There's a company in my area called AriaLink that offers WiFi services to largish areas. They have several versions/packages, for example they manage free WiFi services for businesses like coffee shops. They also do free WiFi services for entire downtown areas, usually paid for by the city or a chamber of commerce, or just an association of business, etc. They service apartment buildings in a plan where the property owners pay for a wired internet connection and then the residents get "free" WiFi service at home (as part of their rent). They're trying to get contracts with a few local high schools. They also have a few neighborhoods where they are offering residential paid for high speed internet via WiFi.
The get back to the point, anyone can use any of their "free" hot spots (coffee houses, downtown city districts, etc). Anyone who has a paid account (either WiFi or DSL) can get on any of their networks - so for example if you were a resident of an apartment building with their services, so you have a login ID you can get on any of their other apartment building or neighborhood wifi networks.
I don't live in a big city, or even near a particularly large one (Lansing, MI is close by and it's only a few hundred thousand people) and while I can't get a WiFi signal EVERYWHERE with them, I can use it in my small town downtown, East Lansing's downtown, plus a handful of neighborhoods and shops scattered around the general area. They also have service in other cities nearby (they service all of the Beaner's coffee shops, for example). Lots of it is free, and it's pretty cheap if you want access to everywhere they have signal.
Point being that WiFi is starting spread to a lot of areas, and while it'll likely never hit rural or even all suburban areas, it'll become fairly ubiquitous in the next couple years, I think. The Touch will certainly help drive that... I expect the Touch to become the single most popular/purchased WiFi enabled portable device (non-laptop) within the next year or so.