Spooky horse

Ponying him behind a steady, mature trail horse would most likely help him to overcome some of his fears of the trail. The more he sees of the world, the better.

Poncho (the big horse) has no issues with anything except water crossing. It's nice to have some ideas for when the doc gives me the ok to ride again
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Completely random but - Chickens! Having chooks in your horses yard and stable help them deal with sudden movement and behaivour. If you watch chooks, they naturally just run and jump wings flapping screeching whenever they please. Eventually the horses just give up on shying as they get used to it (plus the eggs are a bonus )

My neighbors have chickens and I'm always fighting to keep my idiot dog from eating them. Though fresh eggs would be nice
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Bahaha bet the dog would be happy too! The chickens work well for us, unless the horses see a kangaroo coming for them they are pretty good!
Also he may just feel a bit insecure, being young and all. So when his herd mate freaked, he did too. Horses will always choose to run, and they aren't thinking of your well being in the process.

FWIW, I just always assume my mare will either jump an invisible fence, or suddenly do the "OMG Crouch". I tend to use a bastardized forward seat, because that helps when Mia jumps the fence I cannot see. I always try to keep my legs kinda wrapped around her. If she is about to bolt forward, I'll pull hard to the left (usually - her good side) and we'll do a 180. If need be, we may do 3-4 180s. It is far less common now, but she'll never be a horse who strolls down a trail, a cigarette hanging from her mouth...

I sometimes wonder what it would be like to be relaxed on a horse. But unless I someday stuff Mia, I may never find out.

After having a horse who how should I put it.... engages you as an active member of the trail ride....the relaxed horses are kinda boring in comparison