The total elevation difference for Winchester Trail is 1,421 feet, and that is about average. Now, this is roughly a 2-day walk, so make sure you've got all your overnight gear packed. Now this backpacking and hiking trail is pretty long, so don't forget to pack enough supplies. Winchester Trail is a one trailhead great outdoors hiking trail, so in and out is the way to walk it normally. With its 14.6 miles of walking distance; it's a long hiking trail. The hiking trail stays roughly within the same elevation zone the whole time, so you won’t have to worry about different climate zones along your walk. At parts of the year this region sees very little rain, so do check for current fire restrictions before you go if you plan to bring a stove or make a camp fire.