Daredevil’s Delight

Eighteen holes with high risks and high rewards

Daredevil’s Delight 18

Holes Ruled by Risk and Reward


By Dave Donelson


Baseball has the suicide squeeze, football the two-point conversion—dangerous plays that offer a big payoff when they work but brutal punishment when they don’t. In golf, it’s the risk-and-reward hole that adds an extra dose of excitement to the game. Not every course in Westchester has one, but some have several. They’re usually not the hardest hole on the course, but they’re often the most debatable and always the most dramatic.


The classic risk-and-reward hole is usually (although not always) a fairly easy par that offers the average golfer an opportunity to go low by taking a chance on hitting a great shot and scoring a birdie. Risk-and-reward holes encourage the eternal hope that springs in the heart of every golfer. Hope that you’ll drive the ball 280 yards instead of your usual 230. Hope that you’ll somehow hit a high soft fade to the green instead of a screaming slice into never-never land. Hope that just this once you’ll make the shot you’ve always dreamed of.


This year, we designed an entire imaginary course made up of our favorite, very real, risk-and-reward holes in Westchester. Our criterion for considering a hole was simple: If you take the risk offered, you can make a birdie. If you blow it—even by a little—you’re almost certain to make a bogey or worse. No easy scrambles allowed. It’s a shot maker’s course and a gambler’s delight. Our track is short, only 6,261 yards, but that’s in keeping with the nature of the holes—driveable par 4s, par 5s you can reach in two if you have the guts, even par 3s that call for more strategy than strength. Par is 72, but the course record (if one existed) would be 54—a birdie on every hole scored by a golfer who takes all the risks and reaps all the rewards.



1. Fenway Golf Club  


Hole No. 1      285 Yards       Par 4



The first hole at Fenway is soooo tempting. The front of  the green is only 270 yards from the tee—the center just 285! Head Pro Heath Wassem says that for an easy start you should just take a hybrid off the tee to comfortable wedge distance, pitch on for a two-putt par on the large, rolling green, then go on to the next tee. But why begin your round with a par when you can get a jump on the game with a birdie—or even an eagle? Besides, layups are for basketball, aren’t they? All you have to do is hit your drive a few extra yards to that huge, inviting green. Pay no attention to the acres of sand surrounding every approach angle, or to the trees on the right waiting to turn a slice into a pitch-out bogey. Just bomb it!



2. Pelham Country Club

Pelham Manor

Hole No. 4       330 Yards      Par 4



What a choice you get on the tee at Pelham’s fourth hole—
a nice, safe long iron or hybrid to the landing area at the bottom of the valley, or an aggressive, accurate driver to the other target half way up the hill to the green. The problem with the safer option, according to head pro Mike Diffley, is that it leaves you a long blind second shot to the green, which is guarded by bunkers right, front, and behind. Of course, the other option off the tee has more than just a hint of danger to it. The second landing area itself is only about a third the size of the safe one—and you need to hit a strip the width of a shoelace on the left side to keep from spinning your ball off into oblivion on the right. If you’re short, you’ll be hitting your second shot—or trying to hit it—out of ankle-deep rough from a side-hill, up-hill lie. The reward for a well played shot is a great one, though, since you’ll have a short pitch to a radically canted green that’s tough to par from the lower area.


3. Knollwood Country Club


Hole No. 13       379 Yards       Par 4



There are two successive risk-and-reward holes at Knollwood, and we had a tough time choosing between them. The 13th won, mainly because the risk is one a sane person might actually take and have a chance to pull off. All it takes is a high drive over the trees that form the 90-degree right dogleg. As head pro Bob Miller advises, “It plays shorter than the measured distance because it’s downhill. Aim it just left of the tenth green. If you carry it far enough, you can hit the thirteenth green.” Miss in any one of several directions, though, and you’ll need at best a delicate sand wedge or at worst a chainsaw to get to the green for something north of par. After the 13th hole, you get to play another risk-and-reward hole, a short par 4 that’s perfectly drivable if you carry a howitzer in your bag that can blast the ball 287 yards horizontally and 50 yards vertically over the pines to drop straight down onto a green the size of a bottle cap.


4. Trump National Golf Club

Briarcliff Manor

Hole No. 5      490 Yards      Par 5



You may have to be insane to take the risk 
presented by your second shot at this wind-whipped,
water-bedeviled par 5. But why not? This is America, where anybody can become a billionaire or even hit a perfect, high 230-yard fade from a draw lie—one that not only carries the water, but goes over or around that really inconveniently placed tree in the fairway and lands like a butterfly on the elevated tabletop green. Of course, you can always play it safe, hit to the nice, tame lay-up area left of the green, chip on, putt twice, and write a five on your card. You could also put your savings in municipal bonds, but nobody gets to be a billionaire that way.


5. Winged Foot West


Hole No. 3      216 Yards      Par 3



You don’t win U.S. Opens at Winged foot (or anyplace else) by taking chances. Just ask Phil Mickelson. Still, the temptation is there. Like on the long par-3 third hole on the West Course. If  you hit the green from the tee, you’ve got a legitimate birdie chance, because the green isn’t too rolling or too steep to sink your first and only putt. That’s a big “if” though, since the green is small and a long way from the tee. If you miss right or left, you’re in deep sand or in the thick, twisted rough (and maybe under or behind a tree as well). Try to get up and down from that for a par. Or you can play it safe, as Billy Casper did in 1959, when he laid up to the front of the green every day off the tee, chipped on, putted once for a par, and won the U.S. Open.


6. Century Country Club


Hole No. 12      357 Yards Par 4



In some ways, the safest way to play this little dogleg is to take the risk and drive over the fairway bunkers on the left. As head pro Nelson Long explains, “That leaves you with a thirty- to fifty-yard pitch to a narrow, well-bunkered elevated green.” The risk is if your long drive is pushed even slightly right, it will find the pond at the end of the fairway. The so-called “safe” play is a 200-yard tee shot, short and right of the bunkers, but that forces you to make an exacting short-iron shot from a difficult angle. The longer your drive in the fairway (assuming you don’t hit through into the water), the more delicate your approach shot has to be.


7. Ardsley Country Club


Hole No. 3      419 Yards      Par 4



Early in your round at Ardsley, you’re faced with a  man-sized par 4 that you can trim down to a makeable birdie opportunity with a long, high draw over the trees on the left. Miss that long drive, though, and you’re in trouble—those maples are there for a reason. You’ll either be blocked from reaching the green at all with your second shot or have at best a long, long recovery shot. The safe route is the wide fairway to the right, where you’ll then face a second shot with a long iron or hybrid. Even that’s no guarantee of a par, though, since it’s tough to land your approach in just the right position on a green that is the size of Rhode Island and has more curves than a kettle-fried potato chip.


8. Quaker Ridge Golf Club


Hole No. 9      143 Yards       Par 3



An accurate aim counts on par 3s, but distance control  is paramount on the really good ones, like this short one-shotter that Jack Nicklaus reportedly said is harder than Winged Foot West’s famed 10th hole. The triangular green is about the size of your dining room and has a back right shelf not much larger than a table for four, which makes for one very devilish pin position. As head pro Rick Vershure explains, “Plenty of top players in the Hochster Memorial shoot for that pin and regret it. If they go long, it’s almost impossible to chip back without running all the way down the steep green—and sometimes off the front into a bunker.” The safe play is short, so you’re well below the hole with a chance at making your long uphill putt.


9. Wykagyl Country Club

New Rochelle

Hole No. 9      500 Yards      Par 5



Wykagyl Country Club opened an almost new golf course in 2007, the result of a massive overhaul that altered the character of nearly every hole. One of the biggest changes was on the ninth, a formerly tight, almost restrictive, par 5. When the architects removed dozens of trees on the hole, they might as well have put up a billboard above the clubhouse with “GO FOR IT” in giant letters. It’s now a true risk-and-reward hole because, according to Head Pro Ben Hoffhine, “you now have the option of going for the green in two. You just have to steer clear of the deep bunkers guarding the green.” Those bunkers aren’t just next to the green, either. They stretch back about a hundred yards along the left side of the fairway, just waiting to swallow up a risk-taker’s misguided ball.


10. Westchester Country Club West


Hole No. 1     314 Yards Par 4



A good risk-and-reward hole can break your heart or reward you with a trophy. The first hole at Westchester Country Club has done both many times. At 314 yards, it’s drivable if you dare. It’s also eminently missable, as Seve Ballesteros found when he tried to reach it during a playoff with J.C. Snead for the Westchester Classic Championship in 1987. The gallant Spaniard went for broke, but something—a little too much right hand, a slight restriction in his turn, maybe a flighty right elbow—sent his drive sailing down the hill left of the green, the last place you want to be on this hole. Snead watched Ballesteros take the risk and miss, then put his own driver back in the bag, laid up, pitched on, and won the tournament.


11. Willow Ridge Country Club


Hole No. 12    537 Yards       Par 5



The elevated tee box at this straightaway par 5 is like hitting from the observation deck at the Empire State Building. You just know your drive is going to go a long, long way, leaving you a solid chance at reaching the green in two. You also get a great look at the major risk on the hole, the ball-snatching little creek that runs across the fairway right in front of the green. Remember that view, because you probably won’t see the creek when you’re lining up your go-for-broke second shot from down on the fairway. Of course, you can always lay up to the water and pitch on for a par, but where’s the fun in that?


12. Sleepy Hollow Country Club


Hole No. 3     160 Yards       Par 3



“Don’t slice, don’t slice, don’t slice” is the mantra chanted by players facing the third hole at Sleepy Hollow. Less famous than its photogenic brother, the 16th hole, the third presents its own challenge to those willing to risk firing at a pin anywhere on the right side of the green. Send your tee shot just a little bit more than you should in that direction and you’ll land in the greenside bunker—if you’re fortunate. Miss that particular trap, and your ball is headed for the bunker below it, where you’ll be lucky to see the flag, much less the hole. If you get a bad bounce, you’ll be trying to get up and down from the valley of doom.


13. Bedford Golf & Tennis Club


Hole No. 6      358 Yards      Par 4



How can you resist going for the gusto on this short, downhill, dogleg
left par 4? All you have to do is drive your ball 250 yards or so over the innocuous looking bunkers in the crook of the dogleg, where it will catch the slope and roll another hundred yards, almost to the green. The risk, of course, is in those bunkers—six of them—which aren’t quite as harmless as they look from the tee. As Head Pro Tony Chateauvert points out, “If you twitch a little bit and pull it, you’re in one of those traps.” And if that happens, you’ll have the toughest shot in golf—the long bunker shot—downhill to a green that has no intention of letting your ball stop anywhere near the hole if it comes in without any backspin, which is what happens when you hit the ball a long way out of the kitty litter.


14. GlenArbor Golf Club

Bedford Hills

Hole No. 16      337 Yards        Par 4



The 16th at GlenArbor is a real shot-maker’s hole, according to Director of Golf Rob Labritz. You see all the options from the tee. Play it safe and short to the middle of the widest part of the fairway, avoiding the water left and long and the trees to the right, and you’re left with an easy short iron over the water to the big, multi-level green for a straightforward par. Or, take a risk and go long. If you have pinpoint precision, you can thread your drive up the right side of the ever-narrowing fairway between the water encroaching from the left and the trees squeezing in from the right. The farther you hit it, the narrower the landing area—but the better your chance of landing your approach shot close to the hole.


15. The Apawamis Club


Hole No. 16     180 Yards      Par 3



The only golf shot I know of that’s named after a real person is the Patroni, which is the tee shot preferred by smart players of the par 3 16th hole at Apawamis. The members swear that Jack Patroni, club pro in the 1960s, never went for the dangerous green from the tee, preferring to lay up with a six iron, chip close, and make a one-putt par. It’s a wise choice, too, because the risk-taker who goes for the sternly-protected green brings into play three traps on the right side, a pot bunker on the front left, and the tangled rough down the bank behind the green. Even a tee shot that hits the target can be a disaster if it’s above the hole on the precipitously inclined green. 


16. Leewood Golf Club


Hole No. 14      307 Yards Par 4



Leewood’s most famous member is undoubtedly Babe Ruth, whose memory is celebrated there in a lounge off the men’s locker room full of his pictures and memorabilia. The Babe was so proud of playing at Leewood, he placed the trophy he won there in 1938 in his space at the Baseball Hall of Fame. It’s a sure bet the Sultan of Swat never, ever laid up to the lake on the 14th hole, a short downhill par 4 where the water stretches across the entire fairway, ready to swallow anything less than a home run. Word has it that the Babe not only carried the lake (a drive of about 270 yards), but actually drove the green a few times, no mean feat in the days of persimmon drivers and pneumatic-core balls. Bunters are advised to lay up off the tee and take their chances with a wedge over the water to the two-tiered green.


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