And the answer is...

Its a map generated with Appendix B: Random Wilderness Generation (1E DMG p173).

While the generator seems to have been intended for use "in play" as the party moves from empty hex to empty hex, I was curious to see what a randomly generated map would look like. As an aside, if a section of this nature was included in OSRIC, I can't find it, or something like the Castle Tables in Appendix C, p.182-183. Maybe someone wants to put together an OSRIC appendix for this?

As Mr. Mishler somehow intuited (are you psychic?;) the original map was just the area detailed above, with Beckshire as its center. I used Beckshire as a "home base" several weeks back for an OSRIC one-off the day after the "One Page Dungeon" contest winners were released (goblin caves of some sort, very vicious, iirc). That same group (we usually play board games like Diplomacy or Risk) asked for a couple more sessions, and with the Wilderlands S&W game on hiatus I'm happy to oblige. With Beckshire's immediate environs penciled in, I followed with a rough coastal outline, a couple of major waterways, and then went to work with the random chart, one hex after another.

Since I usually use the Wilderlands setting, I wanted a map of similar scale and scope.

The map took maybe two hours to generate, drawing included, and I was pleasantly surprised with the results. I was expecting a hodgepodge of terrains (a lake, then a plain, then a mountain, then a swamp, etc), but things turned out to make a weird sort of sense. Mountain chains emerged, often with foothills, even a great forest.

Then it was time to go back over each hex, and check for "Inhabitation". With only a 16% chance of a result, I was predicting something of a barren Wilderness. What followed was, again, surprising...(to be continued)