First it should be noted that the Timberline Trail is officially closed over Eliot Creek ever since a washout occurred in 2006, eradicating that portion of the trail. However, one can still negotiate the entire circuit by crossing the Eliot area at your own risk. Do a quick search and lots of info will pop up from Oregon Hikers and other sources. See below for more information on this crossing. Otherwise we found the Timberline trail to be quite delightful and easily doable in two days, although in our case with the drive we didn't start the hike CW from Timberline lodge until noon on day 1. Various sources say the Timberline is 40 miles with 8,000 feet of climb. We started our hike on August 17.