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Medieval counties

Medieval counties

I have a continent already set up, and lore created. However, I don't want to have to go with the tedious process of creating the towns and villages that the PCs will encounter in the kingdom I've created. I went with the inside out approach of working with a detailed town and then create the areas around it, and so on.

My problem: I have five counties in the kingdom (still unnamed) that this starts in. Within those counties, there are smaller baronies. I would like help creating the terrain, cities, towns and other locations within this kingdom.
The map of the kingdom is attached.

Some basic information:
This kingdom is based off of Renaissance England. A renaissance of magic and the studies of it has only just started to make an impact on daily life, but centers of learning have been popping up.
The area around the road through the mountain range is already somewhat planned out. It is sparsely populated, mostly because it is essentially a buffer zone from the hordes that live in the swamps past the mountains. This is where the PCs are, since they are helping fight of an invasion of said tribes.
To the north of the kingdom is another kingdom (based of the norse). This kingdom is also invading (unknown if connected to the other invasion).
The kingdom is around 160,000 square miles (400x400)
Other areas should include: ports, mines, farms.
Dwarfs and gnomes live mostly around the mountain range, though they exist in other settlements.
Elves live in the forests, but they have a few settlements elsewhere as well as a large presence in the cities.
The races live in peace, and while the elven and dwarven kingdoms overlap the human ones, there are no border disputes. Since this is post-feudal, the elves and dwarves basically had autonomy.
Attached Images
File Type: png Kingdom.png (42.2 KB, 0 views)

drop the counties, your baronies cover those. Unless you want them to be smaller kingdoms within the kingdom.

This is indeed for the game I am running.
As for why counties over baronies: Historical accuracy. All a baron was was a lord, not necessarily even owning land. A count actually owned a considerable amount of land. And as I said, the world is coming out of a feudal society, so there is still a loose vassal system but it is starting to disintegrate.

If you wanna be historically accurate, there were many post-feudal societies around, as far back as 12th century. The population growth of europe was likely due to the existence of castles that were sprouting up (1000 AD and onwards is the 'high middle ages', because there was a lot of development before the black death came and whiped half the population out) and walled towns in which considerable economic growth could take place in order to support easier living (or at least, protection from attackers I suppose). Plots of lands were more than fiefs, but empires and kingdoms, suzerains and the idea of sovereignty (but actually I'll probably need to do more research on this).

Yeah, there were still fiefs in existence and the vassal system remained - probably up until the rennaissance, like you just stated. But great kingdoms and mighty armies existed long before then.

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