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I lived in Portland, Maine for about 6 months this year and they have by far the greatest restaurants I've been to. Way better than NYC, where I lived for 8 years. Hotels in the Old Port is where you would want to be and it's probably cheap this time of year. Lots of bars and restaurants in a small walkable area. Some live music options also. The seafood of course is off the charts. Be sure to go to Street & Co for that, and The Grill Room is one of the best steakhouses I've been too.