R5 Best 18 Places to Play Golf in 2012 in Westchester and the Hudson Valley, Upstate NY

Driveable par fours. Par fives so long that even the pros lay up. One-shotters you can barely reach with a driver. Extreme golf holes are the ones you remember, the ones you laugh (and cry) about over beers at the 19th hole. How is any mere mortal supposed to make par on a hole so long your second shot requires a howitzer? Whose bright idea was it to put the hole within half-wedge distance downhill over water? When you par a 600-yarder, you crow about it for days. When your scorecard shows a double bogey on a hole even your grandmother could par, you hang your head in shame.

We chose 18 of the longest and shortest holes in Westchester, just to see what kind of golf course they would make. On the surface, our course looks pretty standard at 6,764 yards and par 72 from the blue tees. But we ended up with a monster front nine that stretches for almost 4,000 yards. The back nine is probably harder, even though it’s well under 3,000. Both are guaranteed to challenge every facet of your game.

One thing we proved, by the way, is that long doesn’t necessarily mean better. You can have just as much fun — and heartache — trying to make par by teeing off with a five iron and approaching with a delicate wedge as you can pounding driver, three wood, nine iron. In fact, the mental challenge of short holes adds a whole different type of excitement to the game. Golf, after all, isn’t about who can swing the hardest, it’s about who can get the ball in the hole in the least number of strokes. That’s the long and short of it.

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» See how we put together this dream course
» See to our 18 favorite holes
» Honorable mentions — our other favorite long and short holes



How We Do It:

Someone says it every year because it’s true: It’s a tough job but somebody has to do it. Our panel of players and I visit as many courses as we can manage during the course of the golf season. This year, thanks to the generous hospitality of the members and staff of Westchester’s private clubs, we played 35 rounds in quest of the best long and short holes in the county. We also talked to the club pros and many members about the holes and the way they play them. Finally, after much back and forth and give and take, we select 18 holes to feature. It’s entirely subjective, but we take it seriously.

Our panel of players included Dan Berger, Rye Brook; Ned Branthover, Bronxville; Craig Burrows, Yonkers; Casey Egan, White Plains; Tim Finneran, Crestwood; Alan Kalter, Stamford; Mark Maznio, Somers; Joe Miressi, New Rochelle; Ken Nilsen, Mount Kisco; Thomas Ralph, Pelham; Bruce Schoenberg, Hastings; Robert Westenberg, Bedford; Ralph Wimbish, Mount Vernon; and John Zanzarella, Ossining. Westchester and Hudson Valley Magazine Publisher Ralph A. Martinelli joined us on many rounds and held his own, despite playing with a brand-new driver that was balky at times.


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hollow brook golf club

1. Hollow Brook Golf Club, Cortlandt Manor

Hole 13 • 588 yards • Par 5

Just to make sure you know this is the long side of our imaginary golf course, we chose one of the longest, toughest par fives in Westchester for the opener. It’s the 13th at Hollow Brook, a full three-shot hole if there ever was one. Your drive has to be both long and straight — at least 260 yards — just to reach the dogleg, which is protected by massive bunkers and out of bounds all along the right side.

In many ways, your second shot is the key to par. Since you are still 300 yards from the hole, you’ll want to plan ahead for the best distance and angle for your third shot. Don’t get greedy. The fairway narrows to less than 20 yards as you get closer to the green, squeezed by a bunker the size of Montana that runs along the left side. Check the pin position before you choose a club for your third shot, too. The green is humpbacked and a full 35 yards deep.



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2. Metropolis Country Club, White Plains

Hole 10 • 453 yards • Par 4

Many holes at Metropolis are protected by trees, but few as solidly as the 10th. The hole is a downhill dogleg right that appears to set up for a fade off the tee. It better be a long, long fade, however, since anything right and shorter than 250 yards off the tee will end up without even a view of the green, much less a shot at it. Anything much shorter — even if it’s in the middle of the fairway — probably won’t offer a clear shot around the trees guarding the dogleg.

Whether it’s your second or third shot into the green, play it to the right side and consider bouncing it on. The green slopes from front to back so it’s easy to end up in the rough beyond.




3. Sunningdale Country Club, Scarsdale

Hole 3  • 215 yards • Par 3

From the tee you see a wide, inviting green waiting for you across a picturesque dale where a line of apple trees leads down to a pond. But don’t be fooled by the benign setting — the third hole at Sunningdale will eat you alive if your tee shot is the slightest bit under-clubbed or under-hit.

This difficult par three plays even longer than it measures. The green lies higher than the tee, something you may not realize until you get on the green and look back. If your tee shot falls short of the green in the fairway, it will roll 40 yards in the wrong direction down the steep, closely-trimmed apron. Long is no prize, either, since you’ll be chipping out of deep rough onto a green that slopes steeply away from you. Depending on the pin position, the right front bunker isn’t the worst place to land if you miss the green.

Once you have the flat stick in your hand, you have to deal with a swale running through the middle of the green that divides the putting surface into two treacherous tiers.




4. Mount Kisco Country Club, Mount Kisco

Hole 5 • 453 yards • Par 4

You don’t normally expect an impossible green on a long par four, but that’s what sits at the top of the hill on Mount Kisco’s fifth hole. The green doesn’t just slope from the back left to front right — it falls away like the deck of the Titanic just before it slipped beneath the waves. In other words, don’t try to putt from above the hole.

First you have to get there, of course, and that’s a long, uphill battle — literally. The fairway slopes from left to right, so slicers and faders are at a distinct disadvantage. Even a good drive to the left center will leave you with an uphill, side-hill lie for your second shot, which will probably be with a fairway wood since the USGA prohibits the use of rocket launchers. Many members play this conservatively as a par five. Considering the many ways a four can turn into a seven on this hole, that’s not a bad idea.




5. Hudson National Golf Club, Croton-on-Hudson

Hole 12 • 479 yards • Par 4

This is a tour-length, tour-tough par four. Your first clue about the hole’s difficulty should be that it plays as a par five from the white tees, which are just a few yards back. Truly long hitters — Bubba long — have the option of cutting the left dogleg from the tee, but a miss can be disastrous if it finds the hazard left or the bunkers right of the fairway. A more conservative play is to the center of the fairway right of the bunkers, which leaves a lengthy but manageable approach shot.

One caution: Avoid the bunkers short and left of the green at all costs. The green is slightly elevated and falls sharply toward the fairway on the right side. Like all the greens at Hudson National, it’s also huge, so double-check the distance to the hole location before you swing away.



fenway golf club

6. Fenway Golf Club, Scarsdale

Hole 6 • 227 yards • Par 3

You wouldn’t think you’d need five bunkers to guard an uphill par three that’s 227 yards long, but that’s how many you encounter on the 6th hole at Fenway. And they come into play more often than you think, too, since most players are using a wood — drivers aren’t unheard of — to try to reach this green.

As if length from the tee weren’t enough, the green has several difficult pin positions, too. One of the hardest is in the center where a large hump means that nothing longer than a 12-inch putt can be taken for granted.



westchester country club west

7. Westchester Country Club West, Rye

Hole 14 • 573 yards • Par 5

Can you make this green in two? It’s possible, but not probable. The hole plays downhill, so you will get a little extra from your drive if you put it in exactly the right place. The green is long with three tiers, however, so it’s not likely that anything but two big, big hits will get you there.

On the tee, take aim at the fairway bunker you see in the distance. That’s a little over 300 yards from where you’re standing, so you don’t really have to worry about landing in it unless your name is Fred Couples. The most important thing to do off the tee is to hit a long, solid draw. You can cut the corner left, but if you over-pull just a little, the trees will get you.

Smart players decide how far they want to hit their third shot before they hit their second. The green has a false front you don’t really see from the fairway, so make sure your approach carries all the way.




8. Pelham Country Club, Pelham Manor

Hole 13 • 454 yards • Par 4

You usually want to bomb it off the tee on a big par four, but a long, long drive can be too much of a good thing on the 13th hole at Pelham. Your aiming point is a big oak tree straight away, but hit anything over 245 yards and your ball will run through the fairway of the sharp dogleg left. A long high draw around the corner, of course, is the golden shot. If you can pull it off, you’ll have a midiron to the green.

Hitting the green is a whole other matter. At about 4,000 square feet, it’s not exactly tiny, but it looks really small from 200 — or more — yards away. Bunkers protect it right and left, and subtle, hard-to-read breaks make birdie putts difficult to pull off.




9. Waccabuc Country Club, Waccabuc

Hole 13 • 438 yards • Par 4

Head pro John McPhee plays this long, straight hole with a driver and a hybrid, but then he also holds the course record of 62 and obviously knows what he’s doing. In truth, as long as you can hit it straight, there’s no reason not to score well here. A line of trees presents the biggest problem to those who stray off the fairway left; there are more to the right, although there’s a little more room on that side. You’re going to have a long approach shot no matter where you are, though, so it’s essential you make it from the short grass.

The green is deep — over 30 yards — so club selection for the second shot is not automatic. Running the ball onto the green isn’t unusual since it is level in the front. The back half slopes sharply back to front, though, so read your putts carefully if the pin is anywhere behind the mid-point.



bonnie briar country club

10. Bonnie Briar Country Club, Larchmont

Hole 7 • 309 yards • Par 4

Just as we began the front nine with the longest hole on our imaginary course, we start the back with one of the shortest, a surprisingly difficult par four. What makes it hard? Certainly not length, since it’s only 309 yards, practically a chip shot for some tour pros. But for them, as for us, it’s a shot that better be right.

This may be the shortest par four on our course, but don’t try to drive the green. It’s elevated — a lot — and surrounded by thick rough and some nasty bunkers. Watch where you play your conservative iron or hybrid off the tee, too. The landing area slopes right to left and feeds into a fairway bunker just where you don’t want it to — about 100 yards short of the green. Laying up to perfect wedge distance may not be as easy as it sounds.

Perhaps the most unnerving shot on the hole, though, is the one to the green. You can’t see the surface from the fairway below. In fact, you may not even see the flag. Unless you have a deep store of local knowledge, take a minute to walk up to the green and find your target. It may add a few minutes to the round, but the jaunt will probably save you a stroke or maybe even two.




11. Elmwood Country Club, White Plains

Hole 17 • 340 yards • Par 4

The 17th hole at Elmwood might not be a driveable par four, but it’s fun to try as long as you’re not afraid of a little sand and have a forecaddie to find your tee shot just in case. Your drive is blind, but if you stay to the left center, hit a solid 250, and have a lot of luck in your bag that day, the ball will catch a downhill chute that leads toward the green. If you really tag one, you’ll end up in a bunker that spreads completely across the front of the green and where an up-and-down par is entirely possible.

If you’re not lucky, you’ll have a steep downhill lie for your approach — maybe out of the rough — not something you want since your second shot then has to carry that bunker and stop immediately on the tiny green. The safer play is to take a 200-yard club off the tee to a flat area in the fairway, which will then leave you with an easy short iron or precise wedge to the pin.



leewood golf club

12. Leewood Golf Club, Eastchester

Hole 11  • 120 yards • Par 3

Legend has it that when Babe Ruth was a member at Leewood, he would bet his playing partners that they couldn’t throw a ball from the tee on the 11th hole to the tiny green some 60 yards below. The perfectly round green looks so close, how could you miss? It was a sucker bet, of course, because even the Babe could just barely hurl a golf ball that far. It’s not much easier getting the ball safely on the green with a wedge of some sort, either.

The green is guarded by three bunkers, not to mention a lovely but wicked pond in front. Distance control is everything, since too short is obviously wet while too long leaves you with a bunker shot that could end up in the water as well if you hit it a little thin. The best strategy: Pick your club carefully and think positive thoughts.




13. Willow Ridge Country Club, Harrison

Hole 18 • 475 yards • Par 5

This should be an easily reachable par five, a simple birdie that puts a smile on your face at the end of your round at Willow Ridge. But don’t count your birdies until they’re hatched. This may be a short hole, but it’s not a pushover.

The terrain is what kills you. To start, there doesn’t seem to be a landing area for your tee shot among all the mounds and moguls in the narrow fairway. You’ll also find your drive doesn’t travel as far as you expect since you’re hitting it uphill. The second shot is even tougher. You’ll be hitting off an uneven lie to a blind target and again uphill — even more steeply this time. Go ahead, hit all you’ve got and then some. While you’re at it, aim for the left side of the fairway, which will give you the best angle into the green for the third shot you’ll almost certainly have.

The green is flanked by six bunkers on the sides plus one in the back. It has two tiers and a slick false front, so plan your third shot with care.



trump national golf club

14. Trump National Golf Club, Briarcliff Manor

Hole 4 • 353 yards • Par 4

This is the shortest par four on Trump National, but it is far from the easiest. Par or better is entirely possible, but it takes a disciplined, accurate player to do it.

A driver off the tee is folly. Any shot slightly left will end up in the pond that lines that entire side of the fairway, while even a mild banana ball will end up in the woods — or worse, out of bounds — on the right. Even a long, straight drive will probably go through the fairway and leave no shot to the green.

The smart play is a hybrid or fairway wood off the tee, followed by a pinpoint second shot to the deep but narrow green nestled between rough-covered mounds and three very punishing bunkers.



ardsley country club

15. Ardsley Country Club, Ardsley

Hole 15 • 326 yards • Par 4

What golfer doesn’t love to hit a soaring drive on a downhill hole? That shot might be fun, but it will wreck your score on this short but demanding par four with a ball-devouring pond at the bottom of the hill.

The 15th hole at Ardsley is a thinking golfer’s hole. In some ways, with a semi-blind tee shot and water between you and the green, it’s an echo of the first hole on the course — only better. You have a few more options off the tee, although the best play is to the flat area in the fairway about 210 yards out. Pick the distance you want for your second shot and choose your club from the tee accordingly.

The green presents challenges of its own. It’s good sized, about 5,000 square feet. Its relentless contours give long putts more breaks than a Jim Bouton knuckleball and make you look twice at every three-footer.




16. Westchester Hills Golf Club, White Plains

Hole 7 • 344 yards • Par 4

The seventh at Westchester Hills is a nasty little hole fully capable of bringing tears to the eyes of grown men — especially those who think they have the game to overpower it. Like most short par fours, the best way to play this hole is with your brain, not your brawn.

You are welcome to pound a driver off the tee as long as you can hit it laser straight. That picturesque wooden fence you see running the length of the hole on the right is out of bounds. Notice how close it is to the fairway? Maybe it’s a sign you should be using a scalpel instead of a chainsaw to dissect this hole.

Even if you play it safe, however, there’s no assurance that your second shot will nestle up close to the pin. The green is the size of a ping-pong table and just about as hard to hold with anything other than a perfect floating wedge. Complicating matters are three bunkers, one of which—the deepest, naturally—is inconveniently located right in front of the green.



brae burn country club

17. Brae Burn Country Club, Purchase

Hole 5 • 140 yards • Par 3

The fifth hole at Brae Burn may be a perfect par three. It has a forced carry over water, plenty of sand, a large undulating green, and scenic features like a trickling waterfall and colorful shrubs and flowers that are good for the soul.

Depending on the placement of the tee markers and the pin position on any given day, the hole can play from 120 to 160 yards, so proper club selection is crucial. The three bunkers protecting the green can cause problems, but the real danger is landing your ball above the hole, especially if there is a front pin. You probably won’t putt into the water if you stroke it a little strong, but your ball can very easily trickle down the false front and make you pray a little as it heads toward the pond.



brynwood golf and country club

18. Brynwood Golf & Country Club, Armonk

Hole 18 • 477 yards • Par 5

It is possible to reach the green in two on the 18th hole at Brynwood, but it takes a couple of mighty blows to do it. The hole plays not only uphill but side-hill most of the way, and the design of the green complex discourages a go-for-it second shot. It may be hard to believe that a 477-yard par five is a three-shot hole, but this one is.

Even then, it’s not exactly an automatic par. The fairway is invitingly wide — except where you want to land your ball. It also tilts to the left, so drives that land in the center may well end their run in the rough. From the tee, you can aim at the bunker on the right side of the fairway, but be aware that it’s about 250 yards away, so a good drive will find it. The bunker also serves another purpose — it makes the fairway only about 15 yards wide at that point.

There’s another bunker awaiting your second shot. This one’s on the left side of the fairway about 100 yards from the green — exactly where you’d want to lay up. You can go ahead and bomb over it, just remember that you’re still hitting uphill, so you’ll need another club to clear the bunker. Three traps guard the green, two on the left and one on the right, but the toughest obstacle to par is the tree on the left front.



Other Long and Short Holes of Note:

Knollwood #14
287 yards, par 4
A stand of tall trees and some marshy ground off the fairway keeps players from driving this tiny green.

Scarsdale #13
290 yards, par 4
With a blind tee shot, this can be a nerve-wracking short hole. It’s best played with something less than a driver since the green is tucked into a corner far to the right of the tee box.

Glen Arbor #7
206 yards, par 3
Even though it’s downhill, your shot must be all carry to this difficult tiered green.

Old Oaks #11
310 yards, par 4
Yes, you can drive this green, but the odds are against you. The green is elevated and you’ll have to carry a huge tree that blocks a straight shot from the tee.

Anglebrook #4
582 yards, par 5
Hit as far as you want on the first shot — you’ll still be laying up to the water around the corner and in front of the green on your second.

Pound Ridge #5
309 yards, par 4
Pete Dye probably knows, but it’s hard to say how many bunkers lie between the tee and the green on this short tester. They’re not only in the rough, either, but dot the fairway just about everywhere you’d want to hit.

Salem #14
565 yards, par 5
Placing your second shot in the right place to leave a solid short iron to the green is the key to par on this hole, where the third shot plays over water.

Wykagyl #4
144 yards, par 3
Two tiers on this narrow green make precision off the tee essential. Short is disastrous and long isn’t much better.

Whippoorwill #5
455 yards, par 4
This is the number one handicap hole for a reason. It takes two shots both long and well-shaped to reach the green in regulation, then an eagle eye and steady nerves to putt the ball into the hole.


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