Westchester's 18 Hardest Holes (and How to Beat Them)

Golf courses are designed with trouble in mind.

Golf, it is often said, is a game of misses. And when we miss in golf, we get in trouble. Our ball ends up in the tall weeds, or a bunker, or behind a tree, or — this actually happened to me — under a table in a halfway house. Trouble can also come in the middle of the fairway if your ball is on a severe upslope, or there’s an overhanging tree limb between you and the green. Golf courses are designed with trouble in mind, so we have to know how to recover from errant shots with the least amount of damage to our score. (In case you’re wondering, I took a free drop for my ball under the table, since it was an immovable obstruction.)

Our composite course this year is made up from some of the most troublesome holes in Westchester. It measures 7,080 yards from the member tees and plays to a par of 72. To help alleviate some of the pain you might endure while playing it, we asked our local pros how to play the many kinds of trouble shots you might need. Short-sided in a bunker? Chipping off a super-tight lie? Tangled in the fescue? Save your score with the help of our pros.


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– 1-

Angelbrook Golf Club


No. 7 395 yards par 4

Most of us consider fairway bunkers trouble enough, but when they sprawl into the fairway landing area like the monster on Anglebrook’s 7th hole, it’s enough to make a grown golfer cry. The hole should actually be a pretty straightforward par, although the shot from the fairway into the shallow, well-bunkered green can be bothersome. Landing your drive in that bunker, though, changes the complexion completely.

Head pro Rob Davis has three pieces of advice for dealing with a fairway bunker like this one. “First, don’t panic. Realize the only difference between a sand shot and a play from the rough is that the sand can give way in your stance if you try to swing too hard. So rely on your basics.”  Secondly, he says, “Decide what the most challenging variable is. Soft fluffy sand? There’s more room for error and slippage so you should probably opt for a safe play back into the fairway for your next best shot. Firmer sand? Have at it! The shot is more like a nice solid fairway strike.”  Finally, he has one last piece of advice: “If you’re going for the green, err on the side of more distance. Take more club and settle into your back leg for a good solid base.”


– 2 –

Saint Andrew’s Golf Club


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No. 15 368 yards par 4

You don’t need a long hole to find plenty of trouble on a golf course, as the 15th hole at Saint Andrew’s demonstrates. The short dogleg takes the driver out of most player’s hands in an absolutely essential effort to avoid the water that begins about 130 yards off the tee to the left and the trees that wait in the crook of the dogleg on the right. Hitting to the center of the fairway still leaves plenty of trouble on the hole, with a pond lapping the green across the front and a putting surface that’s only 14 yards deep, waiting for your second shot.


– 3 –

Metropolis Country Club

White Plains

No. 11 573 yards par 5

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Sometimes trouble comes when you feel you least deserve it, something that happens all too often on the long up-and-over the hill 11th hole at Metropolis. You may have striped a fine second shot over the crest of the hill and down the middle of the fairway only to discover when you reach it that your ball is perched precariously on a downhill slope. The green is easily reachable, but how do you control your shot?

“Manage your expectations,” recommends assistant pro Lynn Bernstein. “You may have some balance issues, so you won’t want to swing quite as hard as usual. Take a wider stance than normal with the ball back about an inch and your shoulders parallel to the slope. When you swing, keep your lower body a little quieter and swing ‘down the slope,’ as if your club were chasing the ball. The whole idea is to make solid contact despite the slope.”


– 4 –

Winged Foot Golf Club


East Course, No. 6 196 yards par 3

The 6th hole on Winged Foot’s East Course inspired this year’s theme. Its name? “Trouble,” of course. For a par three, it’s remarkable how much trouble A.W. Tillinghast built into this one golf hole. From the tee, you see three greenside bunkers, as well as a fairway bunker that serves no purpose other than to plant some fear among your swing thoughts. At 196 yards, it’s a long hole already, but it plays uphill, so you’ll need an extra club. And there’s a false front on the green, too, so you might want an extra club and a half. About the only break you get is the backstop on the green, which slopes back to front — although that also means you need to stop the ball quickly, or you’ll be putting from above the hole.


– 5 –

Westchester Country Club


West Course, No. 6 435 yards par 4

You can eliminate the first spot of trouble on the number-one-rated hole on Westchester’s West Course by hitting a dead straight 250-yard drive. Even better, hit one 280 yards with a slight fade to get around the huge trees lining the dogleg. Either way, you’re still left with a daunting shot downhill to an elevated green whose front alley is flanked by bunkers. Your trouble isn’t over once you have the flat stick in your hands, though, since the 6th green has multiple tiers, and there’s not a straight putt anywhere on it.


– 6 –

Leewood Country Club


No. 9 184 yards par 3

“Beauty and the Beast” should perhaps be the nickname of the picturesque but deadly 9th hole at Leewood. The hole is framed by stately trees, fronted by a lovely pond, and guarded by pristine bunkers that sharpen your focus on the green. Unfortunately, that’s where “the Beast” lives. The 9th green is both sloped and slick, meaning that if you are above the hole when you putt, you’re in serious trouble.

Head pro Dean Johnson says that even though you may have to aim your putt away from the hole in severe situations, it’s still possible to stop your ball near, if not at the bottom of, the cup. “Control distance with how far you bring the putter head back,” Johnson advises. “You can hit off the toe to deaden the stroke, but that brings a lot of uncertainty into the stroke. You still want to hit the ball solidly to get it rolling well.”


– 7 –

Quaker Ridge Golf Club


No. 16 414 yards par 4

The 16th hole at Quaker looks peaceful and benign, but beware the bunkers. There’s one just off the fairway on the right, about 240 yards from the tee box expressly designed to punish moderate faders of the ball who can’t hit and hold a 25-yard-wide landing area. The elevated green has two deep bunkers guarding either side and a backstop bunker that
will put a quiver in your knees as you realize anything but a perfect sand escape from there will probably run through both tiers and the false front back to the fairway — or into one of the other greenside bunkers.


– 8 –

Knollwood Country Club


No. 5 535 yards par 5

One feature added to Knollwood during the club’s recent restoration is deep fescue rough in several places on the course, which both adds wonderful texture and color to the landscape and inspires nightmares for errant golfers unlucky enough to land in it. One of the most punitive spots on the course for the knee-high cabbage is on the 5th hole, an uphill par 5 that has a demanding two-tiered green with deep bunkering.

If your tee shot finds the fescue, according to head pro Bob Miller, “The first thing to do is see what kind of lie you have. If the grass is wispy and the ball is sitting up, you may be able to advance toward the green. Otherwise, you should just take your most lofted club and try to get back into the fairway. Put the ball back some in your stance, put your weight on your front foot, and take a firm grip with both hands, to keep the club from twisting when it hits the grass. Hit down on the ball — don’t try to lift it out — and swing hard!”


– 9 –

Apawamis Club


No. 7 416 yards par 4

The recent renovation at Apawamis marked a quantum improvement for the venerable club in Rye. Most notable were new bunkers on many holes, extensive tree removal, and some exciting new tee boxes. Easily overlooked, though, is the removal of rough on the hardest hole on the course, the 7th. While you might think it makes the tee shot less risky, the lack of rough actually makes an accurate drive — preferably a long draw — even more important, since a fade that’s slightly overdone will now run and run in the wrong direction on the close-cropped fairway, rather than stop in what used to be moderate rough. You will be left with a great lie, but a very long approach shot to a green that runs away from the fairway.


– 10 –

Willow Ridge Country Club


No. 18 485 yards par 5

The finishing hole at Willow Ridge tests not only your golf game but your cardio fitness, as well. It plays steeply uphill, and, regardless of how long you are off the tee, you will have at least one swing where gravity is not your friend. Teaching pro Kyle Baehler says a few simple adjustments can help you get the ball to the green.

“It’s mostly about the setup,” he says. “Depending on how severe the hill is, take a wider stance because you’re going to be thrown off balance a bit. Play the ball a little forward in your stance and aim a bit to the right. I’ve found that the ball tends to go slightly left from that setup. Finally, align your shoulders with the slope, so they’re parallel — that will help you make better contact.”  Baehler adds, “Take one more club than you normally would from that distance. You’re going to be adding loft because you’re swinging uphill. Hopefully, too, you won’t swing quite so hard, so you may need a little extra club to get there. Be sure to take a smooth, short swing.”


– 11 –

Wykagyl Country Club

New Rochelle

No. 8 446 yards par 4

The trouble hits you right in the face on the tee on the 8th hole at Wykagyl. It’s a classic risk-and-reward shot, but the penalties for failure can be pretty severe. The hole is a sharp dogleg left, and long hitters will be tempted to fly the corner to set up a short-iron approach. An overaggressive draw, though, will put you at best in some thick trees and at worst in a maintenance garage. The conservative player can still conquer the dogleg with a 235-yard carry, but a slight miscalculation will leave you with a long blind shot to a narrow green guarded on both sides by bunkers.


– 12 –

GlenArbor Golf Club


No. 17 189 yards par 3

A perfect tee shot on the penultimate hole at GlenArbor will find the capacious green, but how many of us hit perfect tee shots? A good miss on the long par 3 will stay out of the bunkers (and the greenside lake) but still leave you with a tricky chip off a tight lie that you have to get close to put a par on your scorecard. Director of Golf Rob Labritz says you have two options: Either fly the ball to the hole with a wedge, or hit a low-running chip with something like an 8 iron, choosing whichever shot gives you the most confidence.

“The key to any shot off a tight lie is to use the bounce of the club to avoid chunks and skulls,” he says. “To play either shot, take a narrow stance with the ball in the middle, so the club will strike it at the bottom of your swing. Keep your feet, hips, and shoulder square to the line with about 60 percent of your weight on your front foot. Then take an “armsy” swing, keeping your lower body still.”


– 13 –

Bedford Golf & Tennis Club


No. 7 392 yards par 4

Every shot you hit on the number-one handicap hole at Bedford Golf & Tennis Club is tinged with danger. Your tee shot needs to fly 235 yards to reach the dogleg and give you a shot at the green, but 250 and straight will put you through the fairway into the rough, leaving a next-to-impossible second shot.

Even from the fairway, you’ll need at least one more club and probably two to carry your approach to the tiny green atop the steep hill in front of you. Come up short, and you’ll be lucky if your ball rolls back and stops in the fairway instead of the thick rough on either side of the narrow-approach alley.


– 14 –

Ardsley Country Club


No. 3 419 yards par 4

You encounter all too many ways to get in trouble on the 3rd hole at Ardsley. There’s a creek cutting across the fairway that bedevils the short hitter off the tee, out of bounds straight ahead that catches the long hitter and a green that’s protected by both water and several deep bunkers. Despair can easily set in if you navigate all the trouble only to find yourself short-sided in one of those sandy graveyards.

“Your only thought should be to get the ball out in one stroke,” advises teaching pro Christi Dorece. “Use your most lofted club and open the club face slightly. Get the club up in your back swing, so you can generate plenty of swing speed. You need to accelerate through the shot, and keep the club moving through the sand at all costs. And follow through!” She adds that if you need one swing thought, it’s to “splash the sand onto the green.”



– 15 – 

Hudson National Golf Club


No. 16 224 yards par 3

Length off the tee is only one kind of distance control you’ll need to overcome the trouble on the Hudson River vista-endowed 16th hole at Hudson National. The green is so large, it’s actually fairly easy to hit as long as you take enough club and aim for the center. Even a miss into the gnarly rough or one of the two massive bunkers doesn’t necessarily spell doom, since there’s plenty of green to work with if you need it. That also means, though, that you may have a long, long putt for par. The green is a full 100 feet deep and 90 feet wide, so hone your lag putting technique before you play!


– 16 –

Trump National Golf Club

Briarcliff Manor

No. 12 530 yards par 5

Three kinds of trouble await you at the first par 5 on the back nine at Trump National Westchester. First, you need to drive your tee shot in bounds and into the narrow fairway, then you have to overcome your natural urge to hit a hero second shot 270 yards over the barranca in front of the green, and finally, you have to really take dead aim with a wedge to save par, since you incurred a penalty stroke by NOT resisting your urges on your second shot.


– 17 –

Fenway Golf Club


No. 14 421 yards par 4

Trouble on the longest par 4 on the back nine at Fenway begins on the tee, when your drive has to avoid OB on the left and a thick stand of trees on the right. The greatest danger, though, lies in the five bunkers that begin 80 yards in front of the green and spell doom for many players.  “The long bunker shot is the one shot you want to avoid at almost any cost,” according to Fenway’s head professional, Heath Wassem. You can’t use your usual greenside bunker technique, nor do you have the full-swing leeway that typically comes from a fairway bunker.

To save par, Wassem says, “Shorten up on the grip about an inch, to be sure to catch the ball before you catch the sand. The ball goes back in your stance for the same reason — so you connect with the ball on the downswing. Be sure to allow for a low, line-drive trajectory that will roll a little bit more than usual, but take enough club to make sure you don’t leave the shot short of the green. When you swing, your weight should be somewhat on the front foot, but there’s no weight shift at all.”


– 18 –

White Plains

Hole No. 2 438 yards par 4

Long, straight drivers of the golf ball won’t have any trouble parring the second hole at Westchester Hills. The other 98 percent of us, though, may have to deal with a low-hanging tree branch or two or three if our tee shot strays from the fairway, where it so seldom lands. Trees line both sides of the short grass and really pinch it where it turns toward the green in a slight dogleg right, so it’s entirely possible you’ll need to play under or around an arboreal obstacle for your third shot, too. Golfers who have only a high-flying trajectory with their irons may struggle on this hole if their tee shot doesn’t find the fairway.

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