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A. That would depend very much on your cat. If you have an outgoing cat who seems to take most things in stride, then you can certainly try it. But if you have a cat who hides under the bed at even the slightest change in routine, I wouldn’t recommend it.
Let’s assume you have a cat who’s a prospect for walking — or a kitten you can raise to accept a walk as part of his normal routine. Get the harness — a cat harness is a must, because a cat can slip out of one made for a dog — and introduce your cat to it very slowly, with lots of treats and praise. When you see that your cat is comfortable having the harness around, work up to short periods with it on — again, with treats and praise.
Walking a cat isn’t like walking a dog. While you train a dog to go where you go without pulling you off your feet — or you should do that, anyway — walking a cat is really about accompanying a cat while he wanders around. Try this in the house at first to get your cat used to having a leash on. When he seems fairly accepting of both harness and leash, graduate to exploring on leash in your own safe yard.
If all’s going well up to that point, it’s time to go for a real walk. Considering the damage a terrified cat can inflict on someone holding a leash (and offering a tree substitute to climb when in danger), you want to be sure any place you walk is unlikely to have dogs, especially loose ones. If there's a chance that your cat could come into contact with another cat on the walk, you'll want to make sure that your cat has been vaccinated properly — talk to your veterinarian about how to protect your cat from diseases that can be transmitted from other cats.
Really, you’re probably not going to engage in long nature hikes with your cat, so you’re talking about going a couple of lots in either direction from your front door. Otherwise, you’d have to get in the car, which presents an entirely different set of challenges, unless your cat is already comfortable with a carrier and a car ride.
I’m guessing by now you’ve realized why most cats don’t get walked. In fact, those harnesses and leashes are probably more often used as safety devices to prevent a cat from escaping when you’re going somewhere like the veterinarian’s. I have seen them on cats who are traveling by air as carry-on luggage with their owners. In such circumstances, having a cat wear a harness with you holding the leash is a very good idea just in case your cat gets loose.
Otherwise, it’s more than likely your cat will be just as happy if he never sees a harness, much less wears one. If all you're trying to accomplish is getting your indoor cat some access to the outside, that's probably better accomplished with a roomy cat patio.
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