Jumping rope is a really fun trick to teach your pup, but you should be prepared to spend a fair amount of time working on it, as this is not an easy trick to teach your dog. It's a hard enough trick to teach a young dog, but it can be even harder for an old dog in some ways. However, since by now your dog should have mastered a few tricks such as 'jump' or 'jump up', which might make up for him being an older dog.
Before you start working on this trick, however, you should take your dog in to see his vet for a checkup. You want to make sure he is physically fit enough to take on the task. This way you won't have to worry about injuries during the training process.
While there is no way for your dog to hold his own jump rope, you can teach him to jump rope between two people and in time, if he is small enough, with one person. Jumping rope can be a lot of fun for everyone involved, it's a great trick to show off, and it's a great exercise. Bear in mind, you do need to be sure your pup is physically able to handle the rigors of training.
Although you can train with a helper, at first you may find you are better off tying one end of the jump rope to a stationary object such as a table, fence post, or tree. Also, worth noting is that the rope itself could become a distraction at first, but in time your dog will get used to it and being around it. Keep the training sessions short and above all, make them fun.
It really doesn't take much in the way of training supplies to teach jumping rope, and by now your dog has probably had the basic commands down pat for so long they are second nature to him. The act of jumping is natural to most dogs, all you are doing is training your dog to channel this natural talent into a fun activity that the whole family can enjoy.
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Beyond this, you need plenty of time and patience to train your older dog to jump rope. But as long as you are willing to put in the time, the end results are more than worth the effort.