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Winchester is a town in Massachusetts about 8 miles north of Boston. The kids who live in Winchester usually have very rich parents and therefore they can get away with anything. People from Winchester are actually more obnoxious than the richer towns surrounding it (Weston, Wellesley, etc...) and try to make it seem like they are much better. They like to brag about how close they live to Boston because they think it's cool. And when they are around people from out of town they often say "wicked" more than they usually would -which is never- just so that people will know their proximity to Boston.
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