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Portland is why most people know this county, and it punches far above its size. For a city of roughly 70,000, it has collected an absurd number of James Beard awards. The lobster, the oysters, and the breweries earn the reputation.
Casco Bay sits right off downtown, scattered with islands you reach by ferry. Portland Head Light, just south in Cape Elizabeth, is one of the most photographed lighthouses anywhere.
Freeport, a few miles north, is home to the original L.L.Bean. The flagship store has no locks on the doors and stays open around the clock.
About 36% of Cumberland County households heat with oil, based on the 2019 American Community Survey. Maine relies on heating oil more than almost any state, so it's worth shopping around before winter.