This mountain is very special to us at Wy'east Wolfpack, which is why we included it in our name (Wy'east is the Native American name for Mt. Hood!) We've climbed to the summit, skied and snowboarded its slopes, camped on and foot-traveled around it many times! We want you to also have an amazing experience you'll remember forever, your own personal "rocking chair stories" :)
This is a world-class route and your jaw will be dropping around every corner! This is a very tough challenge, broken up into 3 days. There are several big climbs and descents, many creek/river crossings, altitude, and exposure to deal with. You should be able to comfortably complete a 10 mile trail run/ hike w/ 1-2k feet of climbing/descending, be familiar w/ the route in specific plus navigation and trail safety in general, etc.*
*This is NOT A GUIDED TRIP. All participants are responsible for themselves.
Meet at Top Spur Trailhead between 8-10 a.m. to drop off gear/supplies to be transported to Timberline Lodge and start your adventure! Take a short connector trail to Timberline Trail, then head counter clockwise on Timberline trail, descending to Ramona Falls to cool off. Next is a 10-mile section w/ two significant climbs leading to the Timberline Lodge. This is a tough, but spectacular, ~17 mile section on the west/southwest side of Wy'east. When you arrive to the chalet at the lodge make yourself comfortable w/ access to showers/clean clothes, plus recently renovated sauna, hot tub, and pool, as well as restaurant/bar. Friday night dinner is on your own. We hope you enjoy the luxury of this beautiful, historic building!
Coffee/Breakfast on your own, looking up at glorious Wy'east from the Timberline Lodge. Take advantage of the Lodge amenities before you set back out into the wilderness! Leave any gear on your bed that you want transported to Tilly Jane/Cloud Cap/back to your vehicle. Head out for this ~13 mile section, climbing to the highest point on the course over Gnarl Ridge before descending into the Cloud Cap campground.
Your camping gear will be awaiting you. Settle in to camp and relax while we prepare a nice dinner (vegan/gluten free options available). If you have specific food items you want, feel free to pack those in your gear and we will transport them to the cabin/campground. This will be a fun night on the NE side of the mountain!
Coffee/ Breakfast provided at the cabin/campground. Head out across the north side of the mountain through some of the most pristine meadows to finish off the loop and arrive back at your vehicle via the short Top Spur trailhead connector.
You just foot-traveled the whole way around Oregon's tallest volcano!
1-night @ Timberline Lodge (shared bunk room)
1-night @ Tilly Jane Cabin/Cloud Cap Campground (w/ personal camp gear)
Transported Gear/Supplies to multiple locations
Dinner and breakfast at Tilly Jane/Cloud Cap
Goodie bag of trail snacks (Trail Butter products)
Support from Wy'east Wolfpack staff who are very familiar w/ route + Hugs and High Fives :)
Cancellations up to 30 days before the trip start receive a full refund (minus $25 processing fee), or credit for future use.
Cancellations 48 hours to 30 days before the trip start receive 50% refund, or credit for future use.
Cancellations less than 48 hours receive no refund.
Cancellation due to uncontrollable environmental factors like hazardous conditions due to wildfires and/or excessive wildfire smoke will receive a full refund (minus $25 processing fee), or credit for future use.
The 42-mile Timberline Trail that encircles the great Wy'east (Mt Hood) is one of our very favorite trails, not to mention an absolute classic route around one of the most iconic peaks in the country. Approximately 42 miles and 10,000 ft of up and down is a seriously challenging feat made a lot more manageable and enjoyable by staying at the historic Timberline Lodge and Tilly Jane Cabin/campground along the way! We provide all the support and logistics to make this dream trip a reality, everything except being on trail with you!
Ages:
Date:
Dates:
Friday, Saturday, and Sunday
Jul 18, 2025
–
Jul 20, 2025
Time:
See what's included in this package.