[Campaign Design] Looking for resources, examples and maps of small regions

I'm starting a new D&D 5E campaign in a little over a week and I'm trying to hammer down some details of the setting. Specifically, unless the PCs take off in a completely unexpected direction, the "first tier" is mainly going to be set in a small region that is about 300 square miles, or about 25 x 12 miles. I realized that I've never detailed a region this small and am looking for pointers, examples, maps, etc.

The gist of it is that it is one of several inhabited Havens within a larger frontier region. There are two towns, populations of around 900 and 700, and several small villages and farms, with a total population (mainly human) of around 7-8,000. Any examples of such regions out there? I suppose the Dales in the Forgotten Realms are the closest thing. Anything else? Any recommended resources? I've got tons of world building books, but am looking for something more specific to this sort of scale - or at least an example or two. Specifically I'm looking for ideas and examples of how to flesh out a small region in great detail. Anything from little locations to encounter ideas, etc.

Thanks!

There are a number of stuff right here at EN World:
http://www.enworld.org/forum/showthread.php?273046-Sapiento-s-Cartography-Area

There are more but you may have to search


The Cartographers Guild is another:
http://www.cartographersguild.com/forum.php

I am currently doing my own sandbox/hexcrawl campaign, with a hex map of 8x10 hexes with a diameter of 10 miles each - a bit larger than what you need, but I hope it might be useful. I am still filling out the details as the campaign progresses, but by now I have something for most of the hexes:



I've detailed the creation process in my blog - a list of the relevant blog posts can be found here, under the "Cold Frontier" section. I hope you will find it useful!