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EXPLORE THE OLD PORT

Portland’s Old Port is aptly named, being old and located at the center of Portland’s active working harbor. The area lay in disuse until the 1970s, when a revival began. After you’ve taken a gander from the Portland Observatory (#5), head down Congress Street to explore the trendiest part of this vibrant little city.

You’ll walk past the Eastern Cemetery (the city’s oldest, dating from 1668), where noted Maine abolitionists and military heroes from several wars are buried. Stop and take a look at the Civil War Monument on the grave of Union volunteer Alonzo P. Stinson, who died at age 19 at the Battle of Bull Run, July 21, 1861. A granite bedroll sits atop the marker for the first Portland casualty of the Civil War.

When you hit India Street, you’ll see the first few of the many, many restaurants that crowd this section of the city harbor’s edge. India Street has Italian and Japanese restaurants.

Take a right off India onto Middle Street, where nearly every doorway is a restaurant—some with a national reputation and others that deserve to have one.

Head down to Commercial Street (on the water) and just keep walking until you find something that interests you, everything from speciality pizza, Irish fare, endless seafood-chowder-oyster-lobster