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The above map only shows the settlements the PCs would be vaguely aware of. This time, I stocked the map using a combination of methods. First, I used my old standby the Welsh Piper's Hex Based Campaign Design system. I decided that the major settlements would all be cities while minor settlements will all be towns instead of villages. I got one major settlement (which was obviously going to be Greyhawk) and two minor ones. I determined their populations using the system in the Greyhawk folio.
Now I wanted to determine where the farmland was. It seemed like it would be difficult to wed the Hex Based Campaign Design system with the Welsh Piper's equally excellent Medieval Demographics tool. Instead, I decided to use Rob Conley's figures for use with the Wilderlands. Since his numbers were largely based on Judges Guild material, I figured they'd be a better fit for a more fantastic setting like Greyhawk. I figured out the number of 5 mile hexes needed to feed the populations of each of the above settlements. Then I just placed that many hexes of farmland around each settlement.
Now, the overly meticulous regular readers may think to themselves "but Evan, wouldn't the hexes on this map be 6 miles, not 5?" Right you are! However, I'm lazy and I figured it was better to skew high and assume that the people of Greyhawk, Wizard's Bridge, and Blackleg sold the excess or used it to feed the men stationed at Portsmouth Castle.
This method is not precise by any means, but it makes slightly more sense than just having an isolated settlement with no farmland whatsoever. It also allows me to maintain a certain amount of wildness to the setting, which I enjoy.