Playing the Myth at Sleepy Hollow

Golf has many courses that can invoke a specific feeling, but one country club in Scarborough, New York, feels distinctly like October.

The Legend of Sleepy Hollow and it's Headless Horseman lives in the valley. The trees close in, the river sits below, but up on the hill it is the Sleepy Hollow Country Club that holds your attention with a champion course that starts demanding choices on the first tee. 

Here touch beats swagger; angles and trajectories matter. 

The legend below 

Washington Irving set his legendary chase near the Old Dutch Church and a wooden bridge. While the original bridge span is gone, a rustic bridge in the cemetery creates the image everyone can recognize. Conjured from Revolutionary War stories about a fallen Hessian trooper and a valley full of superstition. Stand at the church and the bridge, then look up toward the hillside. Bridges and gullies appear again, and though this time, they’re safe inside a private club, it’s easy to slip into your imagination.

How the club came to be

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What now stands as the clubhouse, rose up in the 1890’s as a grand house of the ridge called Woodlea. The estate changed hands in 1910, and Sleepy Hollow Country Club, with a board filled with early American titans of industry, was organized by the next year. C. B. Macdonald and Seth Raynor laid the course foundation and by 1930, A. W. Tillinghast had expanded to 27 holes. 

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Since 2005, the country club in Sleepy Hollow has been in it’s modern era. Efforts from Gil Hanse and George Bahto have brought back classic strategy and clean lines allowing the club to boast a championship 18 plus a 9 hole par 31 with firm targets and bold greens that reward a players’ planning.

The hillside in play

The course sits on a ridge with fairways that fall toward the Hudson, then climb back into the property. Players will cross small valleys on timber bridges. Wind can shift in those gaps, so it’s important to pick a start line and commit. Tees are on level pads. Greens are often raised or tucked, with defined tiers and edges. The pattern is clear: wide landing areas that ask for a specific angle, then precise approaches into firm targets.

Play for how the ball reacts on the ground. Use the high side to feed into position. Landing on the wrong tier leaves long, defensive putts.

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A few holes to circle

Hole 16: “Short.”
Wedge over a ravine to a square shouldered green ringed by bunkers. A shallow dip in the middle affects putts. Hit the correct tier. Pin high on the wrong shelf brings three putt into play.

Hole 18: “Mansion Rise.”
Uphill finisher toward the clubhouse. Favor the side of the fairway that opens the approach. The green sits up with a false front. Commit to the number or you will be chipping.

Short par 4 on the front.
Take position over length. Bunkers guard the aggressive line. A placed iron that leaves a full look at the green is the birdie play.

Par 5 with river exposure.
The second shot tempts a carry. The smarter score often comes from a layup to the safe third of the fairway that opens the angle into the green.

The bridge to No. 16 green

How to make a number

Choose a side on the tee. Most holes reward the half of the fairway that unlocks the green. Work backward from the hole location and let that decide the line.

Use height and run on purpose. Fall turf plays firm. A low runner that rides a shoulder or a spinner that dies into a shelf can be the right answer.

Pick a window in the wind. The valley swirls. Set your eyes on a window above the green, match the start line, and finish the swing. Commitment beats extra club.

Lag like it matters. Plateaus and squared edges make two putts a skill. Read speed first and take the simple leave.

Light fades across the river, the last putt drops, and you came for the legend but leave talking about angles, spin, and pace.

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Up on the hill it is lines and lies, rewards players for planning, rather than power. 
Down into the valley, it is the church and bridge where once, planning could have staved off legend.
Whether chasing a score or the lore, at Sleepy Hollow Country Club, you’ve got a rare opportunity to do both.