16
a boring, small town in northern westchester. it isn't your typical suburb, there are no sidewalks, and the only shop owners that know your name are the nail salon ladies and people in that wrap place.

the "cool" people are either the fake hipsters in "vintage" clothes or the annoying japs in steve madden boots and leggings.
parties consist of pregaming, hooking up with as many people as you can, and pretending to not remember anything the next morning. everyone smokes weed once in their life if you live in chappaqua, and everyone fakes being high/drunk too. no excuses.

also, if you're friends with older kids, you're automatically a complete tool. it's so incredibly cliquey and boring.

there is a tremendous amount of pressure to go to a good school. it's not the biggest deal in the world if you're going to yale, since half of your grade is going to cornell anyways. but if you're going somewhere that doesnt require above a 3.5 average and thousands of extra-curricular activites, you get strange looks from everyone.
Person: So, where are you from?
Me: Chappaqua.
Person: Oh, that's cool. So, what Ivy League are you going to?

Chap Jap: I totally got these new leggings yesterday!
Chap "Hipster": Ew, she's so annoying. Plus, that outfit would look so much cooler with these Urban Outfitter tights i have in every color at home.

Person: Want to pregame at my house before Stan's? Seriously, how much would parties here suck if we weren't totally wasted the whole time?

Girl 1: I hooked up with 3 people last night.
Girl 2: Well, I remember hooking up with 4, but apparently, from what Mary told me, I hooked up with like 17!
by chapploseryo March 30, 2009
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17
The general consensus is that this town is the most unnaturally sheltered environment one could ever reside in. Which is why its NOT smart to raise kids here despite popular belief. An aging and isolated hamlet in Northern Westchester, truly lacking in diversity and overall quality of life. The whole 'town' shuts down by the early evening. Although even before the town closes, there's a pitifully scarce amount of things to do still, and many of the towns inhabitants have attitudes, are rude, obnoxious, and pay unnecessarily high taxes for an overly competitive school system that's been steadily declining in nationwide ratings since 2003. Most young adults leave instinctively upon completing there high school education because the town has very little to offer to say the least. Living here is also very costly and unaffordable, and has a very dreary and depressing feel to it with its limited woodsy surroundings and hills. Neighboring towns like Pleasantville to the South, or Mount Kisco to the North are within 10 minute proximity and also have a thousand times more of a real world feel compared to the undesirable, sheltered, and conservative, town of Chappaqua.
"Johns parents insisted that Chappaqua would be a marvelous place to live and raise a family, until John was immersed into the sheltered and disappointing excuse for a town."

"I can't believe I pay such high taxes, this middle school is decrepit, looks like a castle, and smells like garbage."

"There's really nothing to do here is there, besides walk around, eat pizza, and be given loose change and pennies on Halloween instead of candy by local retailer Squires."

by Tony44u April 01, 2009
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18
The home of the JAPS. It is a wealthy town in Westchester, NY where almost every kid is spoiled. They typically have iPhones, lap tops, Apple watches and basically every single apple product. The girls have high end make up that is to be shown off at school everyday. Oh and you better be wearing adidas superstars and lululemon leggings or a rly nice pair of jeans. If ur bm sucked well then ur so does ur social standing. Parents are typically rich and let their kids do anything.
Wow Emma's bat mitzvah was this past weekend, it totally sucked. I'm so not gonna be her friend anymore, what a loser. And what's even worse is she's from Chappaqua, it's supposed to be a great party.
by mgbh March 01, 2017
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