Town shaping question? (WIP map and debate?)

[Chlodowech]

If you don't want to get a city that looks planned, try to get a rectangular, triangular or even irregular central square.

And to answer your second question: A town usually grows outwards first, along the main roads. Those main roads could be quite irregular, e.g. if they pass a valley or a river at a certain spot. Later, the town will grow inward, too; any free space available in the city centre will be used for house building, which results in building on former squares (example), in the centre of wide roads (which will result in two narrow lanes; example: this english town) or even against bigger buildings like churches. But the outer quarter will still provide much free space for gardens.

There's a good example for this in Germany: The medieval town of Duderstadt

And another thing about the city walls. Theirs size and shape should depend on who founded or owned the city. If it was a rich duke or even the king, think about large walls including also the outer quarters of the town, or even a double wall ( a low curtain wall in front of the actual city wall). If it's a less important city, maybe only the central part is surrounded by city walls, or even be a palisade and ditch, maybe combined with stone gatehouses. And if there's a castle, it should be part of the walls and not inside or outside of them (because when there's a castle, the owner usually owns the city, too, and then he'll include his castle in the city's defense line).

And if there are bigger buildings close the central square (especially churches), never place them with their main facade to that square; it looks very planned)