18 of the Most Challenging Holes on Westchester Golf Courses

Anglebrook GC, Photo by John Fortunato

No sport in Westchester is contested on more visually stunning playing fields than golf. But beware: Beauty is often paired with a beast that devours birdies and pars.

Tremendously difficult choices had to be made to select the 18 holes that make up the Beauty and the Beast course. How can you leave out the iconic 16th hole at Sleepy Hollow? Or the 18th at GlenArbor? Or the 9th at Wykagyl? Or, or, or… All we can say is that we have an embarrassment of riches when it comes to first-rate golf holes in Westchester. These are only some of the ones where you’ll experience both the beauty and the beast of golf.


Anglebrook GC
No. 9 • Par 4 • 440 yards

Several unprintable words are often used to describe the immense cross-bunker in the center of the landing area on this difficult hole, and “beautiful” is seldom one of them. The controversial feature, though, reflects an element common on the best courses designed by architects from Donald Ross to Gil Hanse. The bunker may be more visually intimidating than appealing, but the award-winning clubhouse designed by Robert A.M. Stern lends a refined air to the scene.

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Anglebrook GC
Anglebrook GC, Photo by John Fortunato


Ardsley CC
No. 15 • Par 4 • 326 yards

The visual appeal of this short par 4 is readily apparent from the tee. The wide fairway stretches below you to a pond sparkling in front of the well-bunkered green. Its beast appears, though, when the player must choose how close to challenge the hazard from the tee and again when deciding whether to go pin-seeking on the approach or to play it safe to the center of the green.


Brae Burn CC
No. 15 • Par 5 • 505 yards

Short and lovely, this oft-photographed par 5 not only features a risk-reward second shot (or layup) to a water-guarded green but also a chance to inspect the stone trestle along the right side of the fairway, built in the early 20th century for a railroad that never ran. Seasonal flower beds lend spectacular color to the vista.


Hudson National GC
No. 16, Par 3, 224 yards

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What makes this arguably the most scenic hole in Westchester? The rolling green floating in a sea of fescue? The classic stone walls framing the picture? Or is it perhaps the expanse of the Hudson River stretching across the horizon? Regardless, once you’ve taken it all in, hitch up your pants and make a mighty swing. You’ll need it to reach the green located at the very edge of your golfing ability.


Whippoorwill Club
No. 18 • Par 4 • 437 yards

The beast comes out on the tee shot on this harder-than-it-looks par 4. A drive to the left, even if it’s in the fairway, may not leave a manageable approach angle to the uphill green. Yet, a fairway bunker on the right menaces the slicer. From the center of the fairway, it’s worth a moment to enjoy not just your triumph but the view of the modern classic clubhouse and the flags flying behind the green.


Westchester CC
South No. 9 • Par 4 • 398 yards

Beasts seen and unseen threaten the golfer who can’t find the fairway from the tee on this hole. Unseen is the water left of the landing area, which comes into play on a long, erratic draw. Seen to the right, though, is a visually stunning red barn that reflects the history of the property as a farm before it was purchased by John Bowman in 1919. Yes, the barn comes into play on the second shot from the rough for slicers off the tee.

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Westchester CC, Hole 9
Westchester CC, Hole 9. Photo by Leif Skodnick, courtesy of WCC


Bedford G&T
No. 14 • Par 4 • 426 yards

There’s not much to see from the tee box on the 14th hole at Bedford Golf & Tennis, but once you’ve hit your blind drive up and over the hill, a perfectly bunkered multi-tiered green comes into view. It’s best to enjoy the beauty before attempting the long, uphill beast of a second shot.


Summit Club
No. 17 • Par 3 • 185 yards

“Hang Time,” as this lovely hole is named on the scorecard, aptly describes the experience of hitting from its elevated tee to a generous green surrounded by sand and water. The par 3 is one of the major improvements to the Rees Jones-renovated Summit Club course, which opened last year.


Winged Foot GC
West No. 9 • Par 5 • 513 yards

Nine West offers perhaps the best view on the entire property of the iconic Winged Foot clubhouse. It’s a heck of a golf hole, too. Tillinghast described it as one of the toughest holes on the course, and Gil Hanse’s restoration of what he called a “wedge green” brought new perimeter pin positions into play.


Scarsdale GC
No. 14 • Par 4 • 455 yards

The only beauty you want to see from your drive here is your ball bouncing down the center of the fairway. When you get to the ball for your second shot, though, take a moment to enjoy the view of what seems like half of Westchester County from the hilltop. Then, follow head pro Anthony Casalino’s advice, by hitting a hybrid that lands in front and rolls onto the small, tricky green.

Scarsdale GC, Hole 14
Scarsdale GC, Hole 14. Photo by John Fortunato


Old Oaks CC
No. 7 • Par 3 • 175 yards

What a charming beast of a hole! It is indeed beautiful, with a winding brook beside the green, classic flash-faced bunkers pinching it, and the stunning halfway house in the background, but the slightest miscue from the tee can easily send your ball to a sandy or watery grave.


Salem GC
North Salem
No. 17 • Par 4 • 372 yards

Our golf panel had some spirited discussions on this hole, all over the best way to play it. The green, perfectly framed by pine trees but blind on the second shot, is canted to the uphill fairway, so how you play your approach depends on where you placed your drive.


Trump National GC
Briarcliff Manor
No. 2 • Par 5 • 515 yards

A par-5 hole doesn’t have to be long to be challenging. The 2nd hole at Trump National combines beautiful hazards, including a stream that meanders in, across, and along the fairway to a pond that guards the green with fairway bunkers that punish the player who tries to keep dry by hugging the left.


Metropolis CC
White Plains
No. 6 • Par 4 • 416 yards

What could be more beautiful than a hole that looks like it would be right at home on Augusta National? The 6th hole at Metropolis fits that description and adds a few bestial features, as well. There’s the fairway bunker right that is the slicer’s worst nightmare off the tee, then the innocent-looking bunker in the front-center of the green that seems to be in play for everyone no matter where the cup is cut.


Knollwood CC
No. 18 • Par 4 • 473 yards

The finishing hole at Knollwood is known as a beautiful round-wrecker. The view from the tee box takes in the expansive fairway, the hazard that defines the hole along the right side, and the elevated green, far, far in the distance. There’s no easy way to play this beast. It requires a long, well-placed drive and a long, well-aimed approach shot to reach the green with a chance for par.

Knollwood CC, Hole 18. challenging holes
Knollwood CC, Hole 18. Photo by John Fortunato


Saint Andrew’s GC
No. 4 • Par 4 • 401 yards

Few shots in golf are as soul-satisfying as a drive from an elevated tee that falls from the sky to a valley fairway far below. The 4th hole at the Saint Andrew’s GC provides that wonderful experience, as well as tremendous views of at least a half-dozen holes on the course from the tee. Beware the beast, though. He lurks behind the sharply elevated and even more sharply contoured green.

Saint Andrew's GC, Hole 10. challenging holes
Saint Andrew’s GC, Hole 10. Photo by John Fortunato


Mount Kisco CC
Mount Kisco
No. 10 • Par 3 • 201 yards

Take a moment to enjoy the view of the stone bridge and framing trees on this picture-perfect par 3 before you challenge the unruffled sand and flowing water that protect its small, subtly contoured green. Then, choose a club that hits straight and true, because the beast here eats balls that fly offline.

Mount Kisco CC, Hole 10. challenging holes
Mount Kisco CC, Hole 10. Photo by John Fortunato


Hollow Brook GC
Cortlandt Manor
No. 8 • Par 5 • 531 yards

We finish with a flourish on a hole that’s not only beautiful but also a strategic masterpiece. From the tee, take in the view of the surrounding holes and the clubhouse on the hill before you try to drive the ball past the bunkers guarding the right side. Then make your strategic decision to play your next shot over or around or next to a stately sycamore tree impinging from the left edge of the fairway.

challenging holes

Related: 8 Great Courses Everyone Can Play

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