A recent topic at the Holmes G+ community...
reminded me that I had created a document for my own use based on Erin Smale's essay on designing wilderness areas for D&D. I immediately recognized this as a very coherent version of the wilderness generation system in 0e, and later - from the DMG.
I added very little, except for a tiny bit of re-worded material from the DMG regarding setting up the terrain at the beginning, and castle inhabitants at the end. Erin's essay comprises the bulk of the material presented in the middle, the meat & potatoes, as it were.
However, there is an area of wilderness design that I've always thought should have been more developed was the random generation of waterways and roads. Easy enough, [woof] here it is, also towards the end.
With Erin's permission, I have posted the finished PDF here.