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A country club in Scarborough New York where everyone is worth over a million. Everyone has at least two houses other than the one they live in. If youre "Cool" from the club you grew up there and cant remember anything from your childhood without someone or something from Sleepy Hollow in it. Everyone owns a horse and rides it either there or at another barn. The idea of vacationing is never anything short of a private yaht or a private plane. Skiing locally means out west and skiing far away is in Europe. If you don't play all of the sports offered there you are not considered an athlete. 90% of the moms there run in the new york marathon and the general rule is once you turn 50 you need to loose 50 lbs. It has the most milfs out of any club, most of which are trophy wives. The men golf on the nicest course in westchester, daily, then come in to the clubhouse have a bottle of scotch and a cigar and meet the family for dinner. An idea of a "bad day" on the golf course is 2 over par. Most sons can beat their fathers and like their fathers are playing college lacrosse or hockey. Anything short of a top 20 school is considered "a good, unrecognized school", most kids go to rehab before this.

Bill Murray can be sighted on the golf course on a regular basis, knowing that some members have more money than even he does.

Every kid wants to marry someone from Sleepy Hollow at Sleepy Hollow and its planned since theyre like 3.

The kids from sleepy hollow are brats, theres no way to deny it. When theyre told a rule they consistently break it and no one there likes the new management because they put rules in, which the kids dont listen to. The response to most things is "do you know who my father is" then the subject is dropped. The response to work is, hire someone. The kids here dont have to do anything for themselves because they know that they can always live off daddys money. A relaxing day is taking your boat out on the hudson with a drink and your mom while dads golfing.

People want to be them but once your on the inside you claim you hate it when you know that the country club will get you more places than college will. Everyone from there knows that people want to be them simply because they are that privledged, they are "the shit".
Mommy, Im going to play golf at the SLEEPY HOLLOW COUNTRY club today.

Dad, why is my boyfriend a better golfer than you?
by Mike HOCKEY11287 December 12, 2006
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