Easton, founded in 1710, is both a quintessential Shore town and anything but. Its historic center, seemingly lifted from the pages of a children's book, is wedding-cake cute, locals are friendly and the antique shops and galleries are well stocked. That's because this isn't what Shore people would call a 'working water town,' which is to say, a town that relies on Bay seafood to live. Rather, Easton relies on the Bay for tourism purposes. It has retained the traditional appearance of a working water town by being a weekend retreat for folks from DC, Baltimore and further afield.
Ten miles southwest is Oxford, a small village with a history tracing to the 1600s and a fine spread of leafy streets and waterfront homes. Although you can drive there via US 333, it's well worth taking the old-fashioned ferry from Bellevue. At sunset there are memorable views.