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EMBRACING MACDONALD’S LEGACY AT SLEEPY HOLLOW

An in-depth look at the evolution of the C.B. Macdonald-designed and Gil Hanse retrovated Sleepy Hollow Country Club

“From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of Sleepy Hollow…A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.”

— Washington Irving, The Legend of Sleepy Hollow

Perhaps there was a time when the public’s consciousness of C.B. Macdonald and Seth Raynor’s work at Sleepy Hollow Country Club fit this description from Irving’s classic tale. With a retrovation of the course led by Gil Hanse now largely complete, players and architecture enthusiasts are fully awake to its greatness. In The Legend, suitors Ichabod Crane and Brom Bones vie for the heart and soul of Katrina Van Tassel, climaxing in a ghostly confrontation at a crossroads in the woods. That story foreshadows the challenge Hanse, consultant George Bahto and the club’s leadership would ultimately have to face. Standing at a crossroads, haunted by ghosts of architects past, which path would they take? By committing to recapturing the heart and soul of Macdonald’s Sleepy Hollow, they laid those ghosts to rest in a fashion that can best be described as legendary.

The Evolution of a Design Philosophy

By all accounts, Charles Blair Macdonald was a man of both feisty temperament and erudition. He was worldly and his wide-ranging interests included commerce, art, sport and architecture. Through his studies, he became aware of the work and writings of Humphry Repton, who was influential in Britain around the turn of the 19th century, coining the term “landscape gardener”. As Macdonald would later be considered the father of American golf course architecture, Repton’s publishing of The Art of Landscape Gardening in 1797 conferred upon him similar patriarchal status in his field. A passage in the book was particularly resonant with Macdonald and would send him down a path of evolution toward his distinct brand of design: “I can only plead that true taste in every art consists more of adapting tried expedients to peculiar circumstances than in the inordinate thirst after novelty, the characteristic of uncultivated minds, which from facility of inventing wild theories, without experience, are apt to suppose that taste is displayed by novelty, genius by innovation, and that every change must necessarily tend to improvements.”

Perhaps a respect for the traditions of the game and its playing fields came from time spent with Old Tom Morris in St. Andrews, but even while pushing the craft forward, Macdonald retained a connection to the unequivocal greatness of the old links. He did not believe that new and different necessarily equated to better in creative pursuits.

George Bahto, wrote the book on C.B. Macdonald, literally. In assembling his compendium of Macdonald’s life and work, The Evangelist of Golf, Bahto and his collaborator Gib Papazian illuminated the progression from a restless dissatisfaction with the quality of America’s courses to the creation of the ideal golf course at National Golf Links of America.

Another writer, Horace Hutchinson, built on the intellectual momentum of Repton when he published articles in Golf Illustrated in 1901 exploring the best and hardest holes of that time. Macdonald was affected by the articles’ premise. “These discussions certainly caught the attention of Charlie Macdonald,” wrote Bahto. “Why shouldn’t America have golf equal to that in the British Isles? In his mind, the content of the article was the definitive listing of those holes reverenced by the world’s greatest players. If America was to have golf that compared to that in Britain, its courses must be based on the same timeless genius as those across the Atlantic.”

From 1902-1906, a series of voyages back across the Atlantic ensued. With an assist from Devereux Emmet, a study was made of the greatest holes of the British Isles with the original intention of replicating them on American soil. “Now why should not one try to absorb that sanctified tradition of each hole by copying its features in another climate where in time tradition might sanctify its existence,” wrote Macdonald “The flowers of transplanted plants in time shed a perfume comparable to that of their indigenous home.” The plan to transplant holes morphed into a distillation of the strategy and features that could be drawn upon to create new courses. Bahto described that shift of focus, “It became clear to Macdonald that his original concept of topographic duplication was not as relevant to the quality of the course as the individual strategic elements.”

The land on which The National was built was optimal for Macdonald’s first experiment with his ideal concepts approach to design. It shared characteristics with traditional linksland—unforested, with topographical movement that was interesting, rather than severe. The project also fortuitously connected Macdonald with Seth Raynor. The combination of the former’s ideas with the latter’s surveying and engineering brilliance, applied to that land, resulted in a masterpiece. But what about more “peculiar circumstances”, as Repton put it? Would the approach hold up on wilder terrain? The duo’s next three projects at Piping Rock, St. Louis Country Club and Sleepy Hollow, which opened for play in 1914, proved that the ideal concepts could be applied to great effect on any site.

The original course explored the slope, the ridge and the valley, with the greater portion on the clubhouse side. Although the routing stayed mostly close to home, there was an adventurous spirit to the manner in which Macdonald and Raynor laid their ideal holes out on the dramatic landforms. Their creation was well received, but it would not take long for the course at Sleepy Hollow to begin evolving away from this starting point.

Calling in the Cleaner

How did a man who was a dry cleaner by trade become the foremost authority on the work of one of the Golden Age masters? Serendipity, or rub-of-the-green, had a strong hand in George Bahto’s story. He took up golf as an adult in New Jersey and found himself drawn to courses with bold features. Curiosity about the who, how and why behind his favorite holes and courses led him to the discovery of Charles Banks. Research on the protege Banks uncovered the mentor Seth Raynor, which subsequently brought him to Charles Blair Macdonald. The men’s creative approach fascinated Bahto, and down the rabbit hole he went, resulting in an avocation as a golf architecture historian.

Bahto connected with Gil Hanse, who got him involved in his first construction project at Stonebridge Golf Links, a course that drew some design inspiration from the philosophy of Raynor. It would not be his last. In writing The Evangelist of Golf, George Bahto enlightened the world on the value of C.B. Macdonald’s approach to design. He cleaned up Macdonald’s image, and the thinking of many club Green Committees who had been directly or indirectly degrading his courses for decades. It should therefore come as no surprise that some of those clubs would turn to Bahto for counsel, including Sleepy Hollow, which brought him on as a consultant.

It is worth noting that in all of Bahto’s writing about Charles Blair Macdonald, one word is conspicuously absent. That word is “template”, which has become shorthand when referring to the holes Macdonald, Raynor, Banks and others created using the ideal concepts. Unfortunately, the term carries with it the potential for an intellectually lazy inference that Macdonald and Raynor’s design process was somehow akin to dumping out a bag of cookie cutters and arranging them willy nilly across the landscape. The strength of each of the holes at Sleepy Hollow, with their strategically placed hazards and wondrously varied greens, is evidence that any downgrade to the ideal concepts approach as involving shortcuts is entirely off-base. The application of timeless and proven design elements to a unique landscape is more demanding because the architect is choosing to adhere to a constraint. There is no bailout, and no acceptance of inclusion of weak holes on a course. Bringing the course back up to Macdonald’s higher standard, and his constraints, was the challenge that would occupy Gil Hanse and his team for more than a decade.

The Retrovation

By the time that Gil Hanse found himself standing at a design crossroads with George Bahto at Sleepy Hollow, he had already traveled a long road to gain an understanding and appreciation for the architectural roots that gave rise to America’s Golden Age. He followed in Macdonald’s footsteps by taking an extended study trip to the British Isles, returning to initially work for Tom Doak before venturing out on his own. In 2003, as Hanse Golf Design was beginning to gain momentum, Hanse contributed an essay entitled “Stop Making Sense!” to Paul Daley’s Golf Architecture: A Worldwide Perspective in which he shared a point of view that at first glance seems discordant with respect for Macdonald’s philosophy.

“The use of natural landforms to create interesting and creative golf holes should not be held to any formulas,” wrote Hanse. “If a rule must be stated, it should be that no rules apply to the use of a landscape to create playing grounds for golf. The golf course architect should be creative in utilizing natural features to dictate the strategy of the course. Inherent in the unique character of every site are unique golf holes just waiting to be discovered. Is this not the true challenge of golf course architecture, to build fresh and innovative holes that derive their beauty, playability, and interest from their natural surrounds?”

Repton might have raised an eyebrow reading those words. There are certainly times when exercising one’s creative license courageously involves blazing a new trail. Making the choice to honor tradition is not mutually exclusive with creative freedom by default though. As it turned out, Hanse’s focus on working from the ground up, coupled with his reverence for the Golden Age, was exactly the remedy needed to cure Sleepy Hollow’s ills. Over the years since Raynor completed the original eighteen, the course had changed considerably. New holes were created by Tillinghast and others when land was sold and the club expanded to 27 holes.

The expanded 27-hole routing after Tillinghast’s addition

More recently, other architects and green committees without the benefit of Bahto’s knowledge of Macdonald made further modifications that altered hole strategies and aesthetics for the worse. The initial wave of retrovation focused on consistency of style, primarily of the bunkering, prioritizing the Tillinghast holes. Those phase one changes having been well received, Hanse and the club’s leadership decided to fully embrace Macdonald’s ideal concepts. This decision was momentous at two levels. First, they were removing the work of A.W. Tillinghast in the Westchester neighborhood where he reigns supreme. Second, they were choosing to accept Macdonald’s standard for greatness. They were all in.

“Deciding to remove the work of Golden Age architects, especially one as prolific as Tillinghast, is always a difficult choice,” explained Hanse’s associate Ben Hillard, who worked extensively on the Sleepy Hollow retrovation. “If you consider golf architecture in Westchester County, Macdonald & Raynor have one course and Tillinghast has a handful, including a couple of masterpieces. With the bulk of the holes to be restored/renovated being Macdonald & Raynor, a more cohesive course could be made by taking the Tillinghast holes and replacing them with holes like ‘Road’, ‘Knoll’ and ‘Double Plateau’, some of which had been lost when the club sold land to the North side of the property in the late 1920s.”

It would not be enough to simply add those features and holes back into the mix, however. They had to do so in a manner that would fit the land as well as if the Macdonald and Raynor had done it themselves. In being attuned to the landscape at such a high level, Hanse was able to channel the true genius of Macdonald’s ideal concepts. The Leven 1st, Road 8th and others are new, but could easily be mistaken for originals. The remaining holes were brought even further into line with the ideals. The following montage of the Short 16th illustrates the extent of the transformation over time.

The original short – Credit: Simon Haines

Before the retrovation began, with misfit bunkering – Credit: GolfClubAtlas

After phase one of the retrovation with trees removed, bunkering and green partially restored

Excavation of the tee and green surface begins – Credit: Ben Hillard

Restoring the thumbprint – Credit: Ben Hillard

Grassing the newly shaped putting surface – Credit: Ben Hillard

Gil taking in the finished product – Credit: Ben Hillard

Bunker and thumbprint fully retrovated

A place where magical moments happen at Sleepy Hollow

Like Macdonald and Raynor, George Bahto would sadly not be alive to see this current, magnificent iteration of the course that began a century ago. The spirit of all three men and their ideals can be found in the completed work of Hanse and Hillard, and one can safely surmise that generous praise and approval would be forthcoming.

The Course

“…there is a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose; and the occasional whistle of a quail or tapping of a woodpecker is almost the only sound that ever breaks in upon the uniform tranquillity.”

Washington Irving, The Legend of Sleepy Hollow

Click on any gallery image to enlarge with captions

The club takes its name from the Pocantico River valley in which it sits. The Dutch name for that river was Slapershaven, or “sleepy harbor”. Although it might have accurately described their maritime activities, “sleepy” is not an adjective that applies to the land the course traverses.

Arriving at the grand front gate, visitors are immediately aware that an awe-inspiring experience awaits. The drive up to the mansion that now serves as the clubhouse provides tantalizing glimpses of golf holes arrayed across the hillside. After a warm welcome from staff and members alike, players walk onto a porch with stunning views of the Hudson River and Palisades of New Jersey beyond. Before striking the first shot of the day, the spirit is already soaring.

The first two holes bring players up the western side of the ridge that serves as the anchor feature in the routing. The 3rd through 15th explore the terrain high and low on the eastern side. The iconic 16th returns players to the top of the ridge, from which the final two holes return home. A loop around Sleepy Hollow has a literary quality that would make Irving proud. The story builds in a broad arc toward climax, interspersed with moments both dramatic and quietly sublime.

The Hanse retrovation unified Sleepy Hollow, and Superintendent Tom Leahy and his team continue to refine and present it beautifully. It is a highly cohesive golf course comprised of eighteen holes, each worthy of study and appreciation. To allow for an examination at depth, the tour that follows includes original sketches by Gil Hanse (@Gil_Hanse), the artwork of Tom Young (@BallparkBlueprints), the photography of Jon Cavalier (@LinksGems) and commentary from Ben Hillard (@Ben.Hillard). Playing the course has a wonderfully transportative effect—we invite you to get similarly carried away as you read on.

HOLE #1 “Leven” – 418 yards – par 4

The 1st is finally a worthy start to this golf course. Gil Hanse knocked down trees and opened better views, and turned a flat, boring green into a wild one. Though it doesn’t get the publicity that some of the other holes do, this is low-key one of the most improved holes on the course. “This hole was not in either of the first two renditions of the golf course and was built at some point in the 1930s,” explained Hillard. “We transformed it into a Leven by introducing a whole new strategy to the hole. Golfers are encouraged to play towards or past a big bunker on the left edge of the fairway to provide the best angle into the green which is protected by a mound short right.”

HOLE #2 “Climbing” – 372 yards – par 4

The short par-4 second is a transition hole—it’s main purpose is simply to take a player from the bottom part of the course to the upper shelf. These kinds of uphill transition holes are usually rather boring, but this is one of the better versions of its kind, thanks to an exciting green sloping hard back-to-front and a deep bunker front right. This is a birdie opportunity, but it’s also a hole that can bite the careless player. We speak from experience when we say that you can be on this green in two, in the front bunker in three and walking off with a triple before you know what happened.

HOLE #3 “Eden” – 172 yards – par 3

The 3rd is the first of Sleepy’s brilliant foursome of par-3s, and maybe the best of the bunch. With a panoramic view of the Hudson at your back, you play over the ravine to a huge, sloping green protected in front by a deep Strath bunker. Hanse’s restoration of this green opened up an infinite number of outstanding hole locations, and it’s not uncommon to have a putt that breaks more than 10 feet.“The green for the third hole originally played as a blind ‘Alps’ from somewhere near the current 5th tee area,” recounted Hillard. “This can be seen in the earliest plans of the course. At some point the hole changed to being the mid-length par-3. Although called an Eden it lacked the proper characteristics. The decision was made to build an entirely new green and bunkers for the hole—only the very deep bunker on the right hand side of the green was original.”

HOLE #4 “Headless Horseman” – 415 yards – par 4

Be sure to take in the view of the famous 16th and the river behind and check the pin location on the blind Punchbowl 15th, then try to avoid the fairway bunker up the right. Long tee shots will clear the ridge and offer a view of the skinny, deep green, which was expanded by Hanse’s crew. The connected complexes and shared bunkers of the 4th and 14th are a personal favorite.

HOLE #5 “Panorama” – 435 yards – par 4

Another strong par-4 on the front side, and a LinksGems favorite. The tee shot over the hill is completely blind, and players need to stay to the right to avoid rolling out into the rough on the left. Cresting the hill in the rolling fairway is one of the great visual reveals in all of golf, and the uphill approach to this infinity green is among the most exciting shots on the course. The putting surface has been significantly expanded to the right and the views from this spot are some of the best on the property.

HOLE #6 “Lookout” – 475 yards – par 5

The first of only two par-5s at Sleepy, the 6th is an eagle opportunity if you can manage to put your drive in the upper fairway—easier said than done. A Principal’s Nose bunker guards the layup zone, and the green itself is canted sharply front to back. If you’re trying to hang a number, you need to make no worse than five here. “One of the coolest Macdonald/Raynor green complexes we’ve ever seen,” gushed Hillard. “George Bahto said that he’d never seen a Macdonald green like it.”

HOLE #7 “Redan” – 221 yards – par 3

The 7th holds the place of LinksGems all-time greatest reverse Redan. It plays steeply downhill to a green sloping HARD away toward the back right. Right-to-left shot shapes can attack the green directly, but a straight or left-to-right tee shots must use the slope. Shots played to the fairway left of the green will tumble all the way down to the right side of the green. Recent tree removal has brought the wind back as one of this hole’s many defenses and the green has been expanded to allow for additional hole locations.

HOLE #8 “Road” – 488 yards – par 4

This monster par-4 is the toughest on the course. Hitting the hog’s back fairway is a must, as players will then need to contend with the treacherous Road Hole bunker guarding this green front left. It looks big and plays bigger than that. Par here is a great score. “We converted this Tillinghast hole to a Macdonald ‘Road’, repurposing the existing hog’s back in the fairway, which adds a layer to the strategy of the hole,” said Hillard.

HOLE #9 “Knoll” – 424 yards – par 4

“The fairway bunkers on the 9th are truly penal, and any shot that misses the green left is in major trouble. The green itself—one of the few cut off from the fairway by a section of rough—can play relatively easy when the pin is up front, but is much tougher when the hole is cut on either of the back tiers. This is one of the most improved holes on the course. “We converted this one to a ‘Knoll’ with rough across the approach, which was a bit of a bold choice but it separates the playing and visual characteristics of the 9th and 11th holes,” Hillard elaborated. “We were particularly excited about how the 8th and 9th turned out, especially when looking down the two holes from the halfway house.”

HOLE #10 “Lake” – 168 yards – par 3

The 10th is a picturesque par-3, and the only hole at Sleepy Hollow with water near a green. “This is an all new green expanded out to the lake edge,” detailed Hillard. “We lowered it to make the green expansion work.” The two sets of tee boxes—one attached to the back side of the 9th green and the other short and left of it—combined with the huge spine installed in this green by Gil Hanse allows the 10th to play like four different holes in 1, depending on the day’s hole location. Putting across the spine is a lot of fun but not very healthy for your score.

HOLE #11 “Ichabod’s Elbow” – 433 yards – par 4

This par-4 favors a left-to-right tee shot, as it’s no fun trying to hit a long iron into this volcano green if the drive doesn’t get far enough up the fairway. It’s really a ‘hit it or else’ proposition—anything short will roll all the way back to the fairway, a miss left or right catches the deep bunkers (if you’re lucky), and if you go long, you might just want to keep walking into the clubhouse.

HOLE #12 “Double Plateau” – 536 yards – par 5

The second of the two par-5s and the first hole substantially changed by Gil Hanse, the 12th used to play as a hard dogleg par-4 to a green along the woods line. Hanse turned the hole into a beautiful par-5 playing through a rocky valley and over a winding creek to a beautifully designed Double Plateau green. “The Tillinghast green is still visible short and 100 yards right up on the hill,” Hillard said. “We also formalized the meandering brook to help with drainage and add strategy to the hole.”

HOLE #13 “Sleepy Hollow” – 408 yards – par 4

The 13th is the LinksGems selection for most underrated hole on the golf course. The ridge in the fairway hides some terrific squared off bunkering up the left side, while the green is guarded by one of the deepest bunkers on the course. As on the 11th, there are few good misses here—the little bunker in the face of the rise helps players more than it hurts them. “Very soft alterations were made to the front of the green to expand the pinnable area closer to the false front,” added Hillard.

HOLE #14 “Spines” – 414 yards – par 4

The par-4 14th marks the beginning of a four hole run from the highest point on the property to the lowest. Staggered cross bunkers make this an exciting tee shot, but the green is where the fun really begins. Formerly an unremarkable complex, Hanse restored two spines running from the back of this green toward the front, effectively chopping the huge putting surface into three smaller ones. “The original Macdonald green was manipulated at some point and significantly reduced in size,” Hillard explained “In looking at some aerials of the golf course from the 1924 aerial, we found a larger squared green with two spines running from the back well beyond the center that were begging to be recreated.” It is now in the realm of possibility to be on this green in regulation and make double.

HOLE #15 “Punchbowl” – 502 yards – par 4

With the exception of the 4th at Fishers Island, this is the LinksGems favorite Punchbowl. Blind from everywhere, the green can be hit directly, but players who aren’t long enough to make the full carry can land approaches 50 yards short up the left side and use the chute to bounce a shot into the bowl. When the hole is cut on the little shelf on the left edge of the bowl it plays a full shot harder. “We made minor edits to the green to introduce more pinnable space,” detailed Hillard, “and completed the punchbowl to ensure all balls that make it over the hill find their way onto the putting surface.”

HOLE #16 “Short” – 149 yards – par 3

One of the most photographed holes in the world (due in no small measure to LinksGems), this par-3 is as memorable as they come. From an elevated tee over a ravine to a square green ringed with sand and featuring a deep thumbprint, with the Hudson River and the Palisades below and beyond, this is like playing golf in a postcard. “Working off of an old photo from the club’s archives as well as what we saw in the ground, we figured that the original green had been manipulated at some point but not completely rebuilt,” said Hillard. “The horseshoe was still there, but the surface either side of it had been filled in. The high point of the horseshoe was identified and then we delicately removed that extra material to expose the original contours—an incredible moment for a shaper.” When the pin is in the middle, you’re thinking of making an Ace, but the real fun is playing to a pin on one of the edges—the green is pinnable to all eight sections outside the thumbprint.

HOLE #17 “Hudson” – 446 yards – par 4

On most courses, this hole would be the signature, but even after the 15th and 16th, the par-4 17th with a bridge and harbor view still impresses. The sharply canted fairway plays games with your head—the line is farther left than you think, and the bunkers down the right catch everything. The large green, which was expanded by Hanse’s team, makes the distance of the approach hard to judge. Trust your caddy, it’s farther than it looks.

HOLE #18 “Woodlea” – 426 yards – par 4

“This hole was built at the same time as the 1st hole in the ‘30s. A new, larger green was built inspired by Macdonald and Raynor, featuring a large false front and much flatter rear tying into the clubhouse steps,” concluded Hillard. “It sits much better on the landscape.” Playing back up to the mansion, this is your classic gut punch par-4 finisher—it will make your earn your match. The large tree on the right is murder on leaking tee shots, and the false front rejects indifferent approaches. The new back right section of this putting surface makes for some tough but fun recoveries, especially when the patio is crowded. A fitting finish for one of the greatest courses in the world.

Stories are often told of the great artists reaching inflection points in their work. Those moments when they can stay in their comfort zones or push forward into new territory. To leave a legacy requires the courage to take the latter path. In embracing the philosophy of C.B. Macdonald and Seth Raynor at Sleepy Hollow, not only did Gil Hanse evolve as an artist, he left a legacy for the membership and the game at Sleepy Hollow. The Legend’s author sums up best the impression left on the fortunate by a visit to this special place.

“If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.” 

Washington Irving, The Legend of Sleepy Hollow

Copyright 2019 – Jason Way, GeekedOnGolf


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Sleepy Hollow Course Tour by Jon Cavalier

SLEEPY HOLLOW COUNTRY CLUB – A COURSE TOUR & APPRECIATION

Scarborough-on-Hudson, NY – C.B. Macdonald, Seth Raynor, A.W. Tillinghast

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Full disclosure: I love this place.  Sleepy Hollow is, quite simply, one of my favorite places in the country to play golf.  Exceptional golden age architecture, spectacular views, exciting shots, fabulous conditions — Sleepy Hollow has everything a golfer could want.  And to top it off, Sleepy Hollow is the course that sparked my interest in the work Charles Blair Macdonald and Seth Raynor, and subsequently my love for golf architecture generally.  So I’m biased.

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15th and 16th Greens

And of course, I’ve been wanting to do a photo tour of Sleepy Hollow for quite some time.  As with my tour of Old Town Club, Sleepy Hollow’s recent near miss on Golf Digest’s Top-100 list provided a perfect impetus and incentive to pull this tour together and shine a bit of a light on a place that, for me, is ranked about 100 spots too low.

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The “lesser” of the par-3s at Sleepy Hollow

The photographs you see below were taken over the course of two visits to Sleepy Hollow (which is the reason for the differences in light, course conditions and pin positions).

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Waking up at Sleepy

I hope you enjoy the tour.

SLEEPY HOLLOW COUNTRY CLUB

Sleepy Hollow was built on the 338-acre Woodlea estate, which the club acquired in 1911.  C.B. Macdonald designed the golf course, with Seth Raynor on the ground as engineer, and the original 18 holes were completed that same year.  In the late 1920s, AW Tillinghast expanded the course to 27 holes, creating several new holes for the 18-hole “Upper” and 9-hole “Lower” courses.  Via the passage of time and the intrusion of several interim architects of more modern vintage, the course lost touch with its golden age roots for a period.  George Bahto and Gil Hanse were brought in to restore the course’s rightful Macdonald heritage.

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The result speaks for itself.  In its present form, the main course at Sleepy Hollow is rife with beautiful interpretations of many of the Macdonald templates, including Redan, Punchbowl, Double Plateau, and one of the most gorgeous Shorts this side of Fishers Island.  While the property has been owned by Colonel Eliot Shepard and William Rockefeller, and the course has been worked on by some of the great architects in golf, including Tillinghast and Hanse, Sleepy Hollow today stands clearly as a shining example of CB Macdonald’s design tenets and as a fitting monument to George Bahto.  Quite a lineage.

The Clubhouse

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No tour of Sleepy Hollow is complete without at least a brief discussion of its magnificent clubhouse.  Some of the best courses in the country are identifiable by their clubhouses alone, and in a few instances — Winged Foot, Oakmont, Myopia Hunt, Ridgewood, and Shinnecock, to name but a few — they become iconic in their own right.  Sleepy Hollow’s is one such clubhouse.

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Looming high above, the clubhouse, designed by Stanford White in 1893 as the manor house, is the first thing the golfer notices about Sleepy Hollow upon entering the gates, and it provides quite the first impression.  As the long entrance road makes way up toward the building, the loping route provides views of several holes on the lower course, the driving range, the stables, and the many rock formations that remind the golfer that he’s in Westchester.  But all the while, the presence of the massive clubhouse dominates.

The entrance road culminates at the south face of the clubhouse, seen in the photo below.  The parking lot is in the rear, to the right.

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The clubhouse has been the scene of several television shows and movies, and has hosted countless events.  And with views like this from its spacious lawn, it’s easy to see why.

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It is a beautiful building and a fitting way to begin a day at Sleepy Hollow.

The Scorecard, Logo and Haunted Bridges

A golfer senses a theme at Sleepy Hollow.  The club has named each of its holes in reference to Washington Irving’s story, which was set in the surrounding hills.  The course itself stretches to 6880 yards and plays quite pleasantly at 6377 yards from the white tees (which I use for this tour) to a par of 70.

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The club’s logo of the Headless Horseman, likewise taken from the Irving story, is one of the best in golf.

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Finally, the Haunted Bridges, encountered on the 3rd, 10th and 16th holes, appear to have been built by Irving’s contemporaries and provide a unique and fitting touch.

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THE GOLF COURSE AT SLEEPY HOLLOW

Hole 1 – “Sunnyside” – 406yds – Par 4

There is no more enjoyable way to start a round of golf that from a first tee that sits in the shadow of the clubhouse, as is the case at Sleepy Hollow.  The Hudson river just peeks out above the treeline, giving the golfer a small taste of what’s to come.

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The first hole is a downhill dogleg right which, while tree lined, has a more generous landing area and more room to work the ball than it first appears.  The ideal position is the left half of the fairway.

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The first green is of a good size, but the bunkering on both sides and the visually deceptive framing bunker short left make for a challenging first iron.

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The fairway runs seamlessly into the green, allowing for the ball to be run on to the putting surface, but the green slopes up from front to back.  The deep Macdonald bunkering is felt immediately.

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The view back up the first hole — steeper than it appears, and a solid start to what will become a memorable round.

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Hole 2 – “Outlook” – 321yds – Par 4

Reminiscent of the first hole at Myopia, the second hole is a short, uphill par-4 defended by a relatively severe, well-protected green.  The “eyeglasses” bunkers short of the fairway are not in play, but make for an appealing visual effect.

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The approach to the second green will almost always be from an uphill lie, making for frequent short-right misses.  This deep-and-steep wraparound front-right bunker is waiting to catch those misses.

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The climb to the second green at Sleepy Hollow is the first point on the course where the golfer is treated to both the stunning views of the Hudson River . . .

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. . . and to the sight of Sleepy Hollow’s one-of-a-kind walking bridges.  This is the point in the round where the golfer knows, beyond a doubt, that a special day awaits.

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Hole 3 – “Haunted Bridge” – 153yds – Par 3

Aptly named, the third hole may be the best par 3 among the standout collection of one-shotters at Sleepy Hollow.  Played over a deep ravine to a green elevated just enough so that the golfer cannot see the entire putting surface, the third provides one of the most exciting tee shots on the front nine at Sleepy Hollow.

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The way in which the land was sculpted and the third green was benched into the hill will appeal to even the most jaded GCA enthusiasts.

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To access the green, the golfer crosses the Haunted Bridge for the first time.  Simply beautiful.

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Hole 4 – “Brom Bones” – 404yds – Par 4

Cresting the hill after putting out on the third green, the golfer is afforded a wide view from the fourth tee over a large, open section of the golf course.  The fourth hole plays out to an open fairway that dips down, then crests a small rise before arriving at the green.

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Longer shots may clear the rise, offering the golfer an unobstructed view of the putting surface.  For those that do not, an aiming marker is provided behind the green.

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A precision approach shot is required, as the fourth green is well guarded with deep bunkers, and is itself riddled with undulations, allowing for difficult pin positions.

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Hole 5 – “High Tor” – 403yds – Par 4

Playing back in the direction of the fourth tee, the fifth hole plays over the rise in the fairway (which is an easy carry for all players), then drops quickly before again rising to meet the green.  The view from the crest of the rise is spectacular.

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The encroaching bunkers, which begin well short of the fourth green, provide for an added challenge on the player’s approach.  Shots that come up short are in danger of rolling several yards back down the fairway.

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Approaches that come up short face this shot, with only the green (with its false front and varying internal mounds) and the pin in view.

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The fifth green.  No words necessary.

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Hole 6 – “Headless Horseman” – 458yds – Par 5

The first three shot hole at Sleepy Hollow is short on the card but plays longer, thanks to the hill that must be climbed before reaching the second fairway.  Aggressive, longer hitters can carry the steep, mounded wall but many players are better off simply laying up short of it.  Right is dead, and the massive grass bunker on the left side of the hill just wishes it was dead.

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Once reaching the upper tier of fairway, the golfer must contend with the principal’s nose bunkering, which sits smack in prime lay-up territory some sixty yards short of the green.

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The sixth green slopes substantially from back to front — approaches that end up beyond the hole will result in a very tricky putt back down to the hole.

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Hole 7 – “Tarry Brae” – 193yds – Par 3

In your author’s humble opinion, the best downhill reverse-redan hole in existence.

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The steepness of the green from high left to low right is so pronounced that balls routinely roll for 30 seconds or more as they funnel down toward the pin.  A wonderfully exciting hole to play.

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Hole 8 – “Sleepy Hollow” – 439yds – Par 4

The eighth hole begins the stretch of holes that were originally laid out by Tillinghast, and which are, for the most part, on a flatter, narrower portion of the property.  Nevertheless, the rolling terrain provides for many interesting shots, as first seen on the par-4 eighth hole.  Off the tee, the preferred result is the left side, but the partially hidden low left fairway bunker must be avoided.  A large mound in the right half of the fairway can scatter balls in any direction.

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The eighth green is set perfectly among the hills and rocky outcroppings.  A false front repels indifferent approaches.

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The eighth green, with the eleventh green complex visible behind.

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Hole 9 – “Katrina’s Glen” – 377yds – Par 4

The ninth provides a generous landing area for tee shots, but balls that end up short and right will face a blind approach to a small, well defended green.

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Tee shots that find the high left side of the fairway will have the preferred look down the center of the slightly elevated green.

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As shown in this photo, missing left is bad, but missing far left is awful.  Note the many appealing pin positions in the rippling green.

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Hole 10 – “The Lake” – 136yds – Par 3

As noted above, the 10th is probably the “worst” of Sleepy Hollow’s four one-shot holes, which should tell you everything you need to know about the high quality of the quartet that the course presents.

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The only hole at Sleepy Hollow with a true water hazard (the 12th has a small stream crossing it), what you see is what you get . . .

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. . . but it sure is pretty.

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Hole 11 – “Ichabod’s Elbow” – 371yds – Par 4

The offset teeing ground of the eleventh hole, benched into the side of the hill bordering the property, creates a soft dogleg right which favors a cut first shot.  While there are rugged, wooded areas on both sides of this hole, even bad shots are typically found and played.

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The eleventh’s key feature is its elevated green and surrounding green complex.  As you would expect, the elevation of the green makes the bunkers much deeper and much more penal as a hazard.

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The green is also one of the most undulating on the golf course . . .

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. . . and this raised section in the right rear of the putting surface makes for both some interesting putts and some impossible recoveries from misses left.

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The wonderfully constructed eleventh green complex, as viewed from the left side.

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Hole 12 – “Double Plateau” – 513yds – Par 5

The second and last par 5 at Sleepy Hollow, the twelfth winds left between the varied hills and mounds that mark this section of the golf course.  This hole was one of the most modified by Bahto and Hanse, and it is safe to assume that Macdonald would approve.

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The hole is reachable in two by longer players capable of positioning their tee shots in a spot that allows the dogleg to be negotiated.  Those laying up must contend with a small stream that winds across the fairway a few dozen yards short of the green and down the left side of the fairway.

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The three-tiered double plateau green is exceptionally built and, while severe in spots (as it should be) it is also large enough to accommodate accessible pin positions.  The steep fairway-cut slope fronting the green adds another layer of challenge, especially to front pins.

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A look back down the twelfth hole.

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Hole 13 – “Andre’s Lane” – 384yds – Par 4

The thirteenth marks the golfer’s return to the area of the course originally developed by Macdonald, and it’s an excellent hole.  A wide, gently inclined fairway slopes gently from high left to low right, and while a line up the left side is ideal, it also confronts two fairway bunkers and a cross-hazard. A line up the right is safer, but not only risks caroming into the rough, but also requires an approach from a less-than-ideal line over perhaps the deepest bunker on the course.  At Sleepy Hollow, such risk/reward decisions are confronted on a continual basis.

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The raised thirteenth green complex is one of your author’s favorites.  In addition to the extremely deep front right bunker, the complex features a pot bunker cut front left, along with a large expanse of fairway cut that extends well to the left of the green before culminating in a kick-slope that tumbles to the putting surface.  This unique setup allows for players to play safely away from the righthand bunker and either benefit from the built-in slope or to putt from above the left side of the green.  An old stone wall frames the rear of the green.  A wonderfully designed feature.

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The thirteenth green as viewed from the fourteenth tee, showing the large area of fairway cut grass.  Putting from up there is both challenging and fun.

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Hole 14 – “Homeward Bound” – 378yds – Par 4

Yet another aptly named hole, the fourteenth tee is set at the eastern corner of the property, the farthest point on the course from the clubhouse, and the next five holes stretch across the property and return the golfer home.  The tee shot on the fourteenth appears simple but is deceptively complex.  From the tee, the righthand bunker juts into the rising fairway. But this small hill not only obscures the green . . .

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. . . but hides a similar, though larger, lefthand cross bunker that sits just beyond the high point of the fairway.  The firm conditions and the now-downhill slope of the fairway will carry most balls that crest the hill left of center into this bunker.

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The fourteenth culminates in a narrow, deep green – one of the smallest on the course.  The green slopes relatively gently from front to back before abruptly ending and falling several feet to a right rear bunker or the rough below.

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From the right side, the golfer is treated to a long view of the green, the multi-tiered bunkers that separate the fourteenth and fourth greens, and the ever-present rocky surrounds of Sleepy Hollow.

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Hole 15 – “Punch Bowl” – 437yds – Par 4

The fifteenth is your author’s favorite hole at Sleepy Hollow, and it is fantastic.  An Alps/Punchbowl amalgamation, the combination of features found on this hole are unique in my experience, and together, they combine to form one of the most exciting, rewarding golf holes that I have ever played.  From the slightly elevated tee, only the first 400 yards of fairway are visible to the golfer, along with the right fairway bunker.

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The fairway is generous but canted rather substantially from high left to low right.  The left side of the fairway is ideal, and anything right of center runs a high risk of catching the right fairway bunker.

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The long approach shot is entirely blind, as the green sits some 20-30 feet below the fairway.  The perfect shot is played out over the right hand bunker, left of the aiming flag. As the golfer crests the fairway . . .

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. . . he is rewarded with the breathtaking view of the punchbowl green, with the sixteenth green behind and the Hudson River valley far below.

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Looking back, the proper route to the green is revealed.  One could never tire of playing this magnificent hole.

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Hole 16 – “Panorama” – 150yds – Par 3

One of the most beautiful one shot holes in the country, the Short at Sleepy Hollow plays back over the gorge that was first confronted on the third hole to a green ringed almost completely by a trench bunker.  The club has wisely removed all of the trees that once marred this spectacular view.

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Gorgeous from any angle, the sixteenth’s views hide a surprising amount of slope within its putting surface.

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The golfer again crosses the Haunted Bridge over the gorge on his way to the sixteenth green.  The way that the third and sixteenth holes were laid out over this terrain is a brilliant example of an architect making the most of a unique but difficult feature.

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Hole 17 – “Hendrik Hudson” – 433yds – Par 4

The seventeenth plays shorter than its yardage, as tee shots will roll forever.  Given the heavy cant of the fairway from left to right, however, care must be taken to properly place one’s tee shot or risk it rolling into the right rough for the cluster of fairway bunkers which are just out of view below the crest of the hill.

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The cluster of righthand fairway bunkers, as well as the extended fairway, are revealed as the golfer descends the seventeenth fairway.  The firm, fast conditions make these bunkers play far larger than their footprint.

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Level lies on approach are few and far between, making this narrow, bunkered green a difficult target.  The fairway runs seamlessly into the front of the green, however, leaving the option for a ground attack open.

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The greenside view of the long downhill penultimate hole.

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Hole 18 – “Mansion Rise” – 401yds – Par 4

While the seventeenth plays shorter than its yardage on the card, the eighteenth, leading back up to the iconic clubhouse, plays much longer than its listed 401.  While tee shots up the left side of this relatively narrow fairway will bounce down into ideal position, the lefthand fairway bunker must be avoided, as it makes reaching the green (or anywhere nearby) a virtual impossibility.

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The beautiful approach shot with the clubhouse directly behind the green (and, often, the lunch crowd observing play) provides one last pleasant memory of a golfer’s round.  While getting up and down from a left miss is tough, missing right can lead to a 30 yard uphill pitch.

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The green, following the slope of the land, is pitched substantially from back left to front right.  Putting back to a front pin is a challenge.

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Like the first tee, the final green at Sleepy Hollow sits mere steps from the clubhouse.

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Sleepy Hollow is a must not only for any fan of CB Macdonald, but for anyone with a love for golden age golf architecture or just a love of fun, exciting golf.  Head Professional David Young, Superintendent Tom Leahy and the club’s members are rightfully proud of their golf course and have acted as outstanding custodians of this treasure.  Soon, as more raters see Sleepy Hollow in its current form, it will assume its rightful place on every top 100 list there is.  But until then, it remains an underrated gem that everyone should try to see at least once.

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Pops lets fly on 16

I hope you enjoyed the tour.


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Copyright 2017 – Jason Way, GeekedOnGolf