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.
The report includes excellent photos so you really get a feel for what to expect.
Check it out:
TIMBERLINE TRAIL – MOUNT HOOD WILDERNESS, OR (40 MILE LOOP)
Similar adventures in the Pacific N.W. include the Wonderland Trail around Mt Ranier and / or a partial circuit around nearby Mt Adams.