Clever Hiker updated details in 2024:

Distance: 38.3-mile loop
Time Needed: 3-4 days
Highest Elevation: 7,350 ft. Timberline High Point
Lowest Elevation: 3,300 ft. Near Ramona Falls
Elevation Gain (approx.): 9,000 ft.
Best Time to Hike: July-September
Permits: Yes (May 15th to October 15th)
Difficulty: Challenging

Permits

Permits are required for overnight trips on the Timberline Trail from May 15th to October 15th, but they are free and can be found at trailheads around Mt. Hood. Simply fill one out before you hit the trail. Some trailheads do require a Northwest Forest Pass for parking.

Jon posted a detailed trip report on their August 2019 circuit of Oregon’s highest peak. It’s close to Portland.

This report is all you need to organize that adventure for yourself.

Plenty of climbs and descents. Quite a few creeks crossings. Not what we’d call an easy week.

They started and ended at Timberline Lodge. And hiked clockwise.