Nothing is more enjoyable than spending a mid-September day driving to Sleepy Hollow Country Club — a genuine treat for golfers. Designed by Charles Blair MacDonald, a pioneer of systematic golf course architecture, this course reflects a shift from the rudimentary nine-hole layouts that dominated early American golf. MacDonald, who studied the game in St. Andrews and learned from Old Tom Morris, became one of the country’s foremost course architects. He designed the first 18-hole course in the United States, The Chicago Club, then moved to New York and created several masterpieces, including the National Golf Links of America, which channels Scottish course design and remains associated with the Walker Cup.
Founded in 1911 by some of the era’s most prominent figures, Sleepy Hollow’s board originally included John Jacob Astor, Cornelius Vanderbilt, William Rockefeller and James Colgate. The course sprawls across 338 acres of the Washington Irving hills and woodlands near the Hudson River, offering both scenic beauty and classic design integrity.
The club consistently ranks among the top 100 private clubs in the United States. Beyond its outstanding golf, Sleepy Hollow offers an extensive riding facility with an indoor ring, two outdoor rings and extensive Rockefeller trails, plus 10 clay tennis courts, a large swimming pool and an elegant locker room. The club’s emblem — Washington Irving’s headless horseman galloping with his head in his right hand — decorates many of the facilities.
We enjoyed a sunny visit as guests of Business Travel News and Delta Air Lines. Rain was a possibility, but the day turned spectacular. Joining me were Thomas Civitano, vice president sales and marketing, Americas, Jumeirah Group, and Olivier Prévot, director, North America, Brussels Airlines. We spent the afternoon hitting greens and sharing laughs, never once fearing The Legend of Sleepy Hollow.
Hole 1 | 417 yards, par 4 — Sunnyside
After a pleasant lunch in the clubhouse, we started on the first hole just below the mansion’s back doors. What should play as a straightforward opener becomes tricky because of tall pines lining the right side. The hole doglegs right toward the green, tempting players to hug the trees, but drives can easily be caught in branches — as both Olivier and I discovered. Tom kept well left, avoided trouble, and had a clear approach to secure a routine first-hole par.
Hole 10 | 172 yards, par 3 — The Lake
What should have been an easy par turned chaotic for our group and especially for our caddy, Sam. Tom and Olivier both missed badly from the tee, their shots landing near a rickety bridge or splashing into the water. I overshot the green to avoid the same fate and then misread the slope, leaving a chip that rolled past the cup. The green’s back-to-front slope punished our best efforts and left us with a team bogey.
Hole 10 © Francis X. Gallagher
Hole 11 | 433 yards, par 4 — Ichabod’s Elbow
Often cited as the course’s signature hole, Ichabod’s Elbow hinges on drive placement. This dogleg right plays longer than the card suggests, and the uphill second shot demands precision into a green guarded by four bunkers. Tom hit a beautiful tee shot to the center, Olivier found the right-center and I landed left-center — all shots we felt good about. Yet the green proved tough to hold; approach shots frequently ended over or short in bunkered positions.
Hole 12 | 541 yards, par 5 — Double Plateau
This demanding dogleg left presents multiple hazards, including a brook that complicates the second shot. From the tee, the prudent play is a straight drive rather than trying to cut the corner and risk trees, fescue or rocks. The second shot forces a decision: carry the brook or lay up. As mid-handicappers, we often made the wrong choice. Olivier’s second landed deep in fescue left of the water, Tom searched for his ball, and I barely cleared the brook, leaving myself a chance to approach the green and save par.
Hole 16 | 155 yards, par 3 — Panorama
True to its name, Panorama offers sweeping views of the Hudson River from the tee. But the view comes with risk: the square green is encircled by a large, intimidating bunker. A little bridge on the left spans a small ravine filled with fescue, rock and other hazards — the area where Tom unfortunately found himself. The hole rewards a confident, precise iron and punishes anything short or sideways.
Hole 18 | 426 yards, par 4 — Mansion Rise
The finishing hole climbs up to a green at the foot of the historic clubhouse, once the home of Col. Eliot F. Shepard, husband of Margaret Vanderbilt. The fairway ascends steadily, and balls receive little roll as the incline works against distance. I launched an ambitious drive that ricocheted off trees and popped back onto the fairway, much to my partners’ amusement. Tom and Olivier hit more controlled drives, leaving tactical approaches to attack the green. It’s a noble, fitting finishing hole that echoes the club’s history and setting.
Sleepy Hollow Country Club
777 Albany Post Road
Scarborough, NY 10510-9245
tel 914 941 8070
sleepyhollowcc.org