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1.
A Place in upper westchester thats off the hizzle foshizzle. Them Straight up thugs of o-town chill down in sing sing and on spring street where you betta bring your sawn off.
Damn this town is ghetto. I must be in ossining
by fhurek May 31, 2004
 
2.
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
 
3.
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
 
4.
A town in upper Westchester.
Currently infested with creatures know as "wanksters"
Ossining pwns Briarcliff
by imnoteric March 01, 2008
 
5.
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 23, 2008
 
6.
A town full of faggots and only wish they were as cool as the kids from Sleepy Hollow High School.
Ossining Kid: We swallow hollow.
Sleepy Kid: Wow you're really gay.
by Wanna go five? January 24, 2009