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In Massachusetts I really like Provincetown for it's flamboyant character, liberalism, awesome scenic location at the end of the Cape, walkable downtown, beaches and the fact that it's one of the few places on the East Coast where you can see whales from shore.
Also like Rockport on the North Shore for its rugged beauty, charming downtown, and coastline.
Norhampton and Gloucester are technically cities, but they're small and I love both places.