Make a map based on an entry from the Domesday Book. The entries for places include things like the number of households, how much farmland, and whether they include any other (taxable) assets such as a mill, etc.

You could try to make the map as authentic/historic as possible or you might simply use the information as the basis for a map. Or anything in between.

Alternatively if anyone can think of any other primary sources similar to the Domesday Book to base this sort challenge on, feel free to suggest them!