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I love Portland! Take a walk in the "Old Town" section of town with its cobblestone streets and sidewalks and some nice eclectic shops. We really enjoy Gritty McDuff's, a great brewpub with good microbrew beer and decent food. If you like hockey, Portland has an AHL team, the Pirates, there. There is a lighthouse not far from town, and if you like L.L. Bean, take a ride up to Freeport for their big store there as well as many other outlet shops. I'm sure you'll enjoy your visit!
Unfortunately, most if not all of the great lobster shacks/pounds will be closed during the time you're there. These are the places where you would fine the tastiest, freshest lobsters and lobster rolls for the best prices (think $6.99/lb for a 2lb whole lobster). You can of course get all the whole lobsters and lobster rolls you want from the diners and restaurants throughout the state, but you're be likely forced to pay premium prices for them.
But do NOT order the "McLobster" at McDonalds. I repeat and cannot stress enough, do not order this item. Better to go to just about any local place for lobster.
Did you post any of this on the Maine forum? They are pretty helpful there.
I got a good lobster roll at Foster's Clam Bake in York Harbor.
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