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When I moved to MA many years ago, I told someone at the office that I'd driven through Worcester - which, like a crazy person, I pronounced exactly the way it looks. Everyone fell over laughing at me, and explained that it was pronounced "Wooster" (for no apparent reason.)
A couple of months later I mentioned that I had to run an errand in Dorchester, and feeling better acclimated, I pronounced it "Dooster". And everyone fell over laughing at me again.


