During my recent brief sojourn into Massachusetts, I happened upon the Sheffield Covered Bridge, or Upper Sheffield Bridge, which crosses the Housatonic River in (yes, you guessed it) Sheffield.
It is closed to traffic and reminds me very much of the bridge between East Hampton and Colchester, except that less sunlight seeps in, which makes walking from one side to the other slightly frightening.
I have never defaced any sort of public or private property, but if I did, I would absolutely write "Lifes hard but u gotta suck it up & face the cold sick world show them ur better than them" and add some Stars of David. (I'd punctuate, though.)
Incidentally, the first English settler in what would later become Sheffield called it a "hideous howling wilderness." But I think it's rather nice.