How to Play Your Best on the Best Golf Course Holes in Westchester

GlenArbor GC hole 4. Photos by John Fortunato

How do you score on the best holes in Westchester County? We asked the experts who know just how to approach them.

Golf requires multiple skills, both mental and physical. The wonderful courses in Westchester call for them all, so we chose 18 holes to make up a Skills Tester Course that demonstrates the full gamut of techniques you’d need, then asked the PGA pros who play those holes for a living how to put a par or better on your scorecard.


Fenway GC #18
512 yards // Par 5

Our round starts with making choices — hopefully smart ones. The uphill finishing hole at Fenway brings water, sand, and out-of-bounds into play, so the first step to scoring par is to engage your brain. “If you hit a good tee shot, you can go for the green in two,” says head pro Tyler Jaramillo, “but it’s a hard ‘go-for-it’ because the green has out-of-bounds all around, and you’re probably not hitting off a level lie. The tee shot doesn’t need to be long, but it must be straight, because there are deep bunkers on the left and the creek on the right. If you lay up off the tee to the bottom of the road, though, and then lay up short of the road at the top of the hill, you’ve got an easy 120-yard shot to the green.”

- Advertisement -


GlenArbor GC #4
Bedford Hills
415 yards // Par 4

The drive determines your likely success on the #1 handicap hole at GlenArbor. Long matters a lot, but straight may matter more, since there’s trouble both left and right. Head pro David Gagnon says the most important step is the first one you take, walking up to the tee box. That’s when you should mentally visualize a positive picture of a long, straight drive. “Then just let go,” he says. “Forget all those technical swing thoughts and swing free.”

Pound Ridge Hole 2
Pound Ridge GC, Hole 2


Bonnie Briar CC #11
453 yards // Par 4

This dogleg right may play downhill, but it’s still a long, long journey from tee to green. The best line to the green is from the right side of the fairway, but beware the bunker just off the short grass that’s within reach of a solid drive. The second shot is long, too (and blind, to boot), but at least the green isn’t surrounded by sand. Check your approach line before you swing and aim for the left side of the green, which tilts right.


Century CC #13
140 yards // Par 3

- Partner Content -

“Just don’t think about the water,” says head pro Nelson Long, who retired from Century last year after nearly five decades at the club. “It’s a short hole without a lot of depth to the green, so pick the right club for the distance, relax your grip, and take a couple of practice swings to build a smooth tempo.” Long’s buttery-smooth swing is a great one to emulate — it qualified him to play in two USGA championships, 45 years apart: the U.S. Junior in 1968 and the U.S. Senior Open in 2013.

golf green
GlenArbor GC Hole 4


Anglebrook GC #13
582 yards // Par 5

It may be one of the most intimidating par fives in the county, but head pro AJ Berglund says par is very, very possible. “It’s all about giving yourself the best third shot,” he says. “Off the tee, you have more room to the right than you think, and your ball will funnel left to the center of the fairway on both your tee shot and second shot. The second shot is really the key. With a good one down to the flat before the water, you’ve got a much better chance at putting the ball on the proper tier on the huge green. People get scared by the length of the hole, but it’s not a hard par if you play it smart.”


Wykagyl CC #15
New Rochelle
341 yards // Par 4

“The 15th hole at Wykagyl may be short, but it is no walk in the park,” says director of instruction Anna Ausanio. “When I step onto the tee, I play a conservative shot, using either a hybrid or fairway wood to give me comfortable yardage to the green. My most crucial move while making that swing is to allow my arms to start first from the top of the backswing back down to the ball. This produces a nice, high, baby draw. My worst mistake is trying to overpower my shot and not being patient, causing me to come over the top.” She points out that the hole’s green is very tricky, too, with multiple tiers and a false front, so choose a layup distance where you can hit a wedge you believe in.

- Advertisement -


Pelham CC #2
210 yards // Par 3

One of the finest par 3s in Westchester, Pelham’s second hole gives you a lot to think about on the tee box, but proper club selection is absolutely paramount. The hole is long but plays downhill. The green is large, but so is the bunker guarding it on the left. Long and right may be safe, but you’ll be left with a dangerous flop shot from a downhill lie in long rough to a green that’s sloping away from you. Short is safe only if your ball lands in a narrow flat on the right front of the green, otherwise it may well slide down to the bunker. So pick the right club and aim for the center of the green.


Knollwood CC #6
432 yards // Par 4

The #1 handicap hole at Knollwood is named Tribulation for more than one reason. The tee shot needs to land in the left half of the fairway to avoid being blocked by trees on the right. Your second must carry two intimidating high-lipped cross bunkers 60 yards from the green. Just to top it off, the green has three convoluted tiers and more than one edge where a poorly judged putt can run off into more trouble.


Leewood CC #15
464 yards // Par 4

You’ll need a good drive and an even better second shot to reach the green on this par 4, which played as a par 5 until the course was renovated a few years ago. Many mere mortals will hit a fairway wood into the green, and head pro Dean Johnson says setting up for one makes a big difference. “The ball should be just inside your front heel,” Johnson says. “The only time you play it further back in your stance is if you want a lower ball flight.” For solid contact, Johnson adds, “The swing should have a sweeping motion, not a downward strike like with an iron.”


Pound Ridge GC #2
Pound Ridge
451 yards // Par 4

A pond protects the green on the excruciatingly hard 2nd hole at Pound Ridge, so second-shot layups are the norm rather than the exception. You can still get your par, though, if you chip or pitch your approach shot with finesse. Head pro Brad Worthington says preparation for the shot is essential. He asks himself: Is the ball sitting up or down in the grass? “If it’s sitting down, I’ll play the ball back in my stance and account for more run.” Also, where do I want the ball to land, on an upslope or a downslope? When it comes to technique, he says, “I set up with 80 percent of my weight on my lead leg. For the backswing, I simply lift the club with my trail elbow, and for the downswing, I pivot toward the target and extend my arms. Since my arms are not over-accelerating relative to my body, each pitch comes out high and lands softly. A successful shot rolls slowly and finishes close to the pin.”


Golf Club of Purchase #16
435 yards // Par 4

Jack Nicklaus says he was inspired by the 11th hole at Augusta when he designed this hole. A lake protects the left side of the green, and, depending on your tee shot, you’re challenging it with an approach shot that may need to fly 200 yards. There is a bailout on the right side of the green, but it will leave you with a pitch back toward the lake. Director of golf Carl Alexander says, “The key to playing this hole is to keep your ball out of the penalty areas, right off the tee and left by the green. If you’re out of position on the tee ball, playing short of the green is always an excellent choice to save par and avoid making more than bogey. Par is well earned and often appreciated.”


Quaker Ridge GC #17
344 yards // Par 4

After two demanding par 4s to start the back nine, it seems like a relief to play a short one. But don’t count your par until the ball is in the cup. Hitting this tiny green is the challenge, according to head pro Mario Guerra, who cautions that a good sand game will come in handy if you miss. His formula for blasting up and out of the bunker with confidence? “Forget hitting two inches behind the ball. Take a steep backswing and aim to hit down and under the ball. Be sure to follow thru without trying to scoop the ball, and it will pop up onto the green.”


Salem GC #2
198 yards // Par 3

Head pro Kevin Breen points out that this fine par 3 plays downhill, but you should note where the pin is located, since the green is long enough to call for different clubs if it’s cut in the back or front. The green also has two tiers, and reaching the back one can be difficult if you don’t have the right club for the distance.

Hole 13 golf green
Century CC, Hole 13


Sunningdale GC #16
560 yards // Par 5

Head pro Christopher Toulson says every shot counts on this long par 5. “The ideal tee shot is down the right-hand side of the fairway, but Underhill Road and out-of-bounds lurk right. If you drive conservatively to the left, your next shot becomes more challenging, since it will be played into an area that is gradually narrowed by a creek on the right and a penalty area on the left. You can avoid this trouble by laying back, but then you will be faced with a third shot from a tricky downhill lie. Because the green is small and elevated and usually firm, having a shorter third shot from a level lie increases your chances of holding the green. But in order to access this level area, you’ll have to play a bold second shot with a longer club. The 16th green is spectacular. It cants gently from left to right with a subtle spine running through its center. If you mishit your approach shot, the green’s fierce false front will sweep your ball back, leaving you with an exacting uphill chip. The golfer will want a shorter approach into this demanding green, which in turn puts a premium on a well-played drive and second shot.”


Sleepy Hollow #18
426 yards // Par 4

Hole 15
Wykagyl CC, Hole 15

Few golf clubs generate more mishits by average players than mid or long irons, yet that’s just the club necessary to reach the elevated green on the finishing hole at Sleepy Hollow. Head pro David Young, who retired after 20 years at the club last year, says it’s not a hard shot to hit as long as you let the club do the work. “Take plenty of club and position the back of the ball in the midpoint of your stance,” he says, “then concentrate on a smooth, slow tempo. Don’t rush your swing, and don’t try to lift the ball; it will go farther and higher than you think.”

 Leewood hole 15 golf green
Leewood CC, Hole 15


Westchester Hills GC #7
White Plains
344 yards // Par 4

A driver may not be the best choice from the tee on this short-but-tricky par 4. The best club, in fact, is the one you never, ever hit to the right, since out-of-bounds hugs the right side of the fairway from tee to green, relieved only grudgingly by a bunker that can be almost as punishing. Hit a club that’s long enough to put you within short-iron range, though, because the approach shot to the small well-bunkered green needs to fly high and land softly.


Apawamis Club #16
186 yards // Par 3

An often overlooked but quite valid strategy for this uphill par 3 is to lay up in front of the green, then chip to leave yourself a makeable par putt. The shot is known as a “Patroni” at Apawamis, named for the former head pro who used it consistently to avoid the three deadly misses on the hole. Right or left leaves you at best with a bunker shot and at worst with a flop out of long rough, while any shot long and over the green is simply dead on arrival.

hole 17
Quaker Ridge GC, Hole 17

Of course, you can aim to hit the narrow, sloping green, but what are the odds?


Westchester CC West #3
460 yards // Par 5

Our finishing hole offers a multitude of challenges and opportunities. It’s a short par 5, but the scorecard doesn’t begin to tell the real story. “Off the tee,” director of golf Ben Hoffhine explains, “the fairway is generous but flanked by bunkers. About 230 yards from the green, the fairway pitches downhill, which can give your drive a big kick. Regardless of whether you get that advantage or not, you then have a decision to make. The green and approach are perched on top of a hill that’s covered in thick rough from 90 yards in. In other words, short is not good, so think twice before swinging for the fences. A layup to the 100-yard marker is safe, but it leaves a third shot severely up hill to a blind green. Once on the green, you have to navigate a ridge that plays havoc with many putts.” After you hole out, Hoffhine says, “Look back down the fairway and over to the fourth hole — one of many great vistas on the golf course.”

hole 18 golf green
Sleepy Hollow, Hole 18

Putt for Dough

The one club you need on every hole is your putter. We asked Bill Smittle, a PGA professional with special insights into the art and science of the flat stick, what he teaches his students about how to roll their rocks most effectively.

“Putting is all about geometry,” he says. “You have to read the line, get your ball started on that line, and control the ball’s speed.”

competitive golf hole

After coaching hundreds of good golfers over the years, Smittle concludes that most of us think we’re good at reading greens, but we’re not. Especially on Westchester’s slick carpets, most players under-read the breaks. He says we should follow these steps:

  1. Look for the general slope of the green in the surrounding landscape as you walk up to it.
  2. Find the best line from behind your ball.
  3. Step up and straddle the line to check your read with your feet.
  4. Go to the low side of the line to confirm.

“Then forget that nonsense about the three-foot circle. You want to make every single putt.”

skills tester scorecard

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.