Myth Drannor
Here is the main map:
The 32x32 overlay which has all the grid lines from the toolset:
The main map plus overlay:
The exact gridded map that I will use for the area:
First I lay down color for the roads and trees using the gridded map as a guide and going grid by grid. it is sort of a color by numbers game.
Then I spent a couple hours deciding the structure of Castle Cormanthor which you see in the center.
The next step was to terrain the area. With no topography map to reference I imagined the city would gently slope down torward the streams that divided it and the lake would be at the lowest point.
Here are contrasting maps to show the ruined areas:
I layed down red as a reference for where to build the ruined sections:
The city is divided into 4 neighborhoods. Canon tells us that each neighborhood has a unique color of marble curbs. The main thouroughfare is the Street of the Evening Star which has its own unique color - purple marble curbs. This is where the Street of the Evening Star passes the front gates of Castle Cormanthor.
Here I was deciding on general style of houses that would be used thruout the city. The focus will be on stone structures since wood structures would likely have deteriorated over 1000 years.
You can also see the possible choice of tree for the Shadowtops. That particular tree had a huge stable 300 feet above ground to house the city's flying mounts.