Overall, this is really excellent. My town is small but near Silicon Valley, and this does a great job of showing me stuff that's actually near me. Well done!

I imagine it's going to be hard to present information in the same way for large and small towns... Maybe you need some kind of a city/busy/crowded interface to give categories and narrow down, but for a little place without much of interest you just showed paged and ranked like this? Like, "entertainment in Chicago" or "food in Los Angeles" are way too broad a category to present in this format.