Sharply divided into North and South. The southern half of the county which is closer to the city is heavily population suburbs while the towns to the north are more rural. The "Southerners", like me, don't consider Northern Westchester to really be part of our county.
Somers and Peekskill aren't Westchester, they're in Upstate New York or the "hudson valley" or whatever you want to call it. And by the way, Lower Westchester is not part of the Hudson valley contrary to every travel guide known to man, the HV is somewhere upstate or something. Really, what do Yonkers and Poughkeepsie really have in common?
by Arnold January 23, 2004
According to Census 2000, Westchester county ranks no.12 (instead of no.3) out of the 3219 counties (or county equivalent) in per capita income.

Well, it is still pretty high.
by Kai October 19, 2003
Suburban tract of land where people identify a little too much with NYC, as they don't actually live there. Face it, no one in Manhattan cares if you lived in the Bronx until you were 3 years old and then moved to Serene Hills, NY or wherever.
Why didn't Bill just move to the Upper East Side? What the hell is up in Chappaquiddick that's so great?
by Johnny X. June 19, 2005
-The WASPiest place on earth. Yes some parts are diverse, buy my god its so WASPy. People are arrogant, rich, snotty and act like they're above everyone socially. They make tons of money, probably never give a cent to charity, may be cheap, and spoil their rotten children who will grow up to be just as bad as their parents and hateful. Kids are bitchy, spoiled and always want the best. Mabye I shouldnt think it is so bad, but its just the white people are assholes.

-I have to tell you, I thought Staten Island was bad, then i came to Westchester. It even puts Long island to shame, but even the people of LI are not as stuck up as these assholes.

-by the way i live in Brooklyn, a place much more diverse then westchester, and I frequently travel through its many ethnic neighborhoods. Thank god for Brooklyn and NYC, and thank god i only visit my relatives in Westchester, who are actually not my favorite people and only moved from Brooklyn because "city life" was to congested and "stressful"
Many waspy shitheads and guineas live in Westchester
by tyc12 June 15, 2007
Long Island without that whole civilization thing.
In a nutshell, the ominous beginnings of Upstate New York. If the English Countryside is your idea of paradise, but you don't want to go all the way, then this is the place for you.
Person #1:

Hello, I live in Scarsdale! That's in Westchester.... Are you impressed yet?

Person #2:

You do? My condolences...
It must be like living in suburban Washington. I mean, everything is colonial, and you have to commute through ghetto everyday. Again, my condolences...
by Ditafooka February 14, 2010
A NYC suburban county with a slight inferiority complex to Long Island.
Half of the people I know from LI have no clue where I live even though Westchester is 25 minutes from Nassau County.
by Will January 8, 2004
A county full of white preppy fags
Wow your from Westchester? What a fag.
by Libla September 15, 2017