Nothing is more exciting than taking a day in mid-September to drive to Sleepy Hollow Country Club — a true treat, no trick, for golfers. Charles Blair MacDonald, one of the pioneers of methodical golf course engineering, designed the course. Prior to MacDonald, American courses were laid out in rudimentary fashion and mainly had nine holes. I imagine MacDonald, who studied in St. Andrews, Scotland, and was tutored in the game of golf by Old Tom Morris, was bound to become a golf course architect for the ages. MacDonald designed the first 18-hole course in the United States, The Chicago Club, and then moved to New York, where he created several masterpieces including the National Golf Links of America, which emulates the course architecture of Scotland and remains the home of the Walker Cup.

Sleepy Hollow was created in 1911 by some of the most prominent men of the time; the board consisted of individuals such as John Jacob Astor, Cornelius Vanderbilt, William Rockefeller and James Colgate. The course sits on 338 acres of the Washington Irving hills and woodlands adjacent to the Hudson River.

The club constantly ranks in the top 100 most prestigious country clubs in the United States. Beyond golf, it includes a riding facility with an indoor ring, two outdoor rings and 900 acres of Rockefeller trails. The club also features 10 clay tennis courts, a large swimming pool and a beautiful locker room, all adorned with the logo of Washington Irving’s headless horseman riding at full gallop with his head in his right hand.

We were the guests of the trade journal Business Travel News and Delta Air Lines on a beautiful day. Rain threatened, but it turned out to be a glorious afternoon. Thomas Civitano, vice president sales and marketing, Americas, Jumeirah Group; and Olivier Prévot, director, North America, Brussels Airlines, joined me. We enjoyed shots to the greens and laughs all day — never fearing The Legend of Sleepy Hollow!

Hole 1 | 417 yards, par 4 Sunnyside
After enjoying a nice luncheon in the beautiful clubhouse, we took to the first hole, which lies just below the mansion’s back doors. What should be a simple starting hole can be easily exacerbated by the tall pines lining the entire hole on the right. The temptation is to stay close to these pines, as the hole turns to the right toward the green, but many a drive gets caught in these branches, as Olivier and I did. Tom stayed far and clear, affording a clean shot to the green for an “easy” first-hole par.

Hole 10 | 172 yards, par 3 The Lake
Our team turned what should have been an easy hole into a horror as our poor caddy, Sam, watched in disbelief. Both Tom and Olivier stood over their balls from the tee with great anticipation, only to see their shots land near a rickety bridge to the right and in the water. Making sure I did not replicate their misfortune, I overshot the green, landing a few feet off the back. A simple chip also rolled well past the cup, as the green slopes from back to front, forcing our best ball to be a bogey.

Hole 10 © Francis X. Gallagher

Hole 11 | 433 yards, par 4 Ichabod’s Elbow
This is the top-ranked hole on the course, and it all comes down to the position of your drive. Ichabod’s Elbow will make you lose your head if you position the ball too far left or right. This dogleg right plays longer than the card indicates, and the second shot is to a slightly uphill green surrounded by four bunkers. Tom slammed a beautiful drive that landed squarely in the center, followed by an equally great hit by Olivier right center and myself left center. We were quite impressed with ourselves! But the green was difficult to hold, with approach shots landing over or short in various bunkered locations.

Hole 12 | 541 yards, par 5 Double Plateau
This challenging hole consists of a dogleg left with many obstacles to traverse, including a babbling brook. From the tee box, the safe shot is to hit your drive straight out, not trying to cut off too much of the corner of the dogleg. (If you did so, you could easily find yourself in trees, fescue or rocks.) The second shot makes you think of your best fairway strike: Can you clear the brook in the air, or is it best to place that wood back into the bag and lay up? Seldom do mid-handicappers like the three of us make the wise choice, and our second shots found Olivier way left over the water but deep in the fescue and Tom fishing for his ball. I barely cleared the water and could then approach the green with impunity for par.

Hole 16 | 155 yards, par 3 Panorama
Panorama does indeed offer beautiful, striking views of the Hudson River from the tee box — but in front of the view lies the green, which is square-shaped and surrounded by a contiguous beastly bunker. Falling into this trap is a fate I do not wish on any golfer. On the left side, a cute little bridge reminiscent of the Harry Potter books crosses over a small ravine of fescue, rock and other unpleasant features, where Tom found himself.

Hole 18 | 426 yards, par 4 Mansion Rise
The hole is aptly named, as the fairway climbs and climbs to a green that stands at the foot of the clubhouse and former home of Col. Eliot F. Shepard, husband of Cornelius Vanderbilt’s granddaughter, Margaret Vanderbilt. The absolutely beautiful clubhouse, worth a tour, bears historical significance.

From the tee box we were prepared for battle, knowing our balls would receive little roll, as gravity would work against us. I took a big swing and launched an incredible drive into the woods, hitting several trees and popping out back on the fairway to the laughs of my teammates. Tom and Olivier made clearer, precise connections, sending their balls in a double position “A” to attack the green. I knew it was impossible to reach the green in two, but my boys thought otherwise and lost sight of the advantage of accuracy. A beautiful and regal finishing hole that even Washington Irving would find poetic.

Sleepy Hollow Country Club

777 Albany Post Road
Scarborough, NY 10510-9245
tel 914 941 8070
sleepyhollowcc.org