Around here trail riding is fairly easy if you have a sensible trained horse. I’d have to haul an hour to hit rugged terrain. Having sensible riding companions is the most important part IME. I remember giving the boarders I was riding with in the early spring on the dirt road (because the ring was not usable yet due to a huge snowdrift that was still melting and we were legging up the horses that had months off) that in no uncertain terms that taking off for a brisk canter was NOT a good idea. We all lived, but it could have been too exciting.
I hope this makes sense! It’s been a long day.