The 18 Hardest Holes In Westchester Golf

The county holes most likely to jump off the scorecard with a bogey, a double—or worse.

When was the last time you shot even par? Okay, that was an unfair question. Unless you are in the tiny group (less than two percent) of golfers who have a handicap under one, the answer is almost certainly “never.” Let’s face it: Most of us are bogey golfers, shooting an average round of 18 over par most of the time. In fact, I would wager the majority of casual golfers would be quite pleased to break 90 with any regularity.

Quite frankly, that’s probably not going to happen on our “Bogey Nightmare” course. According to the pros we surveyed (and our personal research), these 18 holes are the ones most likely to jump off the scorecard and smack a bogey golfer in the face with a double—or worse. In fact, quite a few of these holes could give a scratch golfer some agita as well. But don’t despair! We asked the pros how the bogey golfer can protect his score through good course management and intelligent play. As you consider their answers, keep in mind what Bobby Jones famously observed: “Competitive golf is played mainly on a five-and-a-half-inch course…the space between your ears.”

Brynwood Golf & Country Club

Hole 8 216 yards par 3

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“For a bogey golfer, the most important thing stepping onto our eighth hole is to be on the right tee box,” advises head pro Michael Mercadante. “A lot of golfers try to play from the back tee, and so they have to hit driver—and hit it perfectly—just to get it there.” On the scorecard, the hole doesn’t look like it requires a driver. When you see the water and bunker in front of the steeply elevated green, though, you realize it takes a mighty blow to reach the putting surface. “Your best miss is to come up short,” Mercadante says. “You don’t want to miss left or right because you have a daunting chip to the undulating green. From the front, you can use a little backstop on the green. Short and right of the bunkers works for a lot of players. They then get on and have a putt for par or hopefully at worst a two-putt bogey.”

Ardsley Country Club

Hole 9 456 yards par 4

“This has always been recognized as one of the best ninth holes in Westchester,” says head pro Jim Bender. “It’s very picturesque with the lake behind it. The hole is a slight dogleg left, but the best place to hit off the tee is to the right center of the fairway.” That’s because some of the trouble is out of bounds left the entire length of the hole. There’s also a creek and out of bounds to the right, though, so keeping your ball in play off the tee is job No 1. Because the hole plays uphill off the tee, the second shot is usually a long one, and most bogey golfers need to hit another 220 to 250 yards to reach the green. “Even a good player doesn’t hit the green a lot in regulation,” Bender says. “It’s tough, too, because you can be playing a good nine and just come off a nice par three, and suddenly you’re faced with this long uphill tee shot on the ninth hole.” Just to make it interesting, Bender explains, “There’s a maple tree protecting the right front of the green, so you have to aim your shot left-center.”

More: 27 Westchester Golf Courses You Need To Play 

The Golf Club of Purchase

Hole 7 508 yards par 5

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Carl Alexander, head pro at The Golf Club of Purchase, advises players to maintain their focus and not get distracted by the beautiful surroundings of the seventh hole, a three-shot par five. He also says, “This is no time to have negative thoughts. You must hit the shot you know you can. It doesn’t have to be pretty, just in play.” Avoiding penalty strokes may be the most important strategy for the bogey golfer on this hole. Alexander points out that hazards are a threat from the tee, so he suggests throttling back and swinging at about 95 percent. “Focus on solid contact, and maintain your balance,” he advises. A solid drive favoring the right side can carry the hazard and set up the next shot.  

Your second shot is to a narrow landing area surrounded by wild environmental areas on both sides. Going for the green isn’t really an option for the bogey golfer, so Alexander suggests choosing a hybrid to midiron in order to leave a comfortable distance into the green for the third shot. “You’ll be playing into a green measuring just 14 paces wide at its narrowest point and 18 paces at the widest,” he says. “And this shot must carry a rock wall that faces you in front of the green.” There is a bank behind the green that can kick some balls back on the putting surface, but any ball that stays up there is facing a tough chip back toward the hazard. 

Alexander offers a final encouraging word: “With a relatively flat green, once players find the putting surface, they are rewarded with a good chance to make a putt.” 

Westchester Country Club West

Hole 6 430 yards par 4

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Westchester Country Club Director of Golf John Kennedy points out that the sixth hole on the West course tests every golfer with two long shots to one of the most difficult greens of the 18. The hole is a long dogleg right, which means choosing the right set of tees is crucial for the bogey golfer so he or she can reach the crook in the dogleg. “Even if you get it past the trees on the right,” Kennedy says, “you’ll have a long, long, second shot up and over a hill. It’s not a bad idea to play to the landing area in front of the green rather than try to reach it in regulation since the throat between the bunkers guarding the left and right side of the green is only 11 yards wide and misses are expensive.” He says it’s not a bad idea to play short of the throat so you can have a solid pitch or chip up the false front and onto the two-tiered green.

Quaker Ridge Golf Club 

Hole 6 434 yards par 4

Brian Gaffney, head pro at Quaker Ridge, has some solid advice for bogey golfers—and everyone else—faced with the innocent-looking sixth hole. “The trick to playing this hole is to do it very carefully,” he says. “It’s most important to keep the ball in play off the tee because there’s a creek down the left side and rough on a steep hillside on the right. If you can get your ball into the fairway, the next challenge is to avoid the two bunkers that guard the left and right side of the hole on your second shot.” That’s where laying up might not be a bad idea. “If you can get past them in two, you should have a high percentage shot onto the green,” Gaffney says. “Of course, then you have to putt on that green. It’s amazing; it’s such an incredible design from 100 years ago. You can still one-putt for a par if you stay below the hole.”

Hudson National Golf Club

Hole 14 530 yards par 5

Hudson National head pro Mark Parisi says the 14th hole is his personal favorite and shouldn’t give a bogey golfer too much trouble as long as they play it with respect. “Par is possible with three solid shots,” he points out. “The tee shot is very open and friendly, but on your second shot, water is in play on the right and heavy rough on the left.” The second shot is also menaced by a bunker and long, heavy rough if you try to cut distance off the dogleg. Safety should be your byword, according to Parisi. “Aim toward the larger portions of the fairway and lay-up zones, and just accept the fact you’re hitting a mid-iron into the green instead of taking chances to get a wedge in your hand or going for the green in two by cutting over the lake.”

Wykagyl Country Club

Hole 7 171 yards par 3

One of the county’s most challenging par threes, Wykagyl’s seventh hole has a severely sloped green from back left to front right. Multiple bunkers surround the hole, and play from the tee is over a deep, intimidating valley. Head pro Ben Hoffhine says par is possible, even for the bogey golfer. “Hitting the green is a big plus, but any tee shot right of the green still gives the golfer an opportunity to make three,” he says. “Any kind of chip, pitch, or bunker shot from the left will be nearly impossible to keep on the green. Because of the severe slope, from a strategic standpoint, it is always better to be right so your second shot is uphill.” Hoffhine recommends managing your expectations. “Wykagyl is unique in that it has five par-three holes,” he says. “If a bogey golfer can walk away from them with five bogeys, they will have a good chance of posting a good score.”

Century Country Club

Hole 5 435 yards par 4

Subtle difficulties plague the bogey golfer on the fifth hole at Century. The fairway is wide and inviting, but there’s more to your tee shot than staying out of the huge bunkers on the right. A Japanese red maple tree in the distance serves as the ideal target line. A drive just to the right of that is perfect, but anything to the left will leave a long, tricky approach. Head pro Nelson Long advises, “Keep your approach shot to the left side of the green, because it all slopes to the right.” He’s correct, of course, but it’s a long shot for most of us, and there’s little room for error. Your second shot plays downhill, but a swale in front of the green will stop players hoping to sneak a runner onto the green. Whether you’re pitching, chipping, or putting your third shot, remember what Long said: “It all slopes to the right.”

Winged Foot Golf Club West

Hole 17 435 yards par 4 

“It’s best to favor the left side of the fairway off the tee,” says head pro Mike Gilmore. “The right side has bunkers and trees.” The fairway on the 17th hole isn’t wide, though, so straight is good, especially for a bogey golfer who doesn’t want to try to hit a perfect three-wood out of the rough on his second shot. The real test on the hole comes with the approach, though. Gilmore points out, “The green is very narrow for a long hole and has bunkers on both sides. Missing it pin high is a very tough up and down.” Gilmore suggests playing it smart may be the bogey golfer’s best chance for a small number. “To ensure no worse than bogey, it may be best to hit your approach shot just to the front of the green.” That leaves you with a straightforward and generally uphill chip.

Anglebrook Golf Club 

Hole 4 582 yards par 5

The fourth hole at Anglebrook is simply one of the toughest par fives you’ll ever play. It starts with an imposing view from elevated, tabletop tee boxes, where you see not only a wide fairway but an environmental area to carry, OB right, another environmental area left, and a huge bunker squeezing the landing area. As head pro Rob Davis points out, “It demands two near-perfect shots to even be in the position to reach the green in regulation. Even then, you’ll have about 140 yards in to a green with a pond in front, environmental area on the left, bunkers right—and an enormous, triple-tiered, treacherous green. There is no safety on this hole until the ball is rattling around in the jar.”

Davis believes a bogey golfer should play this hole for a six and not be disappointed with a double. “The scoring average, including those seeing the hole for the first time, is probably 8.5,” he says. “Bogey feels like par. Few players know what birdie feels like.”

More: The Best 18 Holes In Westchester

GlenArbor Golf Club

Hole 7 206 yards par 3

Regardless of whether you play the seventh hole at GlenArbor from the blue (206 yards) or white (173 yards) tee, the key to avoiding a big number on this demanding par three is to stay below the hole off the tee, according to Director of Golf Rob Labritz. “The green is canted strongly from back to front,” he points out. “And if you get above it or to the left, you’re basically looking at a double at the best.” The fairway has a nice wide landing area in front of the green and the bunkers, though, so a good strategy is to play for that spot instead of the putting surface, chip on, and putt for your par or at worst a bogey. “Remember, the hole plays 10 yards downhill, so hit the club that leaves you short of the hole and the bunkers.”

Leewood Golf Club

Hole 15 464 yards par 4

The 15th at Leewood plays as a par five from the white tees and a long, long par four from the blues. Regardless of the tees you play, there isn’t an easy shot on the hole. The fairway slopes left to right and bunkers dot the right rough, so keeping the ball on the short grass is tough if you have any fade on your drives. Once you get on the elevated green, either in two (not likely) or three strokes, you’ll be faced with a roller coaster of split tiers with big slopes back to front and from left to right. This is the No. 1 handicap hole at Leewood for a number of solid reasons.

Metropolis Country Club

Hole 6 406 yards par 4

The sixth hole at Metropolis is a perennial favorite of Westchester golfers. It is a picture-perfect dogleg left with a fairway sloping from right to left and a small pond short and right of the green. Recent renovations made a great hole even better. Head pro Craig Thomas says the way to play it is to aim for the fairway bunker from the tee. “This will allow the ball to kick toward the middle of the fairway and toward the green,” he explains. “A ball played down the middle or to the left side of the fairway will have an obstructed view of the green and cause the player to lay up for their second shot.”

 The bogey golfer has a tough decision to make on the second shot. Thomas says, “You can go for the green, and in doing so bring both the water hazard as well as the bunker directly fronting the green into play, or lay up safely taking both the bunker and water out of play.” Regardless of your decision, he says, “Choose your club wisely as it is imperative to land on the correct tier of this difficult green. If the pin is located on the upper, rear tier of the green, be careful not to hit over the green, since doing so will guarantee not getting up and down.” 

Old Oaks Country Club

Hole 5 417 yards par 4

Managing your aim is key to scoring on this long, difficult dogleg right. Take care on the tee because the box doesn’t point to the center of the fairway but rather toward the trees on the right, which is not a place you want to go. The perfect drive is to the right center of the fairway, where you will be left with a hybrid or long iron to the green. Again, aim is critical because the green is flanked by bunkers on both sides. Playing short of the green takes the sand out of play and leaves a manageable chip to the slick and challenging putting surface.

Trump National Golf Club Westchester

Hole 12 530 yards par 5

One of the most intimidating par fives in Westchester is the 12th hole at Trump National in Briarcliff. It’s not overly long, but the green sits behind a seemingly bottomless canyon, and there’s no place to miss your approach shot right or left, either. The drive is straightforward (although a lateral hazard runs the entire length of the hole on the left), and few bogey golfers are going to try to reach the green in two; so the question really is how far back to lay up for your third shot. The answer is the distance where you have the most confidence. If your favorite club is a 140-yard eight iron, lay up to there. If you’re not afraid of a half wedge, go nearer to the chasm and pitch over it to snuggle one up to the pin. 

Whippoorwill Club

Hole 5 455 yards par 4

Whippoorwill is a course that begins easy but toughens up with a vengeance when you reach the fifth hole, a long par four that proves once again that choosing the right tees is essential to enjoy a round of golf. From the blue tees, this hole requires a 250-yard drive to get over the hill and give you a somewhat reasonable second shot to the elevated green. Woods line the fairway on both sides, and the ones on the right are actually a lateral hazard; so if you tend to slice when overswinging like most of us do, seriously consider moving up to the white tee box. Even from there, the bogey golfer will probably be left with a second shot that should be a layup to the steeply elevated green. Rely on good wedge play, not brute strength, to eliminate the chance of a big number.

Willow Ridge Country Club

Hole 4 210 yards par 3

Head pro John Reeves says the fourth hole at Willow Ridge has all of the elements to raise the heart rate of a scratch golfer and can be downright overwhelming for the bogey golfer. “It starts with the uphill 210 yards to the green that plays more like 225,” he says. “The green is guarded with bunkers left, right, and long, although the back bunker serves as trouble not so much on the tee shot as for second shots that are struck too thin.” He points out that a miss of more than 25 yards left or right of the green means you’ll be hitting three from the tee because your ball is lost or out of bounds. Reeves adds: “Most bogey golfers want to attack a par three like they see the tour players do on TV. The best strategy for this hole is to play the tee shot short of the green. The fairway approach starts approximately 60 yards from the green, so you will have a second shot from the short grass with no bunker to carry.” Take care once you’re on the green, though, because the green is severely yet unnoticeably sloped from back to front. He cautions, “Putting from above the hole leads to three- or even four-putts.” 

Fenway Golf Club 

Hole 9 400 yards par 4

Heath Wassem, head pro at Fenway, pulls no punches when asked why bogey golfers have trouble on the ninth hole. “It is tough,” he says, “especially for the average player because the second shot plays so long uphill. That’s typical for Fenway, which is probably the longest-playing short-yardage course in the county.” The tee shot isn’t particularly challenging, he says, but “hitting up into that green makes the hole play at least 15 yards longer than the yardage on the scorecard. For the bogey golfer who wants to stay away from the bunkering, the smart play is left and short of the green to leave a 50-yard wedge onto the green. From there you can two-putt and get out of there.”

How We Choose

By our calculation, there are about 900 golf holes on 49 courses in Westchester County. How, then, did we choose 18 of them to feature? By playing them, of course! Our panel of players visits as many courses as we can during the course of the golf season. This year, thanks to the hospitality of the members and staff of Westchester’s golf clubs, we visited 42 public and private courses. At each one, we talked to the club pros about their favorite holes and why they like them. Finally, after much debate, we selected 18 holes to feature. 

Our panel of players: Dan Berger, Rye Brook; Ned Branthover, Bronxville; Craig Burrows, Yonkers; Casey Egan, White Plains; Tim Finneran, Crestwood; Alan Kalter, Stamford, Connecticut; Bill Losapio, Valhalla; Joe Miressi, New Rochelle; Ken Nilsen, Mount Kisco; Kelly Parkhurst, Darien, Connecticut; Thomas Ralph, Pelham; Bruce Schoenberg, Hastings-on-Hudson; Robert Westenberg, Bedford; Gene Westmoreland, Bronxville; Ralph Wimbish, Mount Vernon; and John Zanzarella, Ossining. Westchester/Hudson Valley Magazine Publisher Ralph Martinelli often led the troops during this arduous (but fun) campaign.

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