A town in Westchester that everyone who lives there should be embarrassed to say they're from there. All the girls are bitchy and if you think you have friends you don't. You're friends from there most likely dont like you and will never keep in touch with them when you leave because you will leave, and gladly. All the guys are ugly and even if they aren't on the football team they still act like a classic football player in all those movies. The people who realize it's the worst place ever are desparate to move and try to wake up their friends and show them how terrible it is but if you haven't realized by high school, you won't ever realize and are a real JAP. Even the kids that are only half jewish or even a quarter tell their friends they're really only a little christian are really more jewish because they're so desparate to be jewish. Everyone has at least one coach thing, and numerous juicy outfits. No one is origional and think its strange when someone is origional. Everyone shops at the same stores and has the same clothes. This place is terrible, once I leave I am never ever going to come back and I am positive I won't ever miss it or the people here.

nice place filled with nice people living quiet woodland's life. Also known as the ghetto of Westchester.

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.

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.

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.

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.

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.

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.