A town on the Hudson River in Westchester County. It has 30,000 people. It has a train station, a few supermarkets, and McDonald's.

You have your drug-dealing ghetto that's like 70% Ecuadorian around Spring Street, the huge Jewish mansions in Waterview and Briarcliff, a lot of middle class people around 133, and a whole shitload of condos around St. Augustine's and 9A.

This makes the schools all awkward because you have the rich Abercrombie Jews in one part of the cafeteria, the fat redneck kids who hang out with the teachers talking about whichever New York football team is doing better, then you have the black kids who just do anything they want and don't care if they get suspended or go to summer school, and then you have the Ecuadorians. Ecuadorians make up like 30% of the school. All they do is talk with each other in Spanish, make out in the hallways, hang out at The Corner Deli, and playsoccer. Nobody really knows what goes on with the Ecuadorians.

In all, Ossining is an okay place to live. Just don't walk anywhere west of Route 9, cause you might get shot.
Michael: I live on Waterview Drive in Ossining. My house cost $800,000. I wear clothing from Abercrombie & Fitch every day.

DuShawn: Yo, I live in the ghetto part of O-Town, on Spring Street. Every day when I walk home from the high school, I pass ten drug dealers.

Gladys: Yo vivo en el calle State, en Ossining, Nueva York. Yo estoy Ecuatoriano. Veo el carcel de Sing Sing de mi casa. Yo tengo muchas amigas Ecuatorianas en la escuela.
by gomets729 December 14, 2010
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A town in Westchester County, New York, located 30 miles North of NYC on the Hudson River. Home of Sing Sing Prison.
I'm from Ossining...
by Michelle November 25, 2003
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A town in upper Westchester.
Currently infested with creatures know as "wanksters"
Ossining pwns Briarcliff
by imnoteric March 2, 2008
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Ossining is a shithole of a town in the lower halve of Westchester. the schools are full of shitty teachers ghetto lunch monitors and shit food. don't even get me started about the kids. the hallways are full of Ecuadorians that make out with each other nonmatter what gender or sex. the ghetto black kids that don't two shits about anything at all. then there are all the basic white girls with there high Nike socks and af1s. everybody in town thinks their in a gang and they all think they hard as fuck. Its a pretty ok town in general but if you live on spring street you definitely own a gun.
You live in Ossining?

You mean Ecuador.
by ossiningslander123 January 19, 2022
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A town made up of 70.26% whites, who pretend that they are not.
"Ossining is a town in Westchester County, New York, United States."
by Mythbusters February 24, 2008
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Ossining is a great little suburban town in Westchester NY. Ossining is a river town that sits on the Hudson. Spectacular sun set views and an easy 50 minute commute to NYC via the Hudson line make this a beautiful and easy place to live. Great diversity in the population and school district make this town a great place to raise smart socially aware kids.
I want to move to Ossining!
by Ossining mom March 11, 2019
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Ossining is a pussy town deep up in New York where they wanna be “hood” so bad they steal NYC slang and force a NY accent so they can “fit in” they even make up gangs that are also pussy and will get they will get they ass handed to em by anyone and everyone needless to say if you’re from Ossining your pussy Ossining heads stop tryna act ghetto and go ask daddy for his platinum card
Person one: he’s from Ossining
Person two: Ossining? Ossining hella pussy we on em
Person one: shit we out
by Ossining pussy February 27, 2020
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