Boston is a very, very complicated city, as Oscar said. For a place that is central to the development of American culture, it's geographically peripheral and remote -- I can't tell you how many New Yorkers I've met who have never been to Boston and don't see much of a reason ever to do so. There's some egotism but it's mostly of a provincial, defensive, and neurotic kind that you would never find in New York. Some multigenerational residents tend to believe that they live in the "Hub of the Universe" (the most arrogant moniker for a city I could imagine) but they're also extremely articulate in making their case.
I admire the fact that people seem to value education, especially the ability to speak, over just about anything else, including the ability to earn money. "Old money/old family" Massachusetts gets away with way too much -- e.g. the Kennedys -- but the flip side is that not many people kowtow to new millionaires. Rents are (unjustifiably) the second or third highest in America because the old money doesn't budge and it lives off gouging college students. Tradition and classicism rules the day, which explains the fact that the music is stuck in the '80s. Bostonians' wonderful way with words makes the bars really interesting. Union guys get into some cerebral discussions over a few pints, and then get up and brawl with Yankees fans. There's a definite sense of group identity out here which extends to class and race, as well as a lot of clubs based on random childhood obsessions like cupcakes and kickball. A fog of white-bread innocence covers most of New England.
As an outsider who will probably be living here for a long time due to a job, it can be hard to understand the complexity of the collective life, let alone break into it. The college students don't need to try -- they'll be leaving after four years so this is their time to enjoy each other rather than the city. I'm kicking myself for not having gone to college here -- during the school year, pretty college women are all over the streets and it feels like a nonstop party. Because the rate of violent crime out here is very low (much better than anything in California) you can usually feel safe walking the streets at night.
With so many of the streets originally being designed for horses or cows, driving is horrible; they're narrow and scary. Even after the biggest public works project in history, the city needs a lot more renovations, especially to the public transportation, which can be amazing (SF Muni could learn something from it) but can also feel like a false promise if you're waiting for the Green or Orange lines. The weather is pretty bad (June this year was four weeks of cloudy weather with barely any sun) but then again few places in the U.S. outside California have perfect weather, and it's actually on the moderate side compared to the wild swings you find in the Midwest.
In short, a complicated place.
