It's hard to describe the correlation of music to the urban environment for me, but sometimes I hear something that, to my ears, sounds like a perfect "driving around town" tune, or a "driving into town on the expressway at night" song. "Radio Free Santa Fe," an FM station in Santa Fe that plays a lot of acoustic and hippie rock, is the perfect companion for lonely drives in the hills of northern New Mexico.
If anything, I envision a gritty 1970s Chicago whenever I hear old Chicago. However, I don't envision Boston when I hear Boston. I think of Tonawanda, a middle-class suburb of Buffalo, whenever I hear any mid-to-late 1960s pop "oldies." Tonawanda is a suburb that essentially popped up overnight; in 1950, it was mostly vacant farmland; in 1965 it was home to over 100,000 residents.
Whenever I see a new city, I often relate it to other cities. For instance, I think of St. Louis as "like Buffalo, times two, only all the buildings are brick, not frame."
Living outside of Orlando, I feel less of a connection to the place than when I lived in Denver, Las Cruces or Buffalo. Maybe that comes with time. Buffalo is home, and I care deeply about what happens there, even though I'm not living there anymore. Las Cruces, too ... for some reason, I have a lot of emotional energy invested in that place, and it also feels like "home," in a way. I feel at peace when I'm in Cruces, despite that city's glaring shortcomings. I liked Denver a lot, but for some reason it never felt like "home." Maybe because it was too clean, too vibrant, too prosperous ... it was an environment that was alien to me, having grown up in a declining city, and spending my first years in the "real world" in a booming yet poor region.
When I was looking to cash out of Denver, I desperately tried to get into the Kansas City region. It seemed like a good mix of Denver's prosperity and youth with Buffalo's honesty and grit; I felt very comfortable there whenever I visited. Unfortunately, KC wasn't in the cards.
I tend to prefer cities that are easy on the eyes ... clean, little or no billboard or sign clutter, nice landscaping.
