I don't get a lot of chances to tail up a hill here in the Midwest, but believe it or not, there are a few rides with a few hills that warrant it. I love getting the chance to do it! Just remember, DO NOT showsheen your horse's tail if you plan to use it as a tow rope! I was at the Midwest Mt Quest last year and had done that to cut down on cockleburrs, and I had to wrap his tail around my hand to keep a grip on it.