The Legend of Sleepy Hollow: A Spooky Story & Magical Golf Course

There’s part of the classic American short story, The Legend of Sleepy Hollow, where the iconic headless horseman is supernaturally barred from crossing a wooden bridge spanning a stream as he searches for, well, his missing head.

There are haunted bridges at Sleepy Hollow Country Club, too – built of rough-cut trees and timber in the 1820s style of when that story first came out – but don’t fret, they are easily crossable. And a magical design feature at one of the country’s most magical golf experiences.

At this time of year, the foliage around Sleepy Hollow Country Club is popping with reds, oranges, and yellows. It’s an idyllic fall golf experience, with a spooky Halloween-type feel to it, too.

The clubhouse was built in the late 1800s and features 18 hotel rooms. It was formerly a 140-room Vanderbilt mansion and, at one point, was one of the largest privately owned homes in the United States. Given it’s lengthy history – and the legend for which the club is named – it should come as no surprise to hear there are some unique characteristics to the place.

“Oh, I’ve heard people talk about that,” Director of Golf and PGA of America Golf Professional AJ Sikula says with a laugh of Sleepy Hollow’s spooky setup. “You go over the haunted bridge that takes you across the little valley from 16 tee to 16 green and from the third tee to the third green – the way the club has constructed that bridge, it has some haunted feel to it.”

Sleepy Hollow’s logo doesn’t shy away from the haunted history, either. The headless horseman design, however, may be one of the very best logos in golf in the world. About 20 years ago, a member made a few tweaks to it and Sikula says the logo is yet another fun part to the club’s uniqueness.

It’s not yet gotten old to see guests come into the pro shop, credit cards at the ready, to buy whatever they can that boasts the headless horseman visual.

“I had like 20 people reach out when I first got the job (as Director of Golf) and they were like, you know, ‘great job’ or ‘what a great place’ or ‘you’re going to love it.’ But specifically, the comments were like, ‘oh that’s the best logo in golf,’” says Sikula. “It is really cool that people do find enjoyment in it.”

Sikula, too, has very quickly found enjoyment in his new leadership role at Sleepy Hollow. After attending Marshall University on a baseball scholarship where he played pitcher and middle infield, Sikula stayed on at the West Virginia school to get his MBA. At 25 he decided to join the golf industry and spent his summers in New England and his winters in south Florida.

Sikula’s employment resume is chalk full of top-tier spots – The Country Club in Brookline, Seminole Golf Club and Augusta National, to name a few. He got his first head pro job in the mountains of North Carolina at Grandfather Golf and Country Club and admitted he cried his “eyes out” when he left there after five years for a new role at the Inverness Club in Ohio. He was there for about three-and-a-half years before the call of the northeast came again, with his wife being from Boston.

“I’m just finishing year two and I’ve loved every single second,” Sikula says. “I knew that the golf course was really good coming into it and […] I finally got a decent day at the end of March (after starting a few months prior) and I walked tee to green, the entire golf course, and I came back in and was like, holy cow – I knew this place was good. But it was really, really good.”

Two years ago Sleepy Hollow hired a new superintendent, Jonathan Heywood, away from the incredible Morris County Golf Club after a half-decade (and a multi-year stint at Winged Foot’s famed East Course, too) and Sikula said he hears it about 30 times a week (and twice already prior to a mid-day chat with PGA.com) that the course is in the best shape the members have ever seen it.

“The playability – that’s probably my favorite thing about old-school architecture. It’s all about options,” Sikula says. The club underwent some hefty work from Gil Hanse and Jim Wagner in 2008 – a major, long-term restoration of the original C.B. Macdonald architecture.

“Especially now that the turf is firm and fast, it lends itself to options and makes it so fun to play.”

As legend has it, the Sleepy Hollow Country Club and its surrounding area and its on-site clubhouse all boast extra layers of curious storytelling and background. Now, we’re splitting hairs, as the golf course is actually located in Briarcliff Manor (overlooking New York’s Hudson River) – just about three miles from the actual town of Sleepy Hollow.

But that shouldn’t take away from the legend of the club, the incredible logo, and the getting-better-all-the-time golf course.

“It just adds to the intrigue,” Sikula says, “and it’s all exceptional.”