I did this with my younger horse, who started from a more precarious place than your horse. He was anxious, spooky, and had managed to injure me several times. There was a time I would have sold him if I had thought he could be safely trial ridden by potential buyers. I would have laughed in astonished disbelief if anyone had told me our first ever, solo, off property trail ride would be a 25 mile endurance ride.
The solo bit was accidental and my horse was great. He didn’t want to cross the ditch with running water and I dismounted, stepped across and got out of his way as he jumped, then remounted. Horses passed him and he let them vanish. ahead without fuss.
Anyway I did a lot of handwalking trails. Often after I rode I would handwalk a little way down the trail, then did a very short loop. Then I rode out, dismounting if he ever got too anxious. I did some Warwick Schiller stuff with him to help him let go of his rabbits (anxiety).
I handwalked a ton last winter (19-20) and let him do whatever he wanted within the boundaries I set. His feet couldn’t go past mine (stop, back up, pause, walk on - got to the point of just swinging the whip round from my left side to in front on him and he’d slow down ). He couldn’t push into my space (stop, back up,. pause, walk on). He had to walk with me (if he stopped then when I got to the end of the lead rope he had to move). We’d do rabbit practice if he was spooking at something. Basically I let him worry, spook, get curious, touch things, walk his own pace, whatever as long as he was paying enough attention to me to stay out of my space and respond to anything I asked immediately. The early walks were probably 55% forward and 45% backwards.
Your biggest thing is your confidence. A little handwalk after a ride gets you out seeing how your horse feels about it. Then you ride the same path you walked, and at any point you can just dismount if you’re concerned about a reaction. Ride with purpose, not relaxed on a loose rein, and you will minimize spooks and maximize your chances of staying on any spooks.
I rode with others but I always got ready early so I could ride in the ring and see how my horse was that day, and get him settled and tuned in to me. Unfortunately the others tended to rush when they saw me go out and my 20min shrank to 10 which was often not enough and I sent them off without me. I would keep riding in the ring and sometimes could get out for a loop, sometimes not. I have also dismounted and walked back alone when another horse in the group was acting up and making my horse anxious. I was able to remount before getting all the way back.
Being willing to do what makes you comfortable is important. Remembering to tell your horse what you want them to do instead of just allowing them to do what the other horse is doing will keep your horse listening to you. When we trot in a group I let the rider in front trot away varying distances before I ask for trot so that my horse doesn’t just trot off when the other horse does. I didn’t let the distance get big enough for my horse to get anxious which allowed that distance to grow to the point he didn’t worry about being left behind by passing horses on the Endurance ride last year.
He can lead, follow (I don’t make him follow the pony for very long because his stride has to shorten too much for his comfort) and ride beside other horses. I usually go up front for cantering, though he is learning to canter in the middle of the group. He learned that just because the horse behind canters it doesn’t mean he should canter.
He’s really good most of the time now. I have no hesitation in jumping off and handwalking if I think it’s safer (like the day the snowmobile came along the trail behind us).
Forget other people’s expectations and decide your own.