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I can tell you that it wasn't ever anything I thought about when I was younger. I rode my friends' horses all over the place, I rode livery horses. It wasn't until I bought Estes that Mom suggested I get liability insurance for her. She and Bill had to have liability insurance when we ran the livery, of course, but it never occurred to me to carry it on my own personal horse. But why didn't it? Mostly because I was the only one who rode her, and I have health insurance, so if I got hurt riding, my health insurance would cover any injuries I might have.
There are so many ways horses can cause injuries not only to yourself, but others. What if your horse got out of the pen and was hit by a car? Happened to a friend of mine. Her horse was killed and the car was totalled, but the people in the car were okay. What if they hadn't been okay? What if their car insurance didn't cover a horse/car accident? She would have been on the hook for damages.
Our horses live right next to the livery. People line up for their livery rides between the livery hitch rail and our fence. What's to stop them from allowing their children to climb into our fence with our horses? It's happened before. People can be clueless about the dangers of horses and often don't think twice about letting their children run amok.
Out on the trail, there are so many hazards that can cause accidents, not the least of which are other animals. Mom's arm got busted by someone else's horse. Thank God Mom carries good accident insurance, otherwise she and Bill might have been out a whole lot more money.
Liability insurance for your horse in Colorado is cheap. Cheap-cheap. Like, $50/year for $1,000,000 coverage for an individual membership through the Colorado Horse Council. Like, $95/year for a family membership. A Google search turns up a whole heap of equine liability insurance options, from adding it to your homeowner's insurance to buying into a policy like we do with the CHC.
If you don't have liability insurance for your horses, even if you are the only one who handles and rides your horse, you should think about it. There's no telling what can go wrong and no one wants to lose everything over an accident.