Westchester is the county directly North of NYC. the bronx is right to the south. Basically, there are many different sections that are very different:

This list basically goes from S to N:

-Yonkers, Mt. Vernon, New Rochelle- These are the 3 biggest cities in Westchester, and are generally racially and financially diverse. The most gangsta of the county. Alot of chill people but getting worse with gangs. New Ros beast and has New Roc City. Im from Mt. Vernon- so its best. ANd yonkers is really big.

-Bronxville, Scarsdale, Eastchester, Crestwood,Pelham: Rich Southern Westchester towns. Extremely rich and snobby and pretty annoying. Kids either try to be ghetto or are proud of their wealth and wear kacki shorts and wear button down shirts, or like abercrombie and stuff like that.

-Greenburgh-Middle and Southern Westchester.
Greenburgh- Tarrytown, ELmsford, Hastings, Dobbs Ferry, Ardsley: Diverse, but separated by village. Tarrytowns and ELmsford are the coolest- diverse, some gangs and stuff, mainly cool kids. THen the Hudson towns other than Tarrytown are pretty rich and artsy but not really snobby.

-White Plains- Probably coolest part of Westchester. Malls, transportation center, diverse, something for everyone. Like a mini-Manhatten (45ish story buildings) Still cant compare to NYC though.

-Mt PLeasant- Surrounded by Greenburg White Plains and kinda Ossining. Contains Hawthorne Valhalla Sleepy Hollow Thornwood, andPleasantville. Basically the last good place. Its basically working and middleclass. Mix of whites and hispanics. Sleepy Hollow is very Hispanic, and has some well off areas, so does Pleasantville. Overall cool kids and some gangs. Hawthorne nd hollow are prob the best.

-Briarcliff and Chappaqua- Really rich and annoying. More preppy and spread out rich than Bronxville and stuff. Its kinda rurally suburba. Chappaqua is alot more annoying then Briarclffe. They both mad jewish and rich.

Then theres Ossining and Mt. Kisco. The 2 last cool towns. Mt. Kiscos becoming bigger and pretty diverse. Ossinings on the Hudson, and Mt. Kiscos got a lot of new stores and attractions. Ossining gets a lil annoying but overall good.

-Northern WC and Peekskill-
Peekskills the only last city in the county, and ill defend em by saying they aint upstate.
Westchester can be cool in some areas: MV, YO, NR, WP, GB, MP, OS

ANd wack in others: BxVl, Scrdl, rye
by Mike003 June 11, 2007

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A far superior version of Long Island.
by Anonymous July 29, 2003

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mostly suburban county bordering the bronx to the south and fairfield county, ct to the north. largely perceived as a haven for wealthy investment bankers, lawyers and doctors who commute to and work in manhattan, westchester does indeed have more than its fair share of elite golf courses (think winged foot), high-end stores (gucci, louis vuitton etc) and country clubs.

however, while one of the ten wealthiest counties in america, there is more to westchester than the popular public perception might suggest. herein lies a breakdown of westchester locales:

Preppy and Rich- think Rye, Bronxville and Larchmont. You'll find the old-school clubs (Larchmont Yacht, Westchester Country Club) and preppier atmospheres in these towns. Replete with pastel polos, sailboats and topsiders, these towns are among the wealthiest (if not necessarily flashiest) of the county.

Jappy and Rich- most famously Scarsdale and, to a lesser extent, Chappaqua. These towns are a bit more status-obsessed than their preppy counterparts. Their school systems are among the highest-performing in the nation and they tend to attract many Jewish and Asian families that put a premium on their children's educations. Think of designer clothes behind the wheel of a mercedes sports car as opposed to a vineyard vines polo behind the wheel of a jeeb or volvo to understand the difference between preppy and jappy wealth.

Guido Rich- Think Harrison, Pelham and parts of New Rochelle. Think gelled hair, Armani Exchange, fake tans and heavy make-up. Easy to confuse for imports from New Jersey.

Hollywood Rich- Much of the northern tier of the county, which is more rustic, appealing to celebrities seeking privacy. Bedford, North Salem, Pound Ridge and others boast several celebrity residents.

Ghetto- The last type of community one would associate with Westchester. Still, cities like Yonkers, Mount Vernon, (parts of) New Rochelle and Peekskille are far more socioeconomically and racially diverse than the rest of the county and make up a substantial portion of its population,
The classes of Westchester:

Bankers of English/Irish descent who live in Bronxville sail their boats out of Larchmont while their wives shop in Rye.

Bankers of Russian/Eastern European descent who live in Scarsdale and manage Bill Clinton's finances in Chappaqua with their Asian business partner.

"Waste Management Professionals" who live in $3 million homes and drive around Harrison in their souped-up Hummers.

Immigrant strivers in Yonkers, Mt. Vernon and Peekskille who, more often than not, tend to the lawns and house-cleaning needs of the three types mentioned above.
by Moder July 13, 2006

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West of philadelphia, a trendy first class party town home to west chester university of pennsylvania. A quaint historic village of thriving business, bars, and restaurants. A place where you can find anything youre looking for. Quality sports teams, GO RAMS! Kick ass bars, awesome parties, great food, and lovely women. Especially beautiful on those lovely fall days that drape the center of the city in shades of red, yellow and orange. West chester, I will always heart you.
West chester is the best small town in southeastern pennsylvania.
by Bak5580 July 28, 2006

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The county north of New York City, sometimes referred to as the "East Coast OC", this county boasts a strong history, culture, and an absurd amount of wealth. The southern half of the county is more suburban, while the northern half, while more rural, is certainly as affluent, and cannot be discounted. Yonkers is the largest city in the county, and is currently making a huge economical comeback, though it is still plagued by issues with the school district. Westchester is home to many celebrities and some of the best public schools in the country. Whether one hails from Scarsdale or Somers, they are Westchester-ites---and ultimately, Westchester is one of the most intriguing parts of the state and country to look at from a sociological and cultural standpoint.

Home of DMX, Mary J. Blige, the Clintons, Mike Myers, Richard Gere, Rob Thomas, the Reeves, Vanessa Williams, Susan Sarandon and Tim Robbins, among others.

Ella Fitzgerald was born in Yonkers, and a statue of her still stands in her old neighborhood. Matt Dillon grew up in New Rochelle and Mamoroneck. Dave Matthews briefly lived in Yorktown and attended YHS. The Son of Sam hailed from Yonkers, and Mariah Carey's house burned down in Westchester. Martha Stewart was confined to her home after prison in Bedford, and Calvin Klein owns a thoroughbred breeding farm in Somers.

Mahopac is NOT Westchester, and you can tell as soon as you step foot across the county line.
westchester is the best chester!
by tipsymcstagger June 29, 2006

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The area of New York immediately north of the Bronx. Has rich areas and poorer areas. Many kids from Westchester pretend to be ghetto while their parents make 6 figure salaries. Also, people from Southern Westchester (like myself) take much offense when told we are from "upstate".
Westchester County can be very boring.
by WC Native March 01, 2006

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a very nice, suburban country north of new york city. it contains the very rich, and moderatly poor. most of it is rich, white , preppy people who belong to a country club, and take day trips to the city with their friends.
did you see that girl with her collar popped
yeahhh shes from westchester -- so hot
by megan April 07, 2005

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A colloquialism for Westchester County, the county immediately north of New York City. Stereotyped as being rich, though this is not true to the extent that most people believe. Considered to be a counterpart to 'Long Island' i.e. Nassau and Suffolk Counties.
I live in Eastchester. That's in Westchester. hilarious
by Eastchester September 02, 2004

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