St. George's is the oldest continuously inhabited town of English origin in the New World.  However, I think they lose points because they didn't MEAN for it to be; they did get ship wrecked, after all.  The town was founded in the early 1600's.  Annoyingly, I can't find an exact date, but I think it's somewhere around 1610 when a return voyage was made a few years after the Sea Venture was shipwrecked (See the main page).  It is named after both Sir George Somers(one of the founders) as well as the founding saint of England.

  The town itself is fairly small and compact and as it is said in some places, it hasn't changed much since the 1600's.  For instance, there isn't a single traffic light that I can think of.  Being the first town on the island, it was also the first capital(The capital today is Hamilton).  Visiting St. George's you wouldn't notice it though.  The only indication you get is the State House which is located on the King's Square.

  St. George's happens to be the place that I've stayed when visiting Bermuda.  Specifically, I've stayed at the St. George's Club(which is a time share).  You'll notice that I have much more information about St. George's than the rest of the island since most of my time has been spent there.  Personally, I also happen to like it the best.