A long time ago I wrote stippler and put the source on my blog.
However, it was pretty user-hostile software and doesn't even build with
current versions of Linux without modification. That's why I'm gratified
to see StippleGen 2, free software (LGPLv2.1+) that performs a similar function
but with a nice-looking user interface. I haven't tried it myself, but
if you are interested in making this kind of art it surely warrants a look.