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1.
A small, high class town where sports are prominent. Cars like Mercedes Benz, BMW's and Corvettes are often seen prowling the streets. Known places of wealth are the Reserve, Forest Glen and Highland Falls. Also home to the OCC, (Orange County Choppers) So many choppers are seen as well. Near Newburgh, Cornwall and Cornwall on Hudson.
Person1: Hey where are you?
Person2: I'm visiting New Windsor!
Person1: Oh! Cool, Who'd you know there!?
by Torontoite March 25, 2011