Union Oyster House

41 Union Street

What it is: An oyster house that is the oldest restaurant in America

Why it's cool: Located along the Freedom Trail just one block from Faneuil Hall, this designated national historic landmark has been serving freshly shucked oysters since 1826. Take a seat at the fabled, semi-circular bar where Daniel Webster was known to throw back tall tumblers of brandy and six plates of oysters, or reserve the booth where John F. Kennedy loved to feast.