While hunting for something else I came across the GeoGuff website. Created by Steve Anderson.
He includes some information about each place, using a standard format for the pages, including the meaning of the place name and also details of the local Wetherspoons if relevant.
Here's the start of the entry for Oakham, for example:
There are some useful images and lots of pub-quiz type facts and observations in each entry.
Why not see whether Simon has visited somewhere you know, or think about what you would include for a place that you visit over the coming summer holidays.