On a recent Wilderness pack trip we highlined at night and used a combination of hobbles, pickets, portable electric corral, and free roaming for foraging during the evening/morning.
At our first camp, two nights, I hobbled Big and let him go where he wanted. We had other horses in the corral and a couple tied up so I figured he wouldn't wander too far. He went about a quarter mile looking for grass. When I wanted to bring him in I just whistled and called and he nickered back at me and started in my direction. I walked out, clipped a lead rope on him, removed the hobbles, and led him back to the highline.
I took a risk letting him wander, even in hobbles. Knowing my horse it wasn't much of a risk--but he could have gone a very long way and gotten very, very, lost!
At our second camp one of the guys used a picket for his mustang. We had a big open field. The mustang broke free about 4 or 5 times. Then we quit using the picket.
One time when the mustang broke free he broke into the electric corral and managed to get all six horses stampeding in the field. Quite the little rodeo while we sorted it all out and got them all contained again! Biggest fear was them finding the trail and taking off down it toward the trailers about 5 or 6 miles away. Didn't happen, but could have been a problem.
In the future I think I'll hobble for foraging and run a short lead rope from the hobbles to the halter so he has to keep his head down. He won't go as far that way. And I'll highline at night as that seems to be the most safe and secure.
Beyond all that . . . First and foremost tip: find an experienced trail rider and go trail riding. Tell your eperienced partner that you're new to trail riding and would like all the tips and help he/she can give you. Me, I'm new to horses, let alone trail riding, and I've found a lot of people won't help you out for fear of offending you--so you gotta tell 'em you WANT their help and then thank them every time they provide it. Most people to teach greenhorns--but don't want to offend nor embarrass them so they might not volunteer to teach and will have to be asked.
Just my thoughts on it.
"Don't just feed it! Ride it!" And the People said "AMEN!"