The legend of sleepy hollow rides on: a "laid-back" retreat for the Social Register crowd and their friends preserves tradition, historic buildings and grounds, and family-friendly programs.

General Manager William Nitschke, CCM, of the Sleepy Hollow Club in Scarborough, NY isn't one to lose his head, but if he were to do so he'd be in the right neighborhood. As anyone who has read the classic Washington Irving story (or seen one of several Disney versions) can tell you, Sleepy Hollow, the town from which the club takes its name, is home base for the Headless Horseman.

The Headless Horseman of Irving's story--who appears on the club's logo--was a practical joker of the first ilk. Irritated that the foppish schoolmaster Ichabod Crane had stolen his girl, the jilted suitor played a brutal prank that relied on the legend of a decapitated Hessian mercenary buried in the local cemetery. Pulling a cape over his pate on a Halloween night, he pursued the hapless Crane on horseback. Approaching a bridge that is now near the third hole of the club's 6,547-yard Upper Course, the prankster hurled the pumpkin he had tucked under his arm at Crane, who kept on riding off into history.

There are still horses at Sleepy Hollow, but they're now Sleepy Hollow Club Nitschke's headache. The 50-horse stable with indoor and outdoor riding rings was designed by the firm of legendary New York architect Stanford White, which also designed the clubhouse building as a commission for Margaret Louisa Shepard, a granddaughter of Cornelius Vanderbilt.

Margaret Louisa was married to Elliott Fitch Shepard, whose primary success in life came as a recruiter for the Union Army during the Civil War. Retiring from the military, he failed impressively at both law and banking.

"Crank of Cranks"

He opened a bank at Fifth Avenue and Forty-Second Street which he called "The Bank of Banks." This hubris prompted one of his fathers-in-law, William Henry Vanderbilt, to anonymously compose a bit of doggerel for the New York Times referring to Shepherd as "The Crank of Cranks."

William Henry Vanderbilt died in 1887, leaving his daughter Maggie $10 million--most of which her husband Elliott managed to run through by the time of his death in various business ventures, including the purchase of New York's Mail and Express newspaper. Another financially expensive undertaking was the purchase of a 600-acre Hudson River estate from Butler Wright. The New York architectural firm of McKim, Mead, and White was hired to design "Woodlea," a new 70,000 sq. ft. manor house that today serves as the Sleepy Hollow clubhouse.

Shepard died in 1893 in a bizarre accident while being examined for kidney disease. Widow Margaret finished the manor house project, hiring the sons of famed landscape architect Frederick Law Olmsted, designer of Central Park to design the grounds.

In 1910, the estate--on which Margaret Shepard had spent over $2 million--was sold to Frank Vanderlip and William Rockefeller for $165,000. The men had no plans to sell or live on the property. Instead they wanted to create a first-class country club. In 1911 the Sleepy Hollow Country Club was incorporated. The first board of directors included a Vanderbilt, a Rockefeller, a young Averill Harriman, and Jack Astor, who would later die on the Titanic.

To this day members of those families, as well as other Social Register names, appear on the membership roster of Sleepy Hollow. For example, philanthropist Laurance Rockefeller, who died July 12 of this year, was a longtime member.

The club bought the property from Vanderlip and Rockefeller for $350,000 (The pair had more than doubled their investment in two years if you're keeping track) in 1912. Charles Blair Macdonald, the course designer and winner of the first U.S. Open, designed the original course in 1911. A.W. Tillinghast later re-designed the course and expanded it to 27 holes in the '30s.

In the club's first days it took nine "yea" board votes to bring you into the club and only two "blackballs" to keep you out. There is no waiting list for Sleepy Hollow today, but don't sit up waiting for your application form to arrive in the mail. "Membership is by invitation only," Nitschke said. "If (the board) wants to loosen up the selection process, they'll do it."

Being that selective and keeping fees as an afterthought meant that the club operated at a loss from the beginning (Even in the '50s, overnight rooms were $5 and formal dances cost $10 per couple). For 18 blissful years after its founding, funding capital costs and operating losses was not an issue: members simply anted up. The club hit its heyday in the '20s, adding a manager's house, a skeet house, a squash house, an indoor riding ring, and a swimming pool. There was also an outdoor theater and a 16th-century Italian portal. The original Butler Wright house became the golf house.

A Crash and a Change in Direction

The stock market crash of 1929 ended that golden era. The founding families were able to withstand the financial disaster, but many members were not. Five-acre lots were sold from club property to raise cash. Woodlea was only used for special occasions and the club mainly operated from the golf house. This dip in the fortunes of the club continued through the end of World War II. But shifting the focus from ostentation to basics also served as a catalyst for cultural change. The club became transformed from a gentlemen's outpost to a family "home."

While the membership was elite, the tone of the club was one of familiarity and egalitarianism that belied its patrician roots. That direction continues into the present. "The culture of this club is not stuffy," GM Nitschke said. "Their mission or vision is simply an atmosphere of excellence. They want excellent sports facilities and a variety of activity--squash racquetball, tennis, shooting, golf. Families arrive in the morning and disperse then go back home together at night."

The club was certainly not known for capital improvement programs in the past, and when major projects did occur, they sometimes headed in questionable directions. In the '50s Woodlea was remodeled with interiors reflecting the aesthetic of that era rather than the architectural heritage of the building. In the '60s an even bigger misstep occurred. The Butler Wright home, which had been used as a golf house, was pulled down and replaced with a low-slung, '60s-aesthetic addition housing locker rooms, pro shop, and dining facilities. The new building was located on the site of the Italian gardens that had served as a transition from Woodlea to the Hudson. The view from the Hudson River side of Woodlea is of the building's rooftop HVAC units. A book on the influence of the Vanderbilts on Gilded Age architecture stated that the addition resembles, "nothing so much as a half-submerged suburban supermarket." A $3.9 million renovation in 2000 remedied this aesthetic faux pas.

Board on a Mission

Bill Nitschke has been charged with the difficult balancing act of undoing years of deferred maintenance issues while preserving the comfortable feel of the members' home away from home. "There was a lot of deferred capital spending, but now the board is on a mission," Nitschke said. "When you're doing renovation on an 1893 mansion, you cry and then you go buy marble. Every time we have a plumbing leak, the insurance companies cringe. They want to know, 'What mural got ruined, or what little statue got dropped on the floor now?'"

Unlike some of the other grand old houses in the upper Hudson area, Nifschke noted, "This is not a museum, this is a working club. it's nice as can be, but it's got to be functional. The guest rooms can have original antique furnishings, but they'd better have working air conditioning and DVD players."

Today Sleepy Hollow has 20 guest rooms and 18 staff rooms, a ballroom, meeting rooms, a formal dining room, bar, grill dining, two golf courses, indoor and outdoor riding arenas, eight tennis courts, three squash courts, four paddle tennis courts, a swimming pool, a skeet and trap shooting facility, two member cottages, a library, and four staff housing facilities. The riding facilities back up to the Rockefeller Preserve, where members are permitted to ride through the 1,100 acres of woodlands, meadows, and wetlands that the Rockefeller family began deeding to the State of New York in 1983.

Which brings us back to the horses: "Horses are hell," Nitschke said. "I took on the challenge of a club that has a riding program and that's the reason I don't have any hair left." Nitschke does get some help with the hayburners from his members, including cash contributions to make improvements in the facilities.

Horses may demand a lot of attention, but maintaining consistent levels of service for humans is no mean trick. To serve its 573 members in all classes the club employs a staff of 60 permanent and 100-125 seasonal employees. That's a ratio one employee for every 2.2 members. Annual revenues are approximately $9 million. "We have a true melting pot of employees, representing 18 countries. The members treat our staff exceptionally well," Nitschke said. In 2002 the Club hosted the U.S. Women's Amateur Championship. It is included on John Sibbald Associates' "Platinum Club" list of the top 100 U.S. private country clubs.

These days you can still see names that harken back to the Gilded Age on the greens and tennis courts and in the dining rooms at Sleepy Hollow. Nitschke still remembers how daunting it was to have a member of the Rockefeller clan facing him during the job interview process. But after he was hired, he realized that they were also fantastic club members.

And if the members at Sleepy Hollow think you're good people, they just might ask you to join. Founders Frank Vanderlip and William Rockefeller and their cronies might have raised their eyebrows at the sight of comedian Bill Murray, a member of the club, who was the runner-up in this year's member/guest golf tournament. Murray plays in the colorful golf attire for which he is somewhat notorious. But Murray also caddied for a player during the U.S. Women's Amateur Championship in 2002. When the player's luggage went missing, Murray told her to buy whatever needed int he Sleepy Hollow pro shop.

The Headless Horseman would feel right at home.