18 Golf Holes in Westchester With Big Risks and Rewards

Golf is all about decisions. Do you go for broke or play it safe? Chance a birdie or guarantee a par? We chose 18 of the best holes in Westchester where you must choose: Is the risk worth the reward?

Hole 1

Sleepy Hollow CC

#1 // 418 yards // par 4

Head Pro A.J. Sikula says the opener at Sleepy Hollow is “underrated as a risk and reward hole. Drives to the right of the fairway are safer off the tee because of the big fairway bunker on the left, but they leave a very tough angle into the green, particularly when the hole location is right front. The reward for challenging the left side off the tee is a slightly longer but better second shot.”

Sleepy Hollow GC Hole 1
Sleepy Hollow GC Hole 1

Hole 2

Anglebrook GC

#15 // 290 yards // par 4

Are you straight and decently long off the tee? If so, you’ve got a good chance to thread the needle and drive this inviting green to set up an eagle putt. But long and left is out of bounds or, at best, in a greenside bunker, while long and right is probably going to catch the wrong side of the mogul next to the green and disappear into the rough. The safe play is a 200-yard layup to the cross bunker off the tee, then a wedge snuggled up to the pin for your birdie.

Hole 3

Trump National GC Westchester

#5 // 490 yards // par 5

A well-struck tee shot that avoids the water on the left and out of bounds right puts you in position to go for the green in two — if you dare. Beware of the creek to the right of the green, however, as well as the tall tree that stands in the front.

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Hole 4

Ardsley CC

#15 // 326 yards // par 4

One of the best design improvements at Ardsley last year was the reconfiguration of this classic short par four. The green was doubled in size so that now the carpet wraps around the full width behind the pond that keeps big hitters (usually) from driving the green. The new configuration created a daunting new pin position for those who have pinpoint control of their wedges.

Hole 5

Brae Burn CC

#8 // 190 yards // par 3

There are four ways to miss this beautiful par three. Short is wet, long is dead, left and right are both bunkered. The reward of a well-struck shot, of course, is a birdie putt (as long as you’re below the hole). The safe play — almost a sure par — is to lay up short of the pond to eliminate the four misses, pitch it close, and take your three to the next hole.

Hole 6

Metropolis CC

#6 // 416 yards // par 4

One of the county’s most well-designed holes, this par four richly rewards the player who can draw the ball off the tee, hit the speed slot, and leave a short iron into a devastatingly demanding green. The risk lies in overcooking the draw, which leaves little option other than a safety shot of some sort. The safe play to the center of the fairway can keep the big number off your scorecard.

Hole 7

Westchester CC West

#18 // 475 yards // par 5

The final hole on the championship course at Westchester CC looks so short, but it plays so long. It’s uphill all the way, so only the longest hitters have a chance to reach in two. There’s risk and reward for those laying up as well, though. The key decision is the second shot, which might normally call for a fairway wood to get as far up the hill as possible. That brings wicked fairway bunkers into play, and few of us want to try a 150-yard blast over a bunker rim that’s above our head.

Hole 8

Winged Foot GC West

#3 // 192 yards // par 3

Lay up to a par three? Unthinkable, perhaps, unless you’re looking at a tiny, heavily contoured green flanked by frightening bunkers. It’s an even more reasonable decision when you see the inviting landing area in front of the green that leaves a sweet chipping path to almost any pin position for a one-putt par. That’s the play Billy Casper chose when he won the 1959 US Open at Winged Foot.

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Brae Burn CC, Hole 8
Brae Burn CC, Hole 8

Hole 9

Mount Kisco CC

#16 // 466 yards // par 4

Risks are many and rewards for taking them are few here. A long drive with a perfect draw can bring you closer to the green but force you to hit your approach off a downhill lie. A shorter drive rewards with a level stance but brings a creek crossing the fairway into play for the second shot. Pick your poison!

Hole 10

Old Oaks CC

#11 // 306 yards // par 4

The elevated green may not be quite drive-able, but it’s sure tempting to blast one off the tee and hope it lands on the short grass in front. Your drive is more likely to end up in one of the numerous bunkers, though, or maybe even tangled in the tree guarding the left approach. Two hundred yards straight off the tee takes all that risk out of play and rewards you with an easy full wedge into the green.

Hollow Brook GC, Hole 10
Hollow Brook GC, Hole 10

Hole 11

Whippoorwill Club

#7 // 425 yards // par 4

Architect Charles Banks reputedly lost a steam shovel in the pond when he built this hole, which is a good indication of how tough it is. The standard play is straight off the tee over the pond to the elbow of the dogleg, which leaves a long uphill approach. If you can manage a high draw, however, you can cut the corner and substantially reduce the length of your second shot. That draw must be high, though, because the corner is fortified with tall trees.

Salem GC, Hole 11
Salem GC, Hole 11

Hole 12

Bedford Golf & Tennis

#17 // 321 yards // par 4

A deft driver of the golf ball can thread their tee shot between the out-of-bound stakes left and the fairway bunker right to reach the throat of this short par four. The risk-free route entails a 200-yard safety shot from the tee box to set up a wedge-in approach.

Hole 13

Rye GC

#8 // 333 yards // par 4

This delightful little hole is the only one in Westchester that brings Long Island Sound into play. The water snuggles along the entire left side of the fairway, waiting to drown an errant tee shot. There’s a water hazard on the right side, too, so only the brave shaper of the ball will dare risking driver off the tee.

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Hole 14

Saint Andrew’s GC

#12 // 532 yards // par 5

A solid drive down the left side gives you a chance to reach this green in two. In fact, even a second shot aimed at the right side of the green can roll on even if it’s a bit short. Too far right, though, and red stakes come in to play and short left is protected by bunkers. A conservative second shot to the center of the fairway takes all the trouble out of play and sets up a par.

Hole 15

Hollow Brook GC

#10 // 331 yards // par 4

Yes, the hole plays steeply downhill, but can you reach the green from the tee? Only the brave will try since water and sand will punish even the slightest miss to the right, and the elevated green will reject those that land front left. A safe drive to the fairway in front of the bunkers leaves a short iron to the multi-level green.

A man on a green in Ardsley
Ardsley CC Hole 15

Hole 16

Siwanoy CC

#14 // 388 yards // par 4

This hole would be a routine par were it not for the creek crossing the fairway exactly in the landing area for most tee shots. The drive is downhill, however, so it’s entirely possible to carry the creek if you are straight and long off the tee. Just beware of the trees crowding the right side of the fairway.

Hole 17

Summit Club

#17 // 170 yards // par 3

The degree of risk on the Summit Club’s penultimate hole depends entirely on the pin position since any cup near the edges of the putting surface can spell bogey. The green is raised and sharply contoured as well, so it repels even the slightest miss. Unless you have pinpoint accuracy, the safest shot is to the center.

Hole 18

Salem GC

#11 // 370 yards // par 4

A crucial decision must be made on the tee box of the eleventh hole at Salem GC. You can choose driver, which brings the bunkers that bracket the fairway into play (not to mention out-of-bounds left and water right for the truly errant drive) but sets up a nice wedge to the blind green. Or you can decide to lay back with a shorter club from the tee, eliminate all the trouble, and give yourself a simple mid-iron to the green.

Risk and Reward Scorecard
Risk and Reward Scorecard

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