The 18 Most Fun Holes in Westchester

Yes, golf is hard. But it can be fun, too, if you stop taking yourself quite so seriously and relish the challenges the course presents. This collection of 18 holes (par 72, 6,869 yards) will entertain as well as test your skills… all part of the fun!


Hole 6 • Willow Ridge CC

Photo By John Fortunato

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John Reeves approaches the 6th hole at Willow Ridge Country Club​ 

Par 4 • 400 yards
Just the right amount of risk spices up the picture-perfect 6th hole at Willow Ridge. The downhill tee shot sets the tone for fun, while the no-mercy carry over water to the expansive green quickens your pulse.


Hole 16 • Anglebrook GC

Courtesy of Anglebrook Golf Course 

Anglebrook Hole 16

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Par 5 484 yards
Head pro Rob Davis says he enjoys this risk-reward par 5 because “it makes you think twice on every shot.” A big drive puts you in position to reach the green in two, but a too-big tee shot brings gnarly rough at the end of the fairway into play. The green is gettable with a good second shot, but most of the putting surface runs away from you, so you need a perfect high floater to set up an eagle putt.


Hole 18 • Bonnie Briar CC 

Par 4 304 yards
Few holes are more fun than a short par 4 with options. The safest tee shot on Bonnie Briar’s finishing hole is a 200-yarder that leaves a seemingly easy wedge to the two-tiered green. But the small elevated green can be tricky, so think before you hit.


Hole 8 • Brae Burn CC

Par 3 190 yards
Brae Burn’s longest par 3 often intimidates the strongest players, but that doesn’t take the fun out of the hole. Straight and long carries the pond, but there’s actually a layup-and-pitch option that careful players use more often than you’d think.

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Hole 16 • Glen Arbor GC 

Par 4 337 yards
Two shots over water can be fun, especially if they’re part of a short, pretty par 4. As you might expect, this short hole places a premium on hitting the fairway. Depending on how aggressive you were off the tee, you’ll have a mid- or short iron to a wide but shallow green.


Hole 12 • Hollow Brook GC 

Par 3 162 yards
With water, framing bunkers, and a ridge that divides the green into three sections, “you can attack it or play safe,” according to director of golf Phil Eyre. He adds, “When the foliage turns in the fall, I can sit there and contemplate it all day.”


Hole 5 • Hudson National GC

Par 4 412 yards
Hudson National golfers now have another great hole to play with the opening of a new tee box on the 5th hole that turned it into a true dogleg right. General manager Theron Harvey says, “You need to hit a driver off of the tee instead of floating an iron down the hill like in the past. It is a special golf hole now!”


Hole 5 • Mount Kisco CC

Par 4 453 yards
The “new” 5th hole at Mount Kisco isn’t necessarily any easier (how do you make a 453-yard uphill par 4 “easy”!?), but its green is a lot more reasonable following the recent recontouring of its punitive false front and back tier.


Hole 18 • Old Oaks CC

Photo By John Fortunato

Nick Maselli pitches to the 18th green at Old Oaks Country Club. ​ 

Par 5 547 yards
What’s more fun than a long par 5 you can birdie? Even though the finishing hole at Old Oaks plays almost entirely uphill, the recent renovation of the green complex gives a well-hit approach shot a chance to stay on the green and set up a memorable end to your round.


Hole 15 • Westchester Hills CC 

Photo By John Fortunato

​Jason Goblek tees off the 15th hole at Westchester Hills Country Club. 

Par 4 425 yards
Out-of-bounds right and a creek crossing the fairway have always made this downhill par 4 one of the more memorable holes at Westchester Hills, but the recent remodeling at the course created some spectacular views, along with two new bunkers that add some excitement to it.


Hole 15 • Siwanoy CC 

Par 4 444 yards
Siwanoy’s signature hole isn’t just pretty; it’s fun and challenging. You need a long straight tee shot to put the green in range, but a lay-up short of the creek that traverses the fairway is a perfectly respectable strategy.


Hole 6 • Scarsdale CC 

Par 5 545 yards
A gap in the tree line on the left side of the fairway gives the long hitter a chance to reach this green in two, but the conservative play to the top of the hill above the green is fun, too.


Hole 8 • Sleepy Hollow CC

Par 4 396 yards
It’s easy for an excellent golf hole to be overlooked on a course with so many standouts, and that may be the case with this mid-length par 4 at Sleepy Hollow. The tree-lined fairway is more generous that it looks, and the recent remodeling
of the green complex made the approach shot immensely more interesting.


Hole 4 • Westchester CC South 

Photo By Evan Schiller/Courtesy of Westchester Country Club

Westchester Country Club South Course, Hole 4 

Par 3 176 yards
The South Course at Westchester CC has always been known for its five picturesque one-shotters, and the recent makeover at the course made them even better. The first one you encounter, the scenic 4th hole, requires a hero shot over water to a strongly contoured green.


Hole 18 • Waccabuc CC 

Par 4 391 yards
Long-ball hitters will have a big advantage on this hole, although they deal with a downhill lie for their second shot over the pond and bunkers in front of the green. The rest of us can lay up to the left front and chip on for our par.


Hole 11 • Whippoorwill Club 

Par 3 193 yards
Few par 3s are more fun to play than a Redan. This one plays over water that adds to the aesthetic appeal of a hole where you generally aim away from the pin so the green’s slope can bring your ball to the hole.


Hole 14 • Salem CC

Par 5 595 yards
Every shot on this long par 5 is fun. The fairway off the tee is generous; the second shot requires careful shaping and distance control to get around the dogleg; the third plays over water to a steeply contoured green.


Hole 14 • Winged Foot West 

Par 4 415 yards
The closing stretch on Winged Foot’s West course starts with the 14th hole, the first of five tough par 4s that Gil Hanse’s renovation just made harder. A drive over the corner of the “shamrock” bunker now requires another 15 yards of carry, and what was once a tricky greenside trap has become a brutal cross bunker. 

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