Mt Hood Timberline Trail
$1250 | July 30-Aug 2nd 2026 | 12 spots | Men & Women
Sign up by May 1st 2026
“ May your trails be crooked, winding, lonesome, dangerous, leading to the most amazing view. May your mountains rise into and above the clouds.”
Schedule
Thursday Evening-Overnight Cooper Spur Mt Resort Cabin
Friday morning-30 min drive from Cooper Spur to Cloud Cap on the Northern flanks of Mt Hood National Forest. Hike 27 miles/Overnight Timberline Lodge
Saturday morning-hike 15 miles to Cloud Cap. Drive car back to Timberline Lodge. Pool, dining, hot tub, R&R.
Sunday morning-breakfast buffet at Timberline Lodge. Half day Rafting excursion on the Deschutes River. Arrive home Sunday night.
Route
Beginning and ending at the old Cloud Cap Inn parking lot, we will leave our cars overnight and start our 1st leg of the Timberline Trail heading counter clock wise around the western side of the mountain. We will forge water crossings, and gain most of our elevation towards the latter part of our day.
After overnighting at Timberline Lodge, we will begin our 2nd day with a long descent crossing White River, traversing through Mount Hood Meadows, scrambling up a long ridge and back to our cars at Cloud Cap.
In August of 2022 Cara, Griffin and I ran/hiked the Timberline Trail in one day, finishing in 15 hours. Breaking this route up into 2 days is very do-able!
More details to come
Hike Details
Distance: 44 miles, 10,340 feet of elevation gain
Completion Time: 2 days
Location: Mount Hood, 1.5 hours from Portland, Oregon
Trail Type: Loop
Scenery: Beautiful old forests, sprawling meadows full of wildflowers, some rocky/sandy/exposed sections. This hike really has it all and shows you how diverse the area around Mount Hood is. And the best part? Constant, ever-changing views of the mountain throughout the hike.
Terrain: Significant unbridged water crossings, dirt paths, sandy paths, and rocky terrain.
Criteria & Pricing
An excellent cardiovascular base and extensive hiking/running experience.
A minimum of 8 spots must be filled by May 1st 2026 for this Adventure to take place.
$250-Due at time of booking
$500-1st Installment due May 1st
$500-2nd Installment due June 1st (if you have to cancel after June 1st you will be refunded your first installment only)
Included
Climbing gear checklist
3 Nights Lodging in Cabins/Lodge with shared double beds and bunk beds
Guided Climb
Timberline Trail Medal (as shown above)
One morning buffet breakfast
Half Day Rafting on the Deschutes River
The right to say under your breath, every time you lay eyes on her; Mount Hood….you mother effer.
Not Included
Transportation (car-pooling is encouraged)
Meals, other than buffet breakfast