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Sleepy Hollow Country Club is a private country club located in Scarborough-on-Hudson, New York. It was founded in 1911 by a group of local businessmen who wanted to create a golf course and social club in the area. The club has since expanded to include tennis courts, a swimming pool, a clubhouse, and several dining options. Sleepy Hollow Country Club is a prestigious institution that has hosted many notable members over the years, including business leaders, politicians, and celebrities.

Sleepy Hollow Country Club History and Founding

Sleepy Hollow Country Club was founded in 1911 by a group of local businessmen who were looking to create a golf course and social club in the Scarborough-on-Hudson area of New York. The club’s name was inspired by Washington Irving’s famous story “The Legend of Sleepy Hollow”, which was set in the nearby village of Sleepy Hollow.

The original golf course at Sleepy Hollow was designed by John Duncan Dunn, a well-known golf course architect of the time. However, in 1914, the club hired legendary golf course architect Charles Blair Macdonald to redesign the course. Macdonald, who had previously designed the National Golf Links of America in Southampton, New York, was known for his innovative and challenging course designs. His redesign of the Sleepy Hollow course included several signature holes, including the famous “Short” 4th hole, which requires a shot over a ravine to reach the green.

Sleepy Hollow Country Club quickly gained a reputation as one of the premier golf clubs in the country. In the years that followed, the club hosted numerous national championships, including the 1916 U.S. Open, which was won by Chick Evans. Other notable winners of championships held at Sleepy Hollow include Gene Sarazen, Walter Hagen, and Bobby Jones.

Over the years, Sleepy Hollow Country Club has expanded to include a variety of other amenities, including tennis courts, a swimming pool, and several dining options. The club remains a prestigious institution with a rich history and a commitment to excellence in golf and other activities.

Sleepy Hollow Country Club Membership Costs and Dues

As a private country club, Sleepy Hollow Country Club does not publicly disclose its membership costs and dues. However, it is generally understood that joining the club requires a substantial initiation fee, which is estimated can range from $10,000 to $100,000 depending on the type of membership and the current market conditions.

In addition to the initiation fee, members are typically required to pay rumored annual dues which can range from $5,000 to $50,000, which cover the cost of operating and maintaining the club’s facilities and amenities. The exact amount of annual dues can also vary depending on the type of membership and other factors.

Sleepy Hollow Country Club Amenities

Sleepy Hollow Country Club offers a range of amenities to its members, including:

Championship Golf Course: Sleepy Hollow’s golf course is one of the most highly regarded in the country, designed by renowned architect Charles Blair Macdonald. The course features challenging terrain, scenic views, and several signature holes, including the famous “Short” 4th hole.
Tennis Courts: The country club has several outdoor tennis courts, as well as an indoor tennis facility for year-round play. Members can take lessons, participate in clinics and tournaments, and enjoy social tennis events.
Swimming Pool: The club’s outdoor swimming pool is open during the summer months and offers a relaxing and refreshing escape from the heat. There is also a poolside cafe for snacks and refreshments.
Fitness Center: Sleepy Hollow’s fitness center is equipped with state-of-the-art equipment and offers a range of classes and personal training options.
Dining: The club features several dining options, including the award-winning restaurant, “The 28 Club”, which offers fine dining in an elegant setting. There is also a casual grill room and a bar for more casual dining and socializing.
Events and Activities: Sleepy Hollow hosts a range of events and activities throughout the year, including holiday parties, live music, and family-friendly events. There are also several social clubs and groups for members to join, including a book club, wine club, and men’s and women’s golf associations.

Overall, Sleepy Hollow Country Club offers a range of amenities and services for its members, catering to a variety of interests and preferences.

Sleepy Hollow Country Club Event Information and Dining Options

Sleepy Hollow Country Club is known for hosting a variety of events throughout the year for its members. Some of the events that take place at the club include holiday parties, live music performances, charity events, and golf tournaments. Members can also participate in social clubs and groups, such as the wine club, book club, and men’s and women’s golf associations.

In terms of dining options, Sleepy Hollow Country Club offers several options for its members. The 28 Club is the club’s main dining room and offers a fine dining experience in an elegant setting. The restaurant features a seasonal menu that highlights local ingredients and has received accolades for its cuisine and wine selection.

For more casual dining, members can visit the grill room or bar. The grill room offers a more relaxed atmosphere, with a menu that includes sandwiches, salads, and another casual fare. The bar serves up a variety of drinks and cocktails and is a popular spot for members to socialize.

Sleepy Hollow Country Club also offers catering services for members who are hosting private events or parties at the club. The catering team can create custom menus and provide event planning assistance to ensure that every detail is taken care of.

Overall, Sleepy Hollow Country Club offers a range of dining options and event services for its members, catering to a variety of tastes and preferences.

Sleepy Hollow Country Club Dress Code and Guest Policy

As a private country club, Sleepy Hollow has a dress code that all members and guests are expected to follow. The dress code varies depending on the area of the club and the time of day, but in general, the club requires a neat and appropriate appearance at all times.

For men, collared shirts and slacks are required on the golf course and in the clubhouse. Shorts may be worn on the golf course, but they must be Bermuda-length and tailored. Denim, cargo shorts, and athletic wear are not allowed on the golf course or in the clubhouse.

For women, appropriate golf attire is required on the course, including collared shirts and tailored shorts or slacks. Dresses and skirts are also allowed, but they must be of an appropriate length. In the clubhouse, women are expected to wear similar attire to men, including collared shirts, slacks, and dresses or skirts.

The club also has a guest policy that allows members to bring guests to the club. However, guests must be accompanied by a member at all times and must adhere to the club’s dress code and rules. Members are responsible for ensuring that their guests are aware of the club’s policies and act accordingly.

Overall, Sleepy Hollow Country Club has a strict dress code and guest policy to maintain a certain level of decorum and respect for the club and its members.

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