About me: My name is Rex Winterbottom. I've made a few orienteering maps.
Gather data such as LIDAR and aerial imagery, process the data, create a basemap in a CAD drawing tool such as OCAD or OpenOrienteeringMapper
Print aerial imagery, possibly with added data such as contours and trails or roads. Mark up the printer aerial photo while surveying the area with notes and symbols for drawing during the drafting process. It's also possible to do this with a tablet device or phone and draft while you field check.
Using your field notes, create objects on the map that represent the features in the terrain.