Cristians,
I would slow down a sec here. Unless you really want to plow and till up that entire section of trail, maybe just take a step back. Can you wait one more year to accept a perfectly smooth trail through here? Just keep mowing it, and it will be grassy soon.
If you have trees and bushes over 1" in diameter, you really ought to get the roots out in the first step. I like to clear trail by pushing the saplings and bushes over, often pulling the roots/stumps out with them, and then use my tooth bar on my loader bucket to pluck the rootballs out if necessary. If you brush-hog right through the 2-3" diameter stuff, then you should really just wait for it to die after repeated mowings. Otherwise you're talking about completely plowing up this length of trail.