Gypsy, I started learning riding bitless as such, in a barn where beginners were not let to use bits. I did some research and came to a conclusion that it fits me, because I thought I'm not ready for riding a horse in a bit and for some time I also thought that bits are cruel - I've dropped that opinion since then, but I have no real experience riding with a bit, and I know and see a lot of experienced riders riding bitless with good results. Also, my horse had teeth problems up to very recent, so he showed great discomfort if I put a bit in his mouth, thus I'm now re-introducing him to the bit after a good floating.
About hackamores (I saw a question from somebody here about using them) - I ride either in a rope halter, either in a soft sidepull. I don't feel my horse needs the leverage, so I don't use a hackamore, but most of my barnmates use simple English hackamores and LG bridles. The rope halter is nice, but I find easier to learn proper contact and use of outer rein with a sidepull. But in trails I use my rope halter or sometimes just a cordeo, no headstall at all, and I haven't had any problems when encountering deer and moose - Snickers is quite a bold one when it comes to scary things. He'd rather investigate them than run from them.