Timberline Trail Around Mount Hood From Cloud Cap Inn is a 38.6 mile moderately trafficked loop trail located near Mt Hood, Oregon that features a waterfall and is rated as difficult. The trail offers a number of activity options and is accessible year-round.
Did this trail as part of the timberline trail in 2015. Great trail- very challenging if not in shape. Had one of our hikers catch a ride back to the timberline lodge before Elliot glacier. Did 18 miles in late august
Note: this is basically the eastern part of the circumnavigation of Hood.
Feel like something challenging that'll leave you sore and amazed? Start out at Timberline Lodge, and head right at the PCT sign. 15 challenging miles later, you'll have crossed streams, battled heavy winds, had amazing views of Elliot Glacier, hiked Gnarl Ridge, and arrived at Cloud Cap Inn. Park a car and do it as a point-to-point. Or if you're training, hell, try all 30 miles of pain!
It's beautiful, though I'm not sure I'd make the trek in the winter months if not *completely* prepared: I've done it as a hike in the warmer months, but you might want to have a little mountaineering knowledge if you're trying it in the winter.