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18 Hard Golf Holes in Westchester

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Ahab had his white whale, Galahad the Holy Grail, but Westchester golfers have impossible quests of their own: par on some of the hardest golf holes anywhere. It seems like every course has at least one hole that beats you every time you tee it up. It might be a hazard-lined dogleg par four or a par five with a green the size of a ping-pong table. Or maybe your personal bugaboo is that innocent-looking par three where a gust of wind seems to push your tee shot into bogey territory every time you play it.

The pros aren’t immune, you know. They have their own problems with particular holes on their home courses. We asked the head pros at all the clubs in the county to identify the toughest par — for them — on their home course. Very few chose a par five. As you would expect, these power-drivers will generally reach them in regulation without too much trouble. What was surprising, however, was how many chose a par three. The one-shotters, it seems, especially those with little or no margin for error, bedevil even the guys who play this game for a living.

When we picked the 18 hardest holes identified by the pros, we came up with a 7,251-yard, par-70 monster course where every tee shot demands perfection and every putt can terrify par right off your scorecard.

1. Trump National Golf Club Westchester

Briarcliff Manor • Hole 3 • 455 yards  • Par 4

Patrick langan: “Even if you hit a good tee shot, there is a lot that can go wrong on this hole. There is water left all the way to the green, and deep-faced bunkers on the right. It’s also one of the smaller greens on the course. Even a good player is coming in with a long iron or hybrid. I’d actually call this a par 4.5.”

2. The Apawamis Club

Rye • Hole 7 • 409 yards • Par 4

James Ondo: “This is a very tough driving hole. You really have to be on the spot to make your second shot work. It’s blind and has to go through a chute of trees to a very small green that actually slopes away from you, so you don’t want to be hitting a long club into the green if you can help it. That’s why the drive is so important. It has to be long enough to leave a controllable second shot and in the right place in the fairway to have a good line.”

3. Bedford Golf & Tennis Club

Bedford • Hole 3 • 200 yards • Par 3

Steven Dougan: “It’s a tough green to hit, then once you get there, it’s a very tough green to putt because it’s a big green with a lot of movement. As it happens, there aren’t a lot of possible hole locations because the green is so severe in spots. It’s definitely a challenge.” 

4. Knollwood Country Club

Elmsford • Hole 18 • 464 yards • Par 4

Bob Miller: “The restoration of this hole has made it once again probably the hardest finishing hole in Westchester. The tee box has been moved back about 25 yards, which brings the lateral hazard on the right side even more into play. You have to hug that side, though, because if you go too far left, you’ve got a long, long second shot into the green. We also restored some bunkers where there used to be bailout areas.”

5. Westchester Hills Golf Club

White Plains • Hole 6 • 529 yards • Par 5

Jason Gobleck: “There’s trouble everywhere on this hole. Water is in play on the second and third shot. Out of bounds comes into play, too. The tee shot is blind as well, which always adds a little bit of tension to the swing. Even on the layup, there is some thick rough that will snag you if you don’t find the fairway. That makes the hole harder and harder. Even the long hitter who goes for the green in two can easily find himself making a bogey. The average golfer who plays it as a three-shot hole has to contend with the water. The green is tough, too. You have to put your ball in the right section of the green if you want to have a decent two-putt.”  

6. Winged Foot Golf Club West

Mamaroneck • Hole 1 • 450 yards • Par 4

Mike Gilmore: “Our opening hole is long and the green is brutal. If you can two-putt that green, you’re off to a great start. It’s hard enough getting there — you’ve got a long poke to begin with. Then you have all you can do just to keep it on the green. Above the hole is impossible.”

Winged Food Golf Club West

7. Mount Kisco Country Club

Mount Kisco • Hole 16 • 466 yards • Par 4

Chris Case: “This is a standout hole. You have to draw your tee shot to have a good shot at the green. Even then, you’re not going to have a level lie for your approach. The green is huge, so there are a lot of different challenges depending on the pin placement each day. It’s hard, but probably my favorite hole on the course.”

8. Pelham Country Club

Pelham Manor • Hole 2 • 217 yards • Par 3

Mike Diffley: “At 217 yards from the back tee and even 205 from the whites, this is a long shot. Even the best players have a hard time hitting that green, which is sort of a Redan that runs from front to back. Worst of all, there’s no ‘miss.’ Hit it right and you’re maybe in for a double; miss it left and you’re in deep, deep bunkers. If you’re in them, you just hope to get out, much less try to get close to the hole. Short means your ball will probably kick left, leaving a tough chip even if you stay out of the bunkers. The second problem is, it’s early in the round for such a precise shot. It always seems to play a little easier if you’re in a shotgun start where you don’t face it right away.”

9. Hudson National Golf Club

Croton-on-Hudson • Hole 15 • 427 yards • Par 4

Theron Harvey: “Our 15th hole gets overlooked sometimes, but, for starters, it’s a 443-yard par four — which should get anybody’s attention. We added a bunker on the left side of the fairway, so there’s no place to bail out from the tee. It’s either fairway, fescue, or a bunker where the landing area pinches in. From there, your sight line is partially blocked by a rock ledge on the right, then there are bunkers that cut across the fairway as you look uphill to the green. The green from that angle has an ‘infinity’ look to it. It’s also a smaller green that slopes right-to-left big time. It looks flat, but it’s one of the most deceiving greens out there. It’s very fast and breaks a good foot and a half more than you think.”

10. Hollow Brook Golf Club

Cortlandt Manor • Hole 7 • 442 yards • Par 4

Philip Eyre: “Even off the forward tees, the carry to the fairway over the wetlands area may be only 185 yards, but it is very intimidating. It’s the second shot that always gets me, though. Players don’t recognize that the bunker in front of the green cuts into it quite a bit. You’ve got a mid- to long-iron that has to get over it, too. That bunker is a killer. It’s at least 10 feet deep. It’s so punishing, in fact, it reminds me of the Road Hole bunker at Saint Andrew’s.”

11. Hampshire Country Club

Mamaroneck • Hole 9 • 216 yards • Par 3

Rob Sutton: “This par three plays longer than the yardage because the green is elevated. It’s also protected by bunkers, and there’s only a small throat to run up a shot if you play it that way. Even if you’re on the green in regulation, it’s still not over — a 20-foot putt can have five feet of break.”

Hampshire Country Club

12. GlenArbor Golf Club

Bedford Hills • Hole 12 • 579 yards • Par 5

Brian Crowell “Length is not always a true indicator of difficulty, but our longest hole is the most challenging par five at GlenArbor. Number 12 stretches to 579 yards from the blue tees and is reachable for only the biggest of hitters. The hole bends to the right, then back to the left, rewarding a power fade off the tee and then a draw for the second shot. The need to ‘work the ball both ways’ makes this a true test — and we haven’t even discussed the green complex yet. The putting surface is deep, but very narrow, and demands an accurate approach. The green features three distinct tiers: low landing areas in the front and back, with a raised plateau in the middle. The undulating green is surrounded by deep bunkers on three sides. This hole requires concentration and three well-placed shots to have any chance at a birdie. It’s a solid hole, even for those in the ‘Championship Flight.’ ”

13. The Saint Andrew’s Golf Club

Hastings-on-Hudson • Hole 8 • 422 yards • Par 4

Charlie Hicks: “You have to watch your alignment and guard against misdirection off the tee, but the real trouble comes on the approach. The green is 45 yards deep and has a false front, a middle depression, and a back tier. There can be as much as a four-club difference front to back. The green is deep but rather narrow, so you need to be aware of the four greenside bunkers lurking right. The scratch player will make his share of bogeys here.”

14. Sunningdale Country Club

Scarsdale • Hole 13 • 455 yards • Par 4

Chris Toulson: “Several things make this a tough hole. For one, it’s uphill. For another, it’s long — 455 yards from the back tee. It’s also a pretty tight driving hole, with out-of-bounds right and trees left. The fairway has huge hummocks that can deflect your drive, and it slopes a bit from left to right. For the longer player, there is a little speed slot on the left side, which helps if you can hit it. The green has a pretty severe back-to-front tilt so you can have a tremendous amount of break once you get there.”

15. Waccabuc Country Club

Waccabuc • Hole 9 • 227 yards • Par 3

Martin Granda: “This is a very difficult, very long par three. Every shot has to be good. If you miss the green from the tee, you have to be short because it’s a hard up-and-down from anywhere besides the fairway. The green has a lot of movement on it, too — more than you think!”

16. Westchester Country Club West

Rye • Hole 17 • 443 yards • Par 4

John Kennedy: “All the shots you take on this hole must be played correctly to make a par. The tee shot has to go at least 255 yards from the back tee to clear the corner of the dogleg. That still leaves 180 yards over water to reach the green — and your second shot also has to be accurately placed between the greenside bunkers. Then there are the putts. The green has two tiers and is very fast back to front, so two putts are never assured.”

17. Brae Burn Country Club

Purchase • Hole 17 • 410 yards • Par 4

Nick Yaun: “It’s one of the longer par fours on the golf course, but our 17th hole has a tiny landing area you have to hit from the tee. Your drive should work right to left in order to hold the fairway, too. You also have to look out for ‘Wilt,’ the lone tall tree on the left that’s named after Wilt Chamberlain because of its ability to swat balls out of the air. The approach shot is strongly uphill — generally over 200 yards — to a green that’s guarded on both sides by deep bunkers. When you come to the tee, hold on tight. If you can squeak through this hole, your last one is a par five and you can breathe a little sigh of relief.”

Anglebrook Golf Club

18. Anglebrook Golf Club

Lincolndale • Hole 18 • 440 yards • Par 4

Rob Davis: “Our finishing hole has the potential to be a real round-buster and generates a lot of controversy. The real sting comes from a gut-wrenching choice of what to do off the tee. Trent Jones Sr. added a big bunker smack-dab in the middle of the fairway, so you have to choose a strategy. If you have the accuracy, you can hug the left side as long as you don’t overwork your draw and put the ball into the environmentally sensitive hazard. If you have the length, you can drop a driver over the top of the bunker into a short and abrupt landing area and shave some yardage off your approach. Your third choice is the smart one: Keep your ego in check, and lay your drive out to the right of the bunker or even lay up short of it. Remember, though: The hole plays longer than its yardage since the final 100 yards are subtly uphill, so it plays like a mini par five. If you navigate the bunker, you still have to deal with the green. It’s practically blind, with severe undulation in the front pocket and left side. Deep bunkers guard the left and right side of the front of the green, leaving a very narrow uphill alleyway to try to chase your long approach through.”


Nine More Round-Wreckers

Sleepy Hollow Country Club

Hole 11 433 yards Par 4

David Young: “This is a long hole and it plays left to right, which is why lefty Bob Charles used to love it when the Senior PGA played here — he could just hook it around the corner. The second shot is to an elevated green with deep bunkers on both sides.” 

Elmwood Country Club

Hole 13 200 yards Par 3

Pete Stefanchik: “Number 13 at Elmwood can play up to 200 yards long, but is challenging enough from the 172-yard white tees. Even if you hit the green, you have to hope that it holds because there’s no room long, two deep bunkers left, and a 40-yard-long bunker right. Par from the sand is definitely challenging.”

Willow Ridge Country Club

Hole 4 210 yards Par 3

John Reeves: “This long par three leaves no room for recovery from a slight mistake off the tee. It not only measures long, but it’s steeply uphill, so it plays about 220 regardless of what the yardage is on the scorecard. The green is very small and protected by bunkers. It also slopes from back to front, so if you somehow power your tee shot over the green, you have an impossible recovery shot.”

Ardsley Country Club

Hole 16 446 yards Par 4

Jim Bender: “The driving area on this dogleg right is very narrow, and the shot is uphill. If you don’t hit a perfect drive and end up a little short and right of center, you won’t have any shot at the green except a big, big fade. Even if you hit a good drive, you’re hitting 180 or 190 for the second shot.”

Bonnie Briar Country Club

Hole 17 470 yards Par 5

Frank Mattei: “Our new 17th hole took away an easy birdie and added some teeth to the golf course. The problem is the elevation of the green and the false front, which will kill you. Then there’s the natural canopy of the trees on either side of the fairway. They didn’t used to be a problem with the old green, but now your approach has to reach its apex near the tops of the trees in order to land soft on the new green.”

Brynwood Golf & Country Club

Hole 5 441 yards Par 4

Michael Mercadante: “Nothing works for you on this hole. You hit from an elevated tee to a dogleg right, but the fairway slopes left. The fairway undulates, too, so you never have a level lie. Your second shot is most likely about 200 yards off a hook lie where you can’t miss left. Not a good combination.”

Scarsdale Golf Club

Hole 7 430 yards Par 4

Bill Smittle: “Even in the better-ball format of the Wilson Cup, our seventh hole plays over par. There is a narrow landing area with a lot of undulation. Then the green sits above the fairway a bit, so the second shot is tough since you can’t really roll the ball up onto the green. A lot of scratch players make bogeys there, too.”

Salem Golf Club

Hole 16 443 yards Par 4

Charlie Poole: “The hole is not really, really long, but it’s long enough. There is water all along the right side. It looks wide open, but if you don’t cut the water off with your drive, you’re left with 210 yards to the green for a second shot at an uncomfortable approach angle. There’s a lot of slope to that green, too.”

Fenway Golf Club

Hole 12 454 yards Par 4

Heath Wassem: “A demanding tee shot requires right-to-left shape with a fairway that slopes in the opposite direction. Even if you find the fairway, the second shot is into a deceivingly narrow green. Both sides slope towards extremely deep bunkers, effectively only giving you a 12-yard landing area for safety. If your ball rolls into the bunkers, the odds of an up-and-down are not in your favor.” 

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