Inside the epic clubhouse of Sleepy Hollow, one of golf’s most luxurious resorts
Golfers, ghosts, and the Gilded Age. This story involves these three people.
At its center is Sleepy Hollow Country Club in New York’s Hudson Valley, home to a top 100 course in the world and a one-of-a-kind clubhouse.
The course was designed by CB Macdonald and Seth Raynor (with significant contributions from AW Tillinghast), while the clubhouse is attributed to the firm of Stanford White, a towering figure in late 19th century architecture who also designed the famous clubhouse at Shinnecock Hills.
The Sleepy Hollow project was originally intended to be a residence—a 140-room mansion for Maggie Vanderbilt, heiress to her family’s railroad and shipping fortune. But Maggie didn’t think of it as a home. The Vanderbilt family sold the estate to a group of early club members, who transformed it into a stunningly ornate clubhouse that complements the artistry of the course itself.
The clubhouse overlooks the Hudson River and offers stunning panoramic views. While it is a monument to the Gilded Age, it also draws on deeper local lore. The club’s name and its ethos are indelibly linked to Washington Irving’s “The Legend of Sleepy Hollow,” a ghost story set on the roadside. Statues of the Headless Horseman guard the men’s locker room, and the Ghost Rider has long been a widely recognized symbol of the club (in one version of the logo, the Headless Horseman holds a flaming pumpkin; in another, he holds a severed head; guess which one is the most sold in the pro shop?).
The grandeur of “Sleepy Hollow” attracts members to participate. Among them was the Rockefeller family, who purchased land across the river to ensure the view from the clubhouse was unspoiled.
The details inside are equally eye-catching: soaring, sumptuous plaster ceilings; ornately carved columns, fireplaces and bookcases: exquisite craftsmanship embodying an era when decoration was a virtue and no expense was spared. Even the surrounding gardens have a distinguished pedigree—they were designed by the children of Frederick Law Olmsted, the visionary behind Central Park. The clubhouse has 18 ornately decorated rooms, one of which is said to be haunted. That’s the risk when your history is ingrained.
Earlier this fall, GOLF.com took a look at an intimate tour of Sleepy Hollow and created a video (Watch in the player above) showcases the clubhouse and its surroundings in all their glory, including stables, clay pigeon shooting facilities, outdoor amphitheater and more. You can even get a glimpse of the on-site home where local hero and Ryder Cup star Cameron Young grew up. That’s a nice perk for a kid whose father is the club’s long-time head professional.
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