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Saturday, January 24, 2026

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



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

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

The course was designed by CB Macdonald and Seth Raynor (with significant contributions from AW Tillinghast), and the clubhouse is credited 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 mansion—a 140-room mansion built for Maggie Vanderbilt, heiress to the family’s railroad and shipping fortune. But Maggie did not take it as a home. The Vanderbilts sold the property to a group of early club members, who transformed it into a clubhouse of stunning opulence—a fitting complement to the art of the course itself.

Overlooking the Hudson River, the club offers a stunning panorama. And while it stands as a monument to the Golden Age, it is also based on a deeper local lore. The club’s name — and its spirit — are indelibly linked to Washington Irving’s “Legend of Sleepy Hollow,” the ghost story set at the end of the street. A headless horseman statue guards the men’s locker room, and the spectral horseman has long served as the club’s widely recognized logo (in one version of the logo, the horseman holds a flaming pumpkin; in another, he holds a severed head; guess which one is the biggest seller in the pro shop?).

The grandeur of Sleepy Hollow drew members to match. Among them were the Rockefellers, who bought land across the river to ensure that the view from the club remained intact.

Inside, the details are a little surprising: high, extravagant plaster ceilings; Ornately carved columns, fireplaces and credenzas: craftsmanship that speaks of an era when ornament was a virtue and no expense was spared. Even the surrounding gardens have a distinguished pedigree—they were laid out by the children of Frederick Law Olmsted, the visionary behind Central Park. Among the 18 plush-adorned guest rooms, one is said to be haunted. Such are the dangers when your story goes deep.

Earlier this fall, GOLF.com was treated to an intimate tour of Sleepy Hollow The resulting video (look at the player above) shows the club in all its glory, as well as its surroundings, including the stables, trap shooting facility, outdoor amphitheater and more. You’ll even get a glimpse of the country residence where local hero – and Ryder Cup star – Cameron Young got up A nice perk for a kid whose father was the club’s longtime head pro.

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