Here’s How Golf Pros Would Tackle Westchester’s Most Challenging Courses

Saint Andrew’s Golf Club, Hole 2
Photos by John Fortunato

Golf is the most mental of all sports. Sure, there are strategic and tactical decisions made all the time in football, baseball, and hockey, but success in those games depends heavily on split-second moves made in almost automatic response to an opponent’s play. In golf, we stop and ponder every single move. We reflect.

We think… about the wind, the grass, the distance, the humidity, the curve of the Earth and the direction of the sun. And our stance, our grip, our backswing, posture, pronation, dominant eye, clubhead path, angle of descent, ascent, and repose. We visualize what we hope our ball will do and try to answer a hundred questions before honing them down to a single swing thought.

We play the game in our heads but compete on the golf course, where every hole is a strategic challenge. Our composite course for 2020 includes some of the best mental tests of golf in Westchester. The 18 holes make up a course measuring 6,673 yards, par 72, which sounds pretty short and easy. Every hole, though, is like a chess problem with a dozen solutions. To help us find the answers, we asked the pros how they would think their way around our course.

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– 1 –
St. Andrews
Hole 2 325 yards par 4

Head pro Greg Bisconti immediately identified the second hole at St. Andrew’s as a good hole that requires thought. “Although it’s a short par 4 that is potentially reachable off the tee, you have to decide if it is worth the risk. There are penalty areas left and long and the closer you get to the green, the trickier the pitch becomes.

You’ll have a downhill lie to an elevated green that has a swale in the left-center ready to catch any shot that does not have the required spin to control the ball. The more prudent play is to hit a shot no more than 210 yards off the tee and leave yourself a full 90 to 110 yards into the green. This way you are able to hit a full shot and control the spin and thus the ball as it hits the green.”

– 2 –
Apawamis Club
Hole 16 186 yards par 3

The final par 3 at Apawamis can give you plenty of need for “Consolation,” as its name on the scorecard appears. It’s long, plays uphill, and is surrounded by trouble. The green is also small and has a nasty false front that’s particularly narrow, so your tee shot needs to carry the full distance to the center of the green. But no farther! Anything off the back will lead to a big number on your card.


Hollow Brook Golf Club, Hole 11

– 3 –
Hollow Brook
Hole 11 420 yards par 4

Watch the wind and use your head when you tee it up on the number-one handicap hole at Hollow Brook, says head pro Phil Eyre. “Being in the fairway off the tee is key,” he says. “You can be aggressive with the driver and hold it tight to the waste area on the left to get a nice, flat lie, leaving you about 140 yards into the three-tier green. Or you can make a more conservative play, with a three or five wood, laying it back to about 180 on a flat lie. If you hit between those two distances, you have an awkward hook lie, with the ball above your feet, something you really don’t want going into that green with water on the left. For the second shot, the ideal play is to the middle of the green, maybe a bit to the right side. It’s narrow, and there’s a lot of trouble all around.”

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– 4 –
Anglebrook Golf Club
Hole 2 521 yards par 5

Relatively short par 5s make great risk-and-reward holes, as the downhill second hole at Angelbrook perfectly demonstrates. An aggressive driver of the ball can carry the cross bunker that cuts into the fairway. That fearless play sets up a long but doable second shot into the green. The other option is to lay up right of the bunker and plan on making your birdie with your wedge after a conservative second shot. Either way, your approach shot has to stay away from the hazard on the left and the bunkers on the right that guard the narrow opening to the green.

Whipporwill Club, Hole 13

– 5 –
Whipporwill Club
Hole 13 320 yards par 4

Think backward from green to tee on the testy 13th hole at Whipporwill, says head pro Jim Wahl. “The most important thing off the tee is to leave yourself with a full wedge or sand wedge into the green,” he advises. “It’s about a 200-yard shot to the upper part of the fairway, and there is a fairly generous landing area. If you hit it too far toward the green, you’re left with an awkward pitch because the green is above you, and you can’t see the cup, which makes distance control with a half-swing very difficult. I like to keep the ball to the right-center of the fairway, because you get a flatter lie and avoid the fairway bunkers on the left.”

– 6 –
Brae Burn Country Club
Hole 8 190 yards par 3

The 8th hole at Brae Burn is pretty — pretty deadly, that is. It features a forced carry over water to the green; there are bunkers on both sides; and the green slopes heavily front to back, so any ball long leaves you with an impossible downhill recovery shot. Asked about the hole, head pro Nick Yaun says, “There’s nothing but trouble on this hole. Quite a few members lay up, and that’s not just the short hitters. If you’re a little wild, it’s not a bad play. It leaves you a good chance for a three, or at worst a four, and avoids the penalty strokes that kill your score.”

Salem Golf Club, Hole 14

– 7 –
Salem Golf Club
Hole 14 595 yards par 5

Scoring a par on the longest hole at Salem all boils down to one thing: the tree on the corner. The quandary on your second shot is, do you go short of it and try to cut left or right of it, or do you try to go over it? The idea is to hit your second to a place where you can still reach the green with your third shot. There is water on the way to the green, so you may have to lay up and use your fourth shot to get on the green. If your drive isn’t in the right spot, the tree becomes an even bigger deal.

– 8 –
GlenArbor Golf Club
Hole 2 428 yards par 4

Decisions, decisions! This dogleg left offers the tantalizing prospect of cutting the corner with a high draw off the tee — although there’s little or no room for error and an overcooked hook will bring disaster among the trees. The safer play is a fairway wood or hybrid straight off the tee and short of the fairway bunkers. You’ll still have a short iron or wedge into the green.

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Hudson National Golf Club, Hole 5

– 9 –
Hudson National Golf Club
Hole 5 412 yards par 4

“Number five is a transitional hole that plays from the highest point on the golf course down to the lower points,” says general manager Theron Harvey. “Your strategy depends on the tee box you’re playing. When you use the elevated boxes on the left, you’re really hitting downhill to the fairway, so you’ll want to use a hybrid or a long iron. When you go back to the newer tee boxes, it’s more of a level dogleg left to right, so you’ll probably hit a driver or fairway wood toward the bunker. There’s fescue on the left, and the right side kicks hard away from the fairway, which looks tiny anyway when you’re playing at eye level. You’ve really got to trust your tee shot and put something in the fairway.”

– 10 –
Mount Kisco Country Club
Hole 15 376 yards par 4

Shot shapers love the 15th hole at Mount Kisco, although the “risk” in risk-and-reward comes into play for those whose judgment is off that day. A solid draw off the tee can clear the fairway bunker on the dogleg, but too much curve on the shot will carry your ball into oblivion. Straight shooters will want to hit less than driver to avoid going through the fairway, but even a short tee shot will leave an easy iron into the green.

Old Oaks County Club, Hole 8

– 11 –
Old Oaks Country Club
Hole 8 430 yards par 4

What looks like a benign, straightforward par 4 is actually the devilishly difficult number-one handicap hole at Old Oaks. Head pro Nick Maselli explains the dichotomy: “Number eight plays uphill and really begins with the second shot. Most amateur players are hitting a fairway wood into the green. Playing it like a par 5 is not a bad idea. When you lay up, you have to make a decision as to whether you’re going to pitch it up with a lob wedge or hit a little runner into the upslope on the green. It all depends on the hole location. A front hole location is a little easier. A back pin, though, makes both shots a little more difficult because you have to hit it into the front tier and let it roll up the hill and get it to stop with a bump and run. The pitch is delicate, too. If you carry it too far, it’s gone, and if it’s short, it will roll right back to you.”

– 12 –
Century Country Club
Hole 17 221 yards par 3

Plenty of mid-handicap players use a driver on Century’s penultimate hole, one of the longest par 3s in the county. It’s really a leap of faith, though, to believe you can stop the ball on the green if you need a driver to get there. Depending on the pin position, wind, and the vagaries of their swing, the thinking player may opt to lay up to their favorite wedge distance or even aim for the right side alley to the green, where they can bump their second shot to the cup.

Sleepy Hollow Country Club, Hole 12

– 13 –
Sleepy Hollow Country Club
Hole 12 536 yards par 5

What looks like a simple par 5 is much more complex than you think, according to head pro David Young. “There are three ways to play this interesting par 5,” he says. “If you’ve hit a good drive, you can always go for the green in two. It’s elevated, though, and the green itself has a couple of shelves, so you will want to make sure of the pin position if you want to get close. The second option, hitting your second shot short of the creek, will have much less risk. It’s a big green, so again, check the pin position to decide what distance you want to leave for your approach. Finally, many players don’t realize there is a lay-up area left of the creek, which gives a good angle to the green for your third shot.”

– 14 –
Scarsdale Golf Club
Hole 9 325 yards par 4

Can you say “distance control,” boys and girls? Regardless of whether you choose to boom one over the water to the front of the green or play it safe with a straight shot to a conservative iron distance, you’ll need to make your tee shot stop in the right place to avoid the bunkers right and water left on this short hole at the turn at Scarsdale.

– 15 –
Hole 5 355 yards par 4

It’s remarkable how crucial the pin position is on the short 5th hole at Sunningdale. The newly remodeled green has three small lobes and can only be held with a high, soft approach shot. Depending on which lobe has the cup, you may need to place your tee shot left, right, close, or farther away from the green to set up your pin-point approach.

Westchester Country Club West, Hole 10

– 16 –
Westchester Country Club West
Hole 10 180 yards par 3

Number 10 looks so simple, but it’s so, so hard. Teaching pro Sarah Stone says, “It’s a great par 3. You’re going to be using a longer club, like a mid-iron or a hybrid. There’s out of bounds on the right and bunkers on either side, so you have to hit your favorite club like a laser to the middle of the green. You can’t really go at any pin, either, because the green structure is very challenging. Your ball can roll off the green left or right, and rolling long is death in the run-off collection area in the back. I often encourage players to take one less club and plan to putt from off the green.”

– 17 –
Siwanoy Country Club
Hole 8 340 yards par 4

Without a solid game plan, whatever can go wrong, will go wrong on the 8th hole at Siwanoy. Blasting a testosterone-fueled driver off the tee is fun, but that idea will probably leave you hitting your approach shot off a severe downslope into an elevated green, which isn’t fun at all. Even with a level lie for your second shot, be careful about pin-seeking, especially if the cup is cut near the edges of the green, where it usually is. A slight miss can send your ball into bogey territory in a heartbeat.

Wykagyl Country Club, Hole 10

– 18 –
Wykagyl Country Club
Hole 10 513 yards par 5

How can such a short par 5 be rated as the number-two handicap hole at a course as complex as Wykagyl? The answer is simple, according to head pro John Deigan. “A good drive sets up the possibility of reaching this green in two,” he says, “but you must avoid the bunkers left of the elevated green at all costs. They’re deep and don’t leave you much green to work with. The safer strategy is to lay back to your favorite wedge distance on the second shot. Be sure to check the pin position on the deep, three-tier green, though, before you choose the club for that crucial third shot.”

Westchester’s Brain Game Scorecard

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