I actually know what it feels like now. I can really, truly enjoy trail riding, and it feels great.
I find arena work quite boring, unless I'm actually trying to teach a horse something and need peace, quiet, and a confined area. We don't have access to an arena at our place, anyways. A few years ago we had an old, broken down, tiny old pony gelding that would go anywhere without a pulse, but I was getting much too big for him, so we gave him to a family that could actually use him and I got my first riding horse.
The mare is a sweetheart. Willing, respectful, obedient, not spooky, incredibly sane, but for the first year she was half green and very hot, and I was nervous and scared of her, and it lead to some less than fun trail rides. She never did anything to hurt me, but she was far from a fun ride. Since then, I've actually learned how to ride and the mare is a dream to be around. I've trailered her around to big group rides (and a couple where she was the only horse there) all over the place and she has been a superstar at all of them. But last year's trail experiences have always made me wary of trying to ride away from our property. I know she can do it-before we got her, even, the trainer put quite a few miles of trail experience on her. It's not her at all-it's just this complex I have.
My new pony (second horse, lucky me ) has changed my entire perspective on trail riding. She is cheeky, headstrong, independent and couldn't care less about me, but she spent the first 15 years of her life trail riding, and that is what she does best. She is an amazingly fantastic trail horse, go anywhere, any speed, doesn't call for the other horses, has yet to have a big spook, and just is everything I ever dreamed of having. I know my mare is the exact same way and wouldn't do any of that stuff either, but with the pony, I am actually experiencing it. Already, I can feel my confidence skyrocketing. I am no longer tense or nervous. I can ride down the road without fear. I can go the places I wouldn't have dared before.
And now that I am on my way to fixing myself, I have a good feeling about the trail future of me and my first mare. She can and will willingly do it, I just need to have confidence in myself, and this pony is giving it to me.