This story was told to us by my father who had more than one psychic experience. He did not like to speak about them often but told us this one which has always stuck with me.
Dad said that when he was a child, this would have been in the early 1950s, he would often visit friends after school. His family was poor and he would have to walk home afterwards. The area in which he lived is in one of the wildest parts of Monroe County, Indiana. There still is not much development out there and many of the roads are still gravel. I can only assume it was even more primitive back then.
One fall evening he had lost track of time and had stayed at a friend's house until dark. He knew he was going to be in trouble when he got home and was not eager to make the trip alone in the dark.
About half way home he was startled to see movement ahead. He was now at the bottom of a large hill looking at the top. On the summit, a rider on a black horse was crossing the road through the woods. He was wearing all black, a flowing cape and an old-fashioned tri-corner hat like the revolutionary war soldiers wore. Dad was frozen with fear wondering what the rider intended. The rider spurred his horse, which reared in the middle of the road, and the rider looked down at him and tipped his hat as if in greeting. The rider then crossed the road and continued off into the woods.
Dad said he ran the rest of the way home, still having to pass the spot where the rider appeared. There was something spectral about the whole deal which was confirmed when dad returned to the spot in broad daylight. He said he investigated the area. It was very thickly overgrown on both sides of the road. There was no way a real man and real horse passed through there that night. He never did find any explanation for these events. No one I have ever talked to has ever heard of a mysterious midnight rider lurking around these parts.