Fantasy Fairways

Westchester’s best 18 holes test your golf savvy, skills, and strategy.


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Ask three golfers what makes the best golf hole, and you’ll get at least six answers. One wants a difficult challenge that’s fair. Another a scenic view with birdie potential. The third is going to say the best golf hole rewards well-executed shots while punishing bad ones, plus offers some visual razzle-dazzle without being too tricked up with gimmicks and gimcracks. In other words, “best,” like beauty, is in the eye of the beholder.

In an effort to find out what our golfers’ eyes like to see, we asked the head pros and players of Westchester’s courses to identify their favorite golf holes this year without giving them any specific criteria. Then we took our panel of players to the courses to check out their choices for ourselves. The result is this composite course of the best golf holes in Westchester, a track that’s 7,219 yards long and plays to par 71.

It’s a fantasy course made up of 18 distinctive holes, each of which offers its own version of “best.” Some are tough and long, others are short and tricky, many are visually stunning, mentally exhilarating, and physically challenging. They all meet our definition of “best” as defined in the box on page 30A.


Trump National Golf ClubExecutive VP Dan Scavino putts out at Trump National #10

Trump National Golf Club #10

375 Yards, Par 4
Briarcliff Manor

The fantasy fairways course starts with what looks like an easy, short par 4, and that’s exactly what it is — as long as you don’t get greedy. The hole plays downhill, so you don’t need anything more than a hybrid or even a mid-iron to your preferred wedge distance. Go for more and you’ll end up in one of the new waterfalls that grace the valley in front of the green. That’s where your ball will go, too, if your approach shot is a yard or two short of the putting surface. What really protects par on this hole, though, are the multiple contours on the green, not to mention the strong break toward the valley that affects every putt.


Anglebrook Golf Club #9

384 Yards, Par 4

You might put your driver away on this hole, but don’t relax, because the ninth hole at Anglebrook simply cannot be taken for granted. It’s a prime example of designer Robert Trent Jones, Sr.’s talent for testing direction and distance control while rewarding two perfectly-struck shots, a theme on most of the holes on one of Westchester’s best but most-often-overlooked courses. Even the straightest of long hitters will need to dial back from the tee because anything hit over 250 yards will disappear into the 50-yard-wide abyss at the end of the fairway. It’s a good idea to bite off 240 yards if you can, though, because you’ll want to hit as lofted a club as possible into the severe green on the other side of the environmentally protected waste area. Distance control matters going into the green, too, since putting from above the hole is much like trying to guide a steel ball bearing down on the roof of the Chrysler Building into a coffee cup on the sidewalk below.


Winged Foot Golf Club

Winged Foot Golf Club East #6

194 Yards, Par 3

There are some who argue — quite justifiably — that A.W. Tillinghast’s true genius is displayed in his one-shot holes. This gem on the East Course at Winged Foot is an example of the man’s work at its best. The mid-length hole plays uphill to a small green nestled against a colorfully landscaped hillside, the putting surface unseen from the tee box. It’s one of the smallest greens on either the East or the West Course and, while you may not be able to spot the cup from the tee, you have a great view of all four very, very serious bunkers — two left, one right, and a huge one behind. You’ll want to take your time lining up your putt; the green may be small, but it is full of not-so-subtle breaks exaggerated by the slope of the hillside.




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