Reckon there will be a better person to answer this than lil o me. But I wanted to ask. Are you using a sharp stick with the ole wet n dirty stuff or a digital tablet ?
There was a tutorial by Delgondantelius which was fab and all about using inks and so on for mapping and specifically covered trees. So you can do an advanced search on that if I dont beat you to it and edit that link in.
Edit -- [Award Winner] Tutorial & Guide for Hand Drawn Maps (Pen & Ink w/ Photoshop)



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'say aragorn whats this green smudge?' 'oh well i drew this map myself and thats where i thought mirkwood was,m yeah im a bit off but didnt want to redraw it'. and im not too good at draawing individural trees, i cant do them well enough so ive settled for a squiggle with lines coming out of teh bottom and with lines on the insidfe hinting at a canpoy. here is problem number 2 though, because one side was against the shaded side of a mountain i had to define the outline with darker pen and that looked strange so i did all of the outlines in pen. so now it has a realy bold outline and a light interior, guess its hard to imagine without a picture so ill try and get one up soon. but would you say it is a good idea to shade the wooded areas? thanks
