I don't know your horse's personality. I can only offer my experience with my horse. I got him at age 5 as an OTTB. He liked trail riding instantly but was quite reactive and always a follower. In the first year, we learned and perfected the one rein stop and never went out alone. He never once offered to lead.
Second year I had him, I started pushing his comfort zone a little. I would stay basically in sight of the barn, but take him out into fields to where I knew there would things that would make him spook. I'd ride him up to an object, use the one rein stop 80 zillion times until he figured out he wasn't going to be able to run away, and then just sat there until he relaxed. Depending on how much effort he put into trying to manage his fear and relaxing, I'd either take him past the object or turn him around and let him off the hook. Either way he was rewarded a lot for meeting me halfway. That same year, he started occasionally taking the lead when out on the trails for short periods of time. This told me he was getting confidence in both me and himself.
Year 3, (this year) we moved to a new barn. All sorts of new things to test, but I know how much I can push him and he knows what I'll put up with and what isn't allowed. We've become a good team. I took a few weeks to get him used to going further and further from his new barn, first just walking around the paddocks, then into the fields, and just recently our first solo trail ride into the woods. While he did hesitate a few times, he knew that the only solution is to go forward, so that's what he did. A few things that would have made him spook 2 years ago only created minor twitches instead. We only went about 10 minutes before coming back out, but I'm incredibly proud of the progress we've made together. He's clearly making an effort to manage his fear rather than try to run from it.
I guess my point is, learn how far you can push him and where his limits are. Be a leader and establish clear boundaries for him. If you don't know how to emergency stop him, learn it. It's the single best tool in my trail riding tool box. Whether you ride him for 5 minutes or 2 hours, don't stop until he relaxes even if it's for a moment. It might take years of going out with another horse before he's ready to tackle it alone, but be patient. Eventually he'll tell you one way or the other if it's in him. Good luck.
You just have to see your distance...you don't have to like it.