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If I understand correct, if it is an old trail, the trail is still there, you are just reclaiming it right?

You could pull debris back with the grapple onto an area of the trail you know is clean, then turn around and back over them with the cutter a few times to chop it up. It would take a while but little by little you will get through it. That does look pretty rough. Looks like kudzu or honeysuckle vines, maybe some wisteria (spelling?)
 
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