go for it as long as they stop! The sheltland I used to ride had no breaks, so when I galloped him out bareback I could only turn him and he would eventually stop. I also use to gallop out my 14h pony that absolutely loved to gallop. He was dead easy to stop though.i took him over a 2ft log out and did it better then in the feild :) I still ride out now and then bareback on my mare that can be scatty. I find it easier to stay on her bareback sometimes rather then with a saddle on :) i'm like you, I prefer hacking then schooling.