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13.
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
 
1.
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
 
2.
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
 
3.
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.
Chappaqua - AKA Jappaqua

by AMAZZZZINGgggggg1234 January 10, 2009
 
4.
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
 
5.
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
 
6.
Chappaqua may have some japs but it is an amazing place. Not many people are the way that everyone is describing them on this site. Most of the kids in high and middle school are weird, and don't even dress as well as people expect them to. There is only one popular group per grade, and there are only about 10 of them, and they are almost the only japs in the whole town. Nobody really wears anything designer in Chappaqua, I mean only the popular kids really do wear designer and it's not even real. It's just a bunch of knock-offs of juicy and tory burch. Plus, the education is amazing in Chappaqua. People have moved there just for the schools. In conclusion, Chappaqua really is a great place, and I don't really know why anyone wouldn't want to live here.
Hey, have you been to Chappaqua?

Ya! It's a great place. I was expecting it to be rich and jappy, but everyone was really nice and the houses weren't really big at all! I wanna move there now!
 
7.
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