I honestly don't remember when my first trail ride alone was. I was pretty young. I know that some people will probably think that my Dad was very irresponsible but I just have to share this story.
Every summer since 1990, we have had between 500 and 1200 head of yearling cattle kept on pasture for a feedlot. We are responsible for doctoring, counting, and making sure that they don't get out of the pastures. They arrive in the spring by trucks to a central corral area and then we separate them and drive them with horses and dogs to the pasture that they need to go to. Some of the pastures are more than 5 miles away from the corral. It was one of the first years, I was maybe 7. My dad separated about 75 head and told me to get my dogs. It had been raining all day and my hat was hanging down around my ears. He said to take these cattle to the Kellen place (which was about a mile and a half away from the corral). I took my 2 dogs and led the way down the dirt road to the pasture with the dogs bringing the cattle behind me. Went all the way down and all the way back by myself. He just had to go back later and close the gate. It could have been a disaster except he made sure that I always had the best horses and dogs that could do the job by themselves and all I had to do was point the way.
I always go trail riding by myself because that is when I have my "me" time with my horses. There have been several close calls and many times when I had to walk several miles back to the house but fortunately, I have never been seriously hurt when I was by myself.