the richest town in Northern Westchester. Home to JAPs, jews, and maybe 2 black families. The public schools are more like private schools and the houses are bigger than the apartment buildings in NYC. The high school parking lot has nicer cars than all of the facility put together. Little 4-year-old girls are wearing designer clothes from head to toe, let alone high schoolers. All of the guys customize their shoes and buy new pairs every week. Summers are spent at camp and in the hamptons, winters in Aspen and the caribbian. In the 7th and 8th Grade Bar/Bat Mitzvahs take up all of the weekends with more than 150 to go to. Most often than not, only the father works and he brings in more money to take care of 50 other families in the town. All through high school, there are many parties attended where all the kids get wasted and are high. Every girl falls for every guy and is a total whore and slut. No parent cares what their child is doing on a friday and saturday nights, even if they are drinking and getting high. Chappaqua is the most spoiled town in Northern Westchester.
by AMAZZZZINGgggggg1234 January 10, 2009
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A town in upper Westchester, similar to Scarsdale, but for the more elite and less nouveau-riche. Formerly more popular among the privately wealthy before names like Larry David, Jeff van Gundy, and of course, the Clintons came to town.
"We looked at houses in Scarsdale, but it's just too jejune for our tastes. I moved to Chappaqua instead."
by Chadwick Bradford Simmons, IV November 28, 2004
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nice place filled with nice people living quiet woodland's life. Also known as the ghetto of Westchester.
Tommy: I here derrick is from chappaqua
Paul: Aw, that's nice, I bet he likes the woods
Tommy: Yup.
by akon and MJ January 12, 2011
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A place that people apparently don't like because I read the other definitions and they made me cry because I live there and even though it is mostly true, it does not apply to everyone who lives there.
I live in Chappaqua and everyone is mean to me except for my friends and I only have 6, but the schools are nice.
by wafewaffle January 17, 2012
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a quaint town in northern Westchester that is set in a generally woodsy area. citizens enjoy the simple life in their leisurely neighbourhoods, doing nothing but relaxing with their perfect families and tending to their gardens.
Person A: Hello. I currently reside in Chappaqua.
Person B: As do I. Can you help me tend to my garden? Rumour has it yours is marvelous.
Person A: Most certainly. I have a lot of time on my hands.
by geniesrus July 05, 2012
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the worst town in the whole entire world. never go to it. its too rich, too bitchy, too jewish, and too smart. the schools are all too good and too hard. the boys are too ugly. and everyone thinks theyre the shit. when theyre not. if you dont shop at nordstrom or bloomingdales or wear lacoste chappaqua is not for you. most people thnk theyre black. when infact, they are the farthest from black. reality is starting to hit most though. we have the clintonsbut who cares. life revolves around one single person. if its not you, get used to it. in chappaqua, no one has friends. chances are, all of your friends hate you. and you probably hate them too. everyone knows everything about everyone. johnny and sue hooked up. OH MY GOD JOHNNY AND SUE HAD SEX AND NOW SUE IS PREGNANT. only in chappaqua.
"yeah she owns NINE lacoste shirts SIX juicy outfits and TWELVE pairs of solows."
"at the party last night jane gave bill head so now u BETTER not talk to her"
by crazyg February 03, 2005
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A small town in Westchester, NY. 97% of this town is full of shit. The highschool kids get piss drunk and incredibly high every weekend because it's all they have to do. The cops always bust their faggot-ass parties. Almost everyone is Jewish and rich. Everyone talks about everyone behind each others' backs. Most of the girls are total sluts and a lot of the guys think they are "gangster". It is extremely rare to find a great guy or girl in Chappaqua, and if you do, it's probably because they didn't grow up there. At the highschool, Horace Greeley Highschool, the homecoming dance is a giant orgy and all the girls (who are pale, have bad skin, and dress like skanks) hook up with 6+ guys in one night. Most of the girls here are shallow dumbasses with nothing better to do than permanently straighten their hair and wear Abercrombie so they can stick their small asses out. Not to mention, the girls are also total bitches. Chappaqua used to be "okay" considering the fact that girls didn't used to be as slutty, and the parties consisted of more than drinking and hooking up with everyone, but now it's total shit. You don't make it very far in highschool as a girl if you're not fake and hot. The sophomores victimize you if you are a freshman girl and they always think they're better than everyone else. Everyone has a dying need to go to 6 different people's houses in one night because one party at one house is clearly not enough. On AIM, most girls from this town taalkkk likeee thissss loll hahaaa. <33 lyl Freshman tend to get drunk every weekend too because they are puny little underclassmen that seek acceptance by partying and drinking. The parents of these obscene kids don't know how bad they are because they don't actually like their kids at all and don't give a damn about the fact that their "perfect little angels" are actually getting high and having sex all the time. Nearly everyone is fake, and if you end up living there I will pray for you.

Not all people from Chappaqua are like this. But MOST ARE. Beware. I live here, and can't stand how ridiculous this town is.

Girl from Chappaqua: Ohmmygoddd I hooked up with Dan lastt night I was likkee soo highh I don't even remember hahaaa. But I kind of want to hook up with Greg nowwww he's so hottt = <3

Girl from outside of Chappaqua: Wow. You are clearly from Chappaqua.
by whatsupsucker November 15, 2008
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