Walk the Timberline Trail around Mount Hood
A friend has invited you to do this with them.
This trail of about 40 miles circles Mount Hood through west-side Cascade forest and alpine meadows, past waterfalls and wide views. Most of it was built by the Civilian Conservation Corps in the 1930s.
DemandingUnder £100 / $130A few weeksOutdoorsAlone or with othersOregonJuly to October
How to start
- Read the Forest Service's Timberline Trail page and check its alerts for fires and closures.
- Walk one stretch as a day hike first, then plan the full loop over several days.
- Pick up a free, self-issued wilderness permit at the trailhead, and check whether your trailhead charges a day-use fee.
Where to go
We opened this link on 30 October 2026 and found it to be what we say. Dates, places and prices are on the official page, where they stay up to date.
Plan this
Pick a day, or a month, and we will set out how to get ready, step by step, with a date and a reason for each. Projects run over months and stall without a rhythm, so the plan sets milestones you can see.
Read next
Six pairs of shoes and seven months on the Pacific Crest Trail took Nancy Zelick from Mexico to Canada
How a retired Intel researcher from Baker City, Oregon, walked the Pacific Crest Trail from Mexico to Canada in about seven months: the snow, the gear, the food and why she thinks pace mattered more than youth. How to start multi-day hiking, or build towards a long trail if you already walk.
Walking holidays for beginners: how to choose a route you'll actually enjoy
A beginner's guide to walking holidays: UK National Trails such as the South Downs Way and Hadrian's Wall Path, the Camino to Santiago, US National Park trails, how to choose a daily distance, baggage transfer, and where the Ramblers fit in.