The Legends of Sleepy Hollow

— The Logo

The story starts in 1790. Washington Irving, one of the first giants of American literature, wrote of a young schoolmaster named Ichabod Crane courting the lovely Katrina Van Tassel, the daughter of a wealthy farmer in the New York hamlet of Sleepy Hollow. Abraham “Brom Bones” Van Brunt, the town bully, also is in love with Van Tassel, and he harasses Crane with a series of pranks.

One autumn evening, during a harvest party, Brom tells the story of the Headless Horseman, the ghost of a soldier who was decapitated by a cannonball during the Revolutionary War and rises from his grave in Sleepy Hollow every night to search for his missing head. At the same party, Crane finally asks for Van Tassel’s hand. She rejects his proposal, and the heartbroken Crane begins his lonesome ride home on a plow horse named Gunpowder.

As Crane makes his way through the misty night, a cloaked rider comes rumbling up fast from behind. Convinced it’s the Headless Horseman, Crane rides for his life. Approaching a bridge, the ghostly pursuer hurls at Crane what appears to be his head, knocking the spindly teacher to the ground. The next morning, Gunpowder is seen near Crane’s gate. A shattered jack-o’-lantern is found close to where Crane took his spill. But no one ever sees Crane again—he has fled Sleepy Hollow for good. Despite suspicion, no one is able to prove that Brom Bones was disguised as the Headless Horseman. 

Irving’s tale immediately became part of the American storybook, and it’s been adapted countless times over the decades, from a Will Rogers movie in 1922 to a Disney cartoon in 1949 to a Tim Burton feature film in 1999.

Naturally, Sleepy Hollow Country Club made the Headless Horseman its logo, which has consistently been recognized as one of the most iconic in the game. Meanwhile, some older members still wink and claim that the Headless Horseman fired his fateful projectile at Crane near the bridge connecting the tee and green on the par-3 third hole.

— Woodlea

Ground was broken in 1892 on Woodlea, a 75-room Victorian mansion on 500 picturesque acres overlooking the Hudson River. It was to be the home of Colonel Elliott Fitch Shepard, a lawyer who led the founding of the New York State Bar Association in 1876, and his wife, Margaret, the granddaughter of Commodore Cornelius Vanderbilt.

The estate was built by Stanford White of the architectural firm McKim, Mead & White. It was the most important American firm of its day, with Penn Station, the main campus of Columbia University, the Boston Public Library, the second iteration of Madison Square Garden, the National Museum of American History and renovations of the White House among its myriad credits. Woodlea was completed in the mid-1890s, with some reporting the cost at $2.5 million (roughly $86 million today).

Sadly, Shepard did not live to see his masterpiece completed. In 1910, a decade and a half after his death, Shepard’s widow sold it to a group including William Rockefeller. The following year, Rockefeller and a band of corporate and political titans that included Cornelius Vanderbilt III, John Jacob Astor IV (who would die on the Titanic in 1912) and coal baron Edward Julius Berwind officially formed Sleepy Hollow Country Club.

The decision was made to transition Woodlea from a home to a functioning clubhouse, entertainment space and lodge. Shortly afterward, Charles Blair Macdonald and his associate Seth Raynor were hired to build nine golf holes.

— New Recipe

Even if they’re some of the greatest cooks the world has ever known, it’s still possible to have too many of them in the kitchen. Such was the case at Sleepy Hollow. When Macdonald and Raynor were hired, they were still early in their trailblazing careers. They had completed the National Golf Links of America and Piping Rock but were still sharpening their visions of template holes.

They built nine holes at Sleepy Hollow in 1914. When some land was sold off the property in the 1920s, a local architect named Tom Winton salvaged what was left. In the late 1920s, the club tapped another architecture all-time great in A.W. Tillinghast to take the club to 27 holes. But instead of elevating the course to new heights, the combination resulted in something closer to milquetoast.

A stream of other architects, including Robert Trent Jones Sr., touched the course over the following decades, but the results were more of the same. The routing lacked cohesion; the recipe had been jumbled. Finally, in 2005, Gil Hanse and noted Macdonald historian George Bahto were brought in to give the course a singular identity. Hanse, Bahto and the club agreed that it should be in the style of Macdonald, the course’s original architect.

The ensuing work was nothing short of remarkable. Hanse and Bahto whipped up a modern spin on the classic, pulling out trees and moving just enough earth to further highlight templates like the reverse Redan at the par-3 seventh and the stunning punchbowl green on the par-4 15th. The highly praised green complexes at the first, third, 10th and iconic 16th are examples of Hanse and Bahto taking their inspiration from Macdonald and Raynor.

The course quickly shot up in nearly every ranking, and the membership decided to show it off. The club had hosted a PGA Tour Champions event from 1986 to 1993 that was won by Hall of Famers Bob Charles and Lee Trevino, but this time a USGA championship felt appropriate. In 2023, Sleepy Hollow hosted the U.S. Mid-Amateur Championship to rave reviews.

Today, the club is a potent blend of past and present, with the old-school clubhouse looking down on a course capable of hosting big-time events. It’s even produced its own PGA Tour player: Cameron Young, son of longtime head pro David Young, grew up playing Hanse and Bahto’s revived masterpiece.

— Greatest Set

Sleepy Hollow’s fairways are very likely the only ones in the world where  Chi Chi Rodriguez made birdies and Beyoncé galavanted in a wedding dress. Such is the attraction of the Woodlea clubhouse and the course’s Hudson River vistas: Hollywood has long been part of the cavalcade of golfers making the pilgrimage to suburban New York City. It’s no wonder that Bill Murray is a member.

Sleepy Hollow’s film credits could fill up an IMDB page, with the clubhouse and grounds providing the backdrop for a series of movies, television shows and commercials. Hugh Jackman’s 2017 box-office hit The Greatest Showman filmed several scenes there, as did the 2010 romantic comedy The Bounty Hunter with Jennifer Aniston and Gerard Butler.

Television shows have lined up to shoot episodes in and around the clubhouse, including 30 Rock, The Good Wife, Gotham, Madam Secretary, Pan Am, Younger, Bull, Quantico, Ray Donovan, Elementary and The Blacklist.

In 2011, Beyoncé used the golf course and one of the upstairs bedrooms of the clubhouse to shoot the wedding-themed music video for her feisty ode to an ex-lover, “Best Thing I Never Had.”

One notable exception: Sleepy Hollow. Tim Burton’s 1999 Academy Award–winning horror flick with Johnny Depp and Christina Ricci was mostly shot in England. That’s fine. Members know that new legends are born here seemingly with every tee time, camera-light flicker and misty evening, when they swear you can hear galloping in the distance. •