Inside Sleepy Hollow’s epic clubhouse, one of golf’s most opulent retreats

Golfers, ghosts and the Gilded Age. This story involves all three.

At its center is Sleepy Hollow Country Club in New York’s Hudson Valley, home to a World Top 100 course and a clubhouse unlike any in the game.

The course was designed by C.B. Macdonald and Seth Raynor (with crucial contributions from A.W. Tillinghast), and the clubhouse is credited to the firm of Stanford White, a towering figure in late 19th-century architecture who also created the famous clubhouse at Shinnecock Hills.

The Sleepy Hollow project was originally meant to be a residence — a 140-room mansion built for Maggie Vanderbilt, heiress to the family’s railroad and shipping fortune. But Maggie didn’t take to it as a home. The Vanderbilts sold the estate to a group of early club members, who transformed it into a clubhouse of astounding opulence — a fitting complement to the artistry of the course itself.

Overlooking the Hudson River, the clubhouse offers a stunning panoramic. And while it stands as a monument to the Gilded Age, it also draws from a deeper local lore. The club’s name — and its spirit — are indelibly tied to Washington Irving’s “The Legend of Sleepy Hollow,” the ghost story set just down the road. A statue of the Headless Horseman guards the men’s locker room, and the spectral rider has long served as the club’s widely recognized logo (in one version of the logo, the horseman carries a flaming pumpkin; in another, he carries a severed head; guess which is the bigger seller in the pro shop?).

Sleepy Hollow’s grandeur attracted members to match. Among them were the Rockefellers, who purchased land across the river to ensure that the view from the clubhouse would remain unspoiled.

Inside, the details are every bit as striking: soaring, extravagant plaster ceilings; ornately carved columns, fireplaces and credenzas: craftsmanship that speaks to an era when ornament was a virtue, and no expense was spared. Even the surrounding gardens bear distinguished lineage — they were laid out by the children of Frederick Law Olmsted, the visionary behind Central Park. Among the clubhouse’s 18 plushly adorned guest rooms, one is said to be haunted. Such are the risks when your history runs deep.

Earlier this fall, GOLF.com was treated to an intimate tour of Sleepy Hollow The resulting video (watch in player above) showcases the clubhouse in all of its glory as well as its surrounds, including the stables, the trap-shooting facility, the outdoor amphitheater and more. You’ll even get a glimpse of the on-site residence where homegrown hero — and Ryder Cup star — Cameron Young was raised. A nice perk for a kid whose dad was the club’s longtime head pro.

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