The Democratic Donkey (and Grant) on Boston's Freedom Trail
Boston is the only North American city in my top five - Montreal would probably be number 6 if the list were extended. For me, Boston has a lot of the good things about America and few of the bad things - it's a sports-obsessed, bustling city with staggeringly cold winters. It has a vaguely European feel, thanks to the colonial history and preserved buildings. The city embraces it's fractured history, and the excellent Freedom Trail links the locations where America first stood up to the British. It also has a statue of a donkey you can sit on.
Boston is a great place to explore the rest of New England, it has a distinctive college-town feel to it, and a cheerfully rattling tram system. There are wild eagles that hunt squirrels in the parks (or pah-ks as the locals call them), it's small enough to explore on foot, and it's the home of Dunkin Donuts and the Fenway Frank. But it's not all good - it can trade too much on the olde times, and the Cheers bars (there are two) are terrible. But these are minor things compared to the Big Dig - the idea of putting all Boston's city centre freeways underground may have been a good one, but the unending building and demolition work has ripped the heart out of the city and made walking almost unpleasant, which is a real shame.
