Hey Runninghead,
Actually, I really like your style of mountains! They look very eroded, which lends your map a very authentic feel. I wouldn't change it if I were you, but because you asked, I'll be happy to share my method.
I do all of my mapping work in Photoshop, simply because I tend to work in all sorts of places: in the train, on a desk, in the sofa, ... I'm quite short on time so I try to use every minute I have. To get work done in a setting as mobile as possible, I purchased a second hand Microsoft Surface Pro 3 - the touch option and the excellent pen are just magnificent.
When it comes to drawing my mountains, I usually work in 4 steps.
- First of all I draw the outline of each of the mountains. Thin lines at the ends, and fat near the peak
- Then I connect them with ridge lines
- Then I add a first set of smaller ridges going all the way to the ground (thinning them as I go)
- And I finish it all off with a whole flurry of thinner lines suggesting shape and volume.
mountain_1.jpgmountain_2.jpgmountain_3.jpgmountain_4.jpg
Repeat these steps a gazillion times and you end up with a mountain range
What you might do to start suggesting shading right away is draw slightly thinner lines on one side of each mountain, lending them the impression they are lighted by an as-yet invisible light source.