I have hiked the trails on Mt. Hood many times but I have never done Timberline Trail as a backpack. I thought I might be able to do it as a two-day event but the trail is more technically challenging then I remembered. Also, many steams were running high so I had to wade then and that takes more time. But now I can say I have backpack the Timberline Trail. It is approximately 40 mile with a combine gain and loss of 10,000 feet.