and views across the Hudson River. After standing there, I now see what all the fuss is about. The 17th is a sharp downhill par 4 with expansive views and the 18th reminded me a bit of the 18th at Riviera. Except the 18th at Riviera doesn’t have a greenside bunker 20 feet below the green surface–which of course I found for one final uppercut. In the end, I bogeyed 4 of the last 6 for a 78 and almost tripped walking up the stairs to the car–TWICE. Despite my punchiness, I knew I had just played one of my Top 5 courses of all time.
Winged Foot East today! I have my faithful Jailbird putter with extracted me out of a few jams at Sleepy Hollow yesterday. I predict a much better performance if I can get some blood into my legs for another 10 mile walk. Please pray for me.




