The disc harrow is a great option. I have used many over the years, but mostly for field work.
There is actually two different questions here: How do I maintain a trail in the woods? And how do I maintain a meadow? Both deserve different attention and require different solutions.
I also live in the woods with trails and meadows. If you wish to maintain them with your tractor, you will need to prep the areas first.
What I did (and still do from time to time) on the trials:
Mow with rotary mower. Wider than you think you will need. Not by much, but if you are looking at a 5ft swath, then hug one side and overlap the other. I would say keep it out to 7ft. This way, overgrowth can creep in without choking the path. Remove all trees (+roots), rocks, stumps, mounds, etc before mowing. A box blade is handy for this, as well as an FEL. This is for future maintenance. Once this stuff is cleared, you can mow with confidence that there is nothing too horrible to damage your rotary mower in the future.
For the meadows, my first question would be what are you wanting to do with them? Are you looking to plant a food plot for wildlife? For you? Or do you just want to drive out to them to play with your tractor? I turned all of the natural clearings on my property into either ponds or food plots for deer and other wildlife. Here is what I did. I walked them and flagged the rocks, the stumps, and other debris. Then I mowed around those areas to be able to see better. Then I left the big rocks that I could not move, and removed the others. I then dug out the stumps down enough to cut them off and bury the rest of the roots. I removed the other debris (former owners left garbage, fence materials, and dead tires in these areas) to leave a cleared meadow. I then plowed some of the areas (mostly in the middle) and plated the different seed mixes for a wildlife food plot. I maintain these plots yearly, by doing some light mowing, and seed casting, maybe clean up a fallen tree. I also throw out salt licks and sometimes a hay bale for the deer to eat.
If you are looking to have a simple meadow, just wild grasses and shrubs, just let nature take care of it. No need to mow it or plow it. If you are needing/wanting to maintain the meadows, then you will need to clear or mark the areas that will damage equipment. Food plots (gardens) are a complete different animal. If your meadows are nothing but weeds and thistle, and you cannot have that (our county weed board has been hammering my neighbors) then you will need to take them to dirt and plant what you want. In any case, you will need to remove the rocks and other things that will damage equipment first. Hope this helps.