It's written with an eye to people who recently moved to a new place (and with the inevitable academic slant), but you'd be surprised how much you don't know about they city you've lived in for years. Often familiarity makes everything seem muddy and somehow inevitable--of course it's like this, it's always been that way. A closer look at the history of a neighborhood, the life of a subculture within the city, or the endless political catfight that keeps the city afloat will probably surprise you no matter how long you've lived there--and possibly give you a grip on the issues in time for the next election.
Image from: http://www.davidrumsey.com/maps492.html
1. Look as a map of the city, on google maps. Play with the street view. Find a public transit map. Know that while it will be very accurate, digital mapping has its weaknesses and even the all-mighty google will fail to show you everything perfectly. Also google the city's skyline, and look at the different images people have of the city. What do they think it's like? What's the general aesthetic, or the cliche?
2. Take a walk. A long one, through several blocks. Look at the buildings there and think about how they got to be that way--what style of architecture it is, what it tells you about the historical development of that neighborhood, whether it's residential or retail and why, what economic strata it's in, how long it's looked this way. Read the fliers posted on walls and streetlights and see what people in the area care about. Look at the graffiti.
3. When you're done, go look up the local neighborhood historical society, if there is one, and find out if you were right. Which houses were made in the 19th century? When did the park get put in? How long has the area been part of the city?
4. Scope out the coffee shops in your neighborhood. Notice what kind of people eat at which restaurants. Go to that place you never eat at and try and figure out why you haven't been before.
Image from: http://www.cynic.org.uk/holidays/nyc2002/
5. See the cliches, all of them, because there's a reason tourists do that, and actually read the historical displays next to them.
6. If this city is west of the first thirteen colonies, look up its plat map online (For example, Cook County i.e. Chicago). You might try and find a secondary source that explains the plat map too--the interesting part is in understanding the quirks of how the city was first laid out.
Westward expansion in the U.S. was highly regimented, contrary to popular belief. Land was divided up in grid patterns, often with the same exact rectangle set aside for the same purpose in many different cities. One of the earlier patterns in Ohio, for instance, always had the same numbered lot earmarked as a school. Land was sold in plats to private owners, who often later subdivided them for further profit. A lot about how the city later came to be shaped was dictated by these plat maps and by how their first owners decided to develop them.
Also, the insanity of many cities' street layouts can be explained by the fact that landowners could put in streets however they wanted--they didn't have to hook them up to everyone else's. It also helped that the grids were often laid down with scant regard for actual local topography, creating awkward patches and irregular corners where elevation, marsh, rivers, or other geographical features interfered.
Now, most eastern cities were just laid out ad hoc according to the needs of the colonists, but there are sometimes sites like Bostonography or archives of various universities that will still contain maps of all kinds of eastern cities in various stages and through various lenses throughout their history.
Image from: http://www.flickr.com/people/sarahhsia/
7. Pick a restaurant that serves a regional cuisine you rarely eat, and go to that neighborhood to eat it. For example, Chinatown, Divan, Little Italy, Germantown, whatever. Chicago is spoiled in this regard, but most cities have small ethnic enclaves like this--for instance the Ethiopian restaurants and stores in Washington D.C. Order something you don't recognize, or ask the waiter for a recommendation. Bonus points if you're entirely unsure how to eat it.
8. Look up the city government web page, and scan the constitution. Strong city council or strong mayor? Note that often the constitution's intent doesn't work out--in theory Chicago has a strong council and a weak mayor. In practice? Well.....yeah.
(Fun Chicago exercise--check the last names on political figures of the last century from ward captain up through state senator and see how many of the last names are the same. I have a haunting feeling this will be interesting for many other cities as well.)
8. Read the local paper. Where does the power lie politically, in the state legislature or the city government? The governor? Attorney general? A mayor or the majority party's leader? What issues is the city concerned about? Space? Garbage disposal? Crime? You won't get this from the government web page (well, maybe you will, but they can be hard to squeeze real meaning from if you don't already know a good bit about the city), but you will get this from newspapers, op eds, forums, and the comments section on articles. The Politics section of The Commercial Appeal is a good example for the city of Memphis. Like all papers, it has a slant, but the articles and comments beneath them still give a good snapshot of the city officials and citizens' relationship.
The example I gave was of a particularly mainstream local paper, but specialty papers--say for entertainment-only, or LGBTQ papers, or radical political papers--also have a lot to say, with more detail if less breadth.
Image from: http://www.flickr.com/people/swanksalot/
9. If there's a public transit system, pick a bus or train line and ride it from one end to another. If not, go for a long drive to nowhere in particular.
10. The census makes maps nowadays. The 2010 data is coming on a rolling basis, so more and more states are going to appear. In the meantime, these are based on samples from 2005-9. Or there's quick facts if you're not the visual type. Old census data can be interesting too, for the contrast it makes with the present (though I recognize people not inherently fascinated by history and demographic shifts might not want to wade through too much data. Still, having a quick glance can be enlightening if you want to know how the city's changed).
11. Your city, chances are, has a restaurant week, during which the swankiest places to eat in the city offer prix-fixe three course meals, that would normally cost a hundred dollars or more, for somewhere between twenty and thirty-five dollars. You might want to get a reservation in advance, but it will be well worth it. Most cities have a website or somewhere participating restaurants are listed, and it will give you a good idea of what food culture is like in the city. It will also be delicious without impoverishing you.
12. Go to museums. Not just the big natural history/art museum, though you should go to those too. Go to the Textile Museum, or the Audubon Museum, the Museum of Contemporary Photography, or the Fire Museum of Greater Chicago (I've never been to the latter, it's new, but only good can come of it). Little out-of-the-way places like that usually are dedicated to a local luminary, or manufacturing product, or are just about a subject that a small group of people in the area really cared about.
Image from: http://si.smugmug.com/gallery/1674201/1/121703751_wHHGg#121703751_wHHGg
13. Go drawing/painting/photographing in an area of the city. Don't let lack of artistic inclination stop you--it'll give you a new way of looking at where you are. While you're at it, look at other people's paintings/drawings/photos of the city. What does everyone's eyes seem drawn to?
14. While you're in an artsy mode, find the art galleries. Most cities have a district spotted with small, local art galleries. What's the scene like where you are? Bookstores are also often good for poetry readings, local authors giving talks, that kind of thing. Any universities/colleges nearby will also be full of odd little events, though inevitably they will be somewhat less local in character.
