As I'm writing this, I have a small hexmap in front of me. It's a 30x30 hexmap, with a 12-mile scale. So, grab one yourself. Generate a random one if you must.
Now, I believe you are familiar with the terms pointcrawl, pathcrawl and dungeon crawl. If not, click on the links I've provided. I'll wait.
Now generate a random dungeon. Any size will do, but use only 1 level (for now we won't need more than that).
But why do all this?
Let me explain. When you talk about a point/pathcrawl concept, you are saying the connections between important sites on your map are important--those connections are the corridors of your dungeon, and those sites are your rooms.--We'll merge this concept now.
So place your dungeon map over your wilderness hexmap. If you are using an image editor, you may use a multiply effect on the dungeon layer and lower the opacity a little. Now that's done you have a large dungeon over your wilderness.
Each room is now a site, an important landmark, a settlement, a lair, a ruin... Each corridor is now a path, a way to link those sites: roads, trails, landmark chains, river banks...
Then you will ask me: why this particular path goes north 20 miles and then returns south, just to link this two towns 5 miles apart? It's because:
-there's a ravine
-it's a route used by pilgrims and now it's considered good luck to follow it
-the contractor who built the route was earning his money based on the amount of paved miles
-all the above
Those little things give color to your world. Suddenly, a twisting path becomes part of the setting and all you needed was a dungeon map overlay. ;-)
PS: This also works if you use a Traveller Subsector Map Generator as an overlay.
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