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This is something that I hope to do with my dog someday, but with my own horse.

Depending on your dog, you, and the horse, it's sort of possible that you could train this in a few sessions. However, that's pretty unlikely.

I know lots of people that have horses and dogs, and a few of them have put in the effort to train their dogs for this, but most of them don't bother. Not only do you need to have your dog under control (and a 6ft lead is definitely on the short side for this, IMHO), but you still need to be ready to handle anything unexpected that happens during your ride - whether that's your dog going crazy after something, your horse spooking, sudden cross traffic (made worse if the other people on the trail are inconsiderate), etc.

Another point, even if your dog adjusts great (which almost never happens for dogs that have never encountered a horse before), the horse you're with may not. Be fair to the horse you'll be riding, and keep their experience in mind.

Also keeping the horse's experience in mind, how much/what kind of riding experience do you have? That can make a big difference to how the horse responds to anything unfamiliar in their environment.

If you decide to pursue this (which does sound like a ton of fun, by the way), keep in mind that most places that "rent out" horses will probably not allow you to bring your dog along - likely for most of the reasons I listed above. :)
 

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Thanks all!

I agree that 6 feet sounds crazy short! And I'm also concerned about tangles if it's longer. The only reason I'm considering it is that the stable said they have tons of visitors who do this. They actually suggested this when I talked to them about leaving my dog in the cabin when I go out on horseback. It never would have occurred to me otherwise.

I can absolutely take him to a local stable to learn to be around horses. I was wondering if it's necessary to take a riding lesson with him on lead. The problem is that a riding instructor is trained to teach people how to ride - not how to lead a dog with a horse! All the articles I've found on this subject seem to be more about how to teach the horse to be comfortable around the dog, with no mention of training the dog.

By the way he is a German Shorthaired Pointer, not a shepherd.
Whoops, just saw this post, I don't know why I missed it before! How cool that the place you're planning to go suggested bringing your dog along! That also speaks well for the likelihood of the horses all being exposed and well-adjusted to having dogs along for a trail ride.

I would definitely start with as much exposure to horses with your GSP as possible, work on OB and loose leash walking while there's activity going on. If any of the horses at your local stable are okay with a dog, do try and take some lessons to get your dog used to it. (I would probably try to work with an 8ft lead.) As long as the learning process goes smoothly, I'd say it's definitely worth the try. (and if it goes not-so-well for the first trail ride on your vacation, then you at least still have the option of the cabin as a safe place for your dog to stay during the rest of the rides.)
 
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