As to the mountains, you'll have to hand-draw them. Start by drawing a ridge-line for the full mountain chain then add some offshoot ridge-lines but not too many. On a new layer shade the on either side of the line to create the slope. Last, go back and delete the layer with the ridge-line. Now this just applies to the particular old map that you showed. Most folks like to leave the ridge-line in and I believe that there are 2 or 3 tutorials for drawing like this but you'll have to poke around to be sure.