I´ve bought a custom made side pull at a horse event some time ago. I decided to try it out in the riding ground, and it works well!
Riding bitless is really nice for both horse and rider. You don´t have to worry about not pulling the horse´s mouth and the horse relaxes a lot more. If your horse is all ready trained in the western technique, then it´s no problem how to manage it.
If you have an English style horse, you´ll might have to work at bit harder to make the horse turn it´s head. But maybe it will react naturally to it. You might do some training from the ground before riding.
I hope some day I’ll trust my horse enough to use it going trekking as well. But at the moment we’re still training on not running away from anything scary. There’s a LOT of scary things when we ride alone…
But the trust you build with your horse is all about being patient. I didn’t trust her this much in the riding ground only a month ago. First she needed time to settle down in the new place. Now she is calm enough for kids to ride her inside the fence!