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I agree with the previous suggestions: if at all possible, get connected with someone at your barn or in a local saddle club who owns a seasoned trail horse and ask if they would be willing to ride with you from time to time, as a confidence-booster for your own horse.

Be clear about the fact that you are working on introducing your horse to trails, so you may need to do some training-breaks along the way if your horse starts having issues.

If you just say "hey, can I join you on a ride some time," they may not realize that this is more of a "training" ride. That can end up being frustrating for them and nerve-wrecking for you and your horse.

Happy trails!
 
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