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As the Timberline encircles Mt. Hood it offers views of the glacier-capped mountain from every side. The dramatic volcanic geology makes for beautiful scenery, especially on the higher eastern side of the loop.
Just over an hour from Portland, the Timberline Trail is super easy to access. There's free parking at the Timberline Lodge trailhead or you can even take public transit. It's a loop so you'll finish where you started - no complicated car shuttles necessary.
Dispersed campsites are generally easy to find every mile or so. Most sites have access to water since the trail crosses many streams and rivers on its way around the mountain.
The Timberline Trail crosses many glacial streams and rivers, and during peak snowmelt they may be hard or impossible to cross safely. Check conditions before starting, know safe crossing techniques, and plan to cross the biggest ones early in the morning.