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Portland is a fun, old shipping city. And I use the term "city" lightly.
Really, the best place to get quaint New England is in what's called "Old Port." Here you can sit out on the deck of a restaurant, eat lobster, listen to live music and watch boats go by. This, of course is in the summer when everything is open and it is acceptable to sit outside in Maine. In fact, summer is the best time to visit because it doesn't even get sweltering hot that often.
There is great shopping in this
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