Perhaps because of its northerly status, Portland often gets slighted as a destination. Really though, it's only a two hour drive from Boston (it's also accessible by the affordable Amtrak Downeaster train) and is well worth the scenic drive.
Portland is currently experiencing a resurgence, with a spruced-up waterfront enhanced by the historic buildings of the "Old Port" district, an excellent arts district (including the Portland Museum of Art - one of Maine's foremost museums) and best of all, a standout restaurant and brewpub scene.
Situated at the mouth of the Fore River, it's a lovely place to stroll around, with pretty harbor views on Commercial Street and atmospheric shopping and café options along Exchange Street.
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If you're hankering after a lobster roll, the nearby town of Cape Elizabeth is home to the fantastic Two Lights lobster shack. With some of the best scenery in all of Maine (lighthouse to the left, unruly ocean to the right), this low-key eatery gets top marks for its tasty seafood.