So as well as the area map, I am also going to try working on the city map for the dnd game I am in now.
I have joined part way through, so the town/city has already grown somewhat and stands at a population of about 4,000.
The initial city started of with Oleg's Trading Post and has grown since then in a number of phases as follows (these are areas not solo buildings):
1. Olegs (Shop)
2. Housing and Smith
3. Temple to Tempus
4. Jail, Garrison, Monument
5. City Walls
6. Housing and Inn
7. Market and Housing
8. Library and Shrine to Oghma
Going to try and design the city to show the development in these phases rather than planned from the start
I'd probably draw basic sketches of the phases separately then and note positions of things like earlier defensive ditches as they'll influence the street plan and will be the origin of street names (ie: dyke street). Anyway, I look forward to seeing it!
Ok, each 'plot' on the map (note some of the buildings they have built cover more than 1 plot) is meant to support about 250 people. A quick google search suggests 250/acre is realistic for a medieval city, so we can use that as the basis, therefore each plot is about 1 acre, is about 200ft x 200ft. or in squares 40 x 40
The map I have for Olegs is 28 x 22 which makes it too small. On this basis, so I have my first decision, do I have various stalls set up against the outside wall of the old fort, or do I have it as a higher density plot?
After a bit of thought I like the idea of a walled in bazaar, and am happy with it building upwards to cover expansion, so I am going to leave it that size.
Ok, the smith district then goes around the main road into olegs, and gathers around that main route. The bigger houses can then back onto the wall itself or on a new path striking east (towards the first farmlands they settled).
Which gets us the city looking like this at phase 2