This is a one trailhead trail, so you're looking at an in and out backcountry trek. This is a long great outdoors hiking trail, so make sure you bring plenty of supplies. Now, this is roughly a 2-day walk, so better have big a backpack to fit all the stuff you need. The total elevation difference for Highline Trail is 2,264 feet which is an average number. Being 14 miles long; it's a long backcountry hiking trail. This backcountry hiking trail goes through some very different elevations which of course means you need to be prepared for different conditions on different parts of the backcountry hiking trail.