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Machias: 200 miles NE of Portland; 310 miles NE of Boston

The term "Downeast" comes from the old sailing-ship days. Ships heading east had the prevailing winds behind them, making it an easy "downhill" run to the eastern ports. Heading the other way took more skill and determination. Today, very few tourists venture farther east on U.S. 1 than Ellsworth. Yet there's an authenticity here that's been lost in much of the rest of coastal Maine, and many longtime visitors say this is what Maine used to look like in the '40s and '50s.