It depends on your truck and trailer.
I wouldn't go in snow and mud(or wet grass) with a dually pickup and a trailer that sits low or long.
But would have no issue with a single rear wheel tired, four wheel drive pickup and a short gooseneck that sits up off the ground or a truck with a rack, like boots mentioned, on a sheep trail/cow track.
With a truck and rack you can pretty much get turned around anywhere a pickup can, but either you got to have a place to unload(ramp or embankment) or have horses that will jump in and out of one.
I DON'T LEAD 'EM AND FEED 'EM, I RIDE 'EM AND SLIDE 'EM.