Gil Hanse resurrects C.B. Macdonald’s ghost at Sleepy Hollow Country Club

Gil Hanse resurrects C.B. Macdonald’s ghost at Sleepy Hollow Country Club


SLEEPY HOLLOW, NY – It’s going to sweep every award this year, and it deserves it. Everything that you have heard, or will hear about the renovation of Sleepy Hollow Country Club is absolutely true. They re-perfected the golf course, and every golfer from Baja to Bangor is lining up to cheer its triumphant return to well-deserved glory.

I always used to laugh at that assessment:  when some golf course architect would come back to a course he designed, redesigned, or renovated shortly after his original work was unveiled and tell everyone he was “re-perfecting it.” One architect in particular is infamous for that line.  “Hey! [name redacted], why’d you have to go back to [name of course] so soon after you opened it?”

“I’m re-perfecting it,” he responded, smiling blithely while the entire room of golf writers looked askance.

Happily, now someone – too humble to actually say it himself – may actually have done it. It’s Gil Hanse, perhaps the most sought-after golf architect in the world right now, and he did it at no less historically important a club than venerable Sleepy Hollow.


Sleepy Hollow Country Club is as quintessential to American golf as Washington Irving’s "The Legend of Sleepy Hollow" is to American literature.

Born in the formative years of golf in this country, Sleepy Hollow is one of the earliest golf course designs of the brash, colorful and brilliant Charles Blair Macdonald (his third, to be exact). Macdonald was a blustering, brazen rakehell, but he frequently had a point. One of his bolder, louder proclamations was that American golf courses lacked the interesting strategic nuances of their U.K. counterparts, and that he was going to show us all how it was done.

He talked the talk, and then he walked the walk. He built National Golf Links of America. Game, set, match:  Macdonald.

When everyone saw how breathtaking Macdonald’s work at National was, every rich patron of the day said to himself, “I want one of those!” and suddenly Macdondald, along with his second-in-command Seth Raynor, was in great demand across the country.

In Sleepy Hollow’s case “rich patrons” is a grave understatement. It was no less a venerable triumvirate than John Jacob Astor, William Rockefeller and Cornelius Vanderbilt who came knocking on Macdonald’s door. Vanderbilt has a 340-acre estate tucked in the Hudson highlands, hard by the glorious, sun-drenched Tappan Zee beneath the noble brow of the mighty Palisades. It’s the kind of place you propose marriage to your girl. Macdonald couldn’t have asked for a better piece of property (or a deeper pocket for whom to work).

Macdonald completed his course in 1914, incorporating many of the strategic hole designs he showcased at National and that have, subsequently, become staples of the Macdonald-Raynor-Banks repertoire, but shortly thereafter land swaps, intervening architects, and a plan for a new nine holes brought significant change to his version of Sleepy Hollow. First, when four holes were sold off in a real estate deal, a local architect named Tom Winton was hired to build replacements. And then in 1930 another immortal, A.W. Tillinghast, came to Sleepy and increased the number of holes to 27. Tillinghast’s contribution included what became holes 1, 8-12 and 18 of the flagship course.


But at this point, the club had a dilemma: Macdonald’s style and Tillinghast’s clashed. The design didn’t feel like a contiguous whole, but an amalgam. To paraphrase the old Reese’s peanut butter cups commercial: two great tastes that just didn’t go together. For many decades Sleepy Hollow was never really regarded as worthy of being mentioned among the greatest designs of either architect, simply because it was half fish and half fowl, more a curiosity than a superstar. What to do?

After a 1990s renovation by a famous name resulted in a confused mélange of styles far worse than before, the Club decided they had to pick one or the other – Macdonald or Tillinghast – and renovate the course into a uniform whole. They chose Macdonald.

As Ran Morrissett wrote, “After all, Macdonald’s courses found at NGLA, Mid-Ocean, Piping Rock and St. Louis Country Club are similarly dated and [are as] prestigious clubs as Sleepy Hollow. Plus it was deemed foolhardy to try and establish Tillinghast as the prevalent design style when a) it never was and b) four of his best original designs (both courses at Winged Foot, Quaker Ridge, and Fenway) are in close proximity to the Club.”

I also credit the rise in interest in older strategic designs which has resulted in this Second Golden Age of golf course architecture (or “Platinum Age of golf course architecture,” if you prefer). Macdonald has come into vogue with the help of the Internet and a younger crop of masters like Hanse, Tom Doak, Mike Strantz, Brian Silva and many others. Macdonald in particular, and rightfully so, has a long and celebrated revival that continues to flourish to this day. Sleepy’s renovation is the sweet fruit of that seed.

So the club turned to Gil Hanse in 2005 for a master plan that would make the entire course look like Macdonald, including a complete redesign of holes 1, 8-12 and 18. Over the course of the next 13 years, they painstakingly implemented the plan he authored, along with an assist from dry cleaner-turned-golf architecture consultant and historian George Bahto. Work was completed in two parts:

  1. A period from 2005-06 where Hanse rebuilt the bunkers completely in Macdonald style, while also pulling the playing corridors and fairways to a much wider, grander scale, and
  2. A second phase from 2016-17 where he rebuilt all 18 greens to Macdonald’s shape and style, especially adding internal contour, while also increasing pinable space by a remarkable 7 percent over the course of 18 holes. The lion’s share of that amount came at the Tillinghast holes which saw a whopping 85 percent increase in size.

Fixing Nos. 1 and 18 was imperative since they are the only holes one can see from the clubhouse and, typical of Tillinghast, both were more penal than strategic. The first also presented a second issue: :ong hitters used to bomb their tee shots into the 18th fairway for a better angle to the green.  Unacceptable!


Hanse solved the problem by turning the first hole into a Leven Hole, another staple of the Macdonald repertoire. Where once the green was flat, it is now guarded on the front right side by a mammoth knoll with a dramatic tilt to the left. Now the optimum tee shot must hug the left side, dangerously close to a deep fairway bunker. The fairway also bends awkwardly at that point, so you can run through it into the rough. The green was also expanded back into a long, narrow, roughly rectangular shape with far more interesting contours and deep bunkers at the surrounds.

“I think the best improvement would be the eighth hole, now a wonderful Road Hole,” surmised a former greens committee member who spoke on condition of anonymity. “It went from an oval with a crease in the middle – a catcher’s mitt of a green, and you could only pin it up the middle - to a large Road Hole green with numerous pin positions and a gorgeous, deep bunker.”

Nos. 9-12 and 18, all Tillinghast holes, also saw similar upgrades. For the ninth, Hanse chose a Knoll hole, moving the green back and atop a knob. At the 10th, a gorgeous par 3 and the turnaround for this out-and-back routing, he recaptured 33 percent more green space and added a devilish fold in the middle, as if the long carry over water isn’t daunting enough.

The finishing stretch of the course is all-world, the rival of any club anywhere. At No. 14, the green was again expanded, from a diamond shape that tested both length and accuracy to a more rectangular shape that slopes away from the player. Hanse brilliantly added two long, parallel spines colloquially called “the Rails” which add fiendish contours and affect nearly every putt, chip, pitch shot, and approach. The 15th is one of the golf world’s great Alps hole, ascending dizzyingly to a rise, before plummeting down to a punchbowl green.


Cresting that hill, you not only see the green, but the Short Hole, the par-3 16th behind, with its new thumbprint in the center and the majestic Hudson behind. At a moment like that, who needs the Monterey Peninsula?

Look for Sleepy Hollow to skyrocket up the rankings lists once enough raters have had the chance to see it. It has everything: a strong pedigree, phenomenal terrain, ingenious greens and a wondrous natural setting. It’s easily top 30 in the country. And for once you can take a walk through the Rockefeller State Forest without having to worry about hearing hooves bearing down on you and fearsome specters seeking to bear your soul to Hell. Instead you can take them home on a flagstick for your man cave. You still get a great story at Sleepy Hollow, and you get to live to tell about it.

About the author

Jay Flemma

Starting with a blog and a dream, Jay Flemma launched his first sports-writing website in 2004. Some 13 years and 25 major golf championships later, Jay has won multiple national sports writing awards. Besides GNN, his work has appeared in numerous books as well as on-line at Cybergolf,, GolfObserver, and many other sites and print magazines. When not trying to find a lost golf ball, Jay is an entertainment, copyright, Internet, sports and trademark lawyer in Manhattan. His clients have been nominated for Grammy and Emmy awards, won a Sundance Film Festival Best Director award, performed on stage and screen, and designed pop art for museums and collectors. Jay lives in Forest Hills, N.Y., and is fiercely loyal to his alma maters, Deerfield Academy in Massachusetts and Trinity College in Connecticut.