At Flybook, adventure isn’t just something we support; it’s part of our DNA. Nearly 70% of our team has worked as guides, outfitters, or managers in the outdoor industry, and every one of us understands what it means to build unforgettable experiences outside. From rivers to ridgelines, we’ve spent years leading trips, problem-solving in the field, and falling in love with the wild places that inspire our work today.
In this series, we’re sharing those adventures, and the lessons, tips, and hard-earned insights that came with them. Consider it trail-tested wisdom, passed directly from the Flybook crew to you.
In this post, we head to the base of Mount Hood in Oregon to hike the Timberline Trail.
By Zeb Millslagle, Flybook Software Engineer
The Timberline Trail is an amazing hiking trail that takes you fully around the base of Mt. Hood (also known as Wy'East) in just over 41 miles full of gorgeous wildflowers, waterfalls, creek crossings, glaciers and more. The trail can be experienced in a multitude of formats and enjoyed in many different ways.
My favorite is a single-day push, running around the whole loop. Starting early in the morning and heading counter-clockwise will help avoid a very sandy uphill finish, as well as ensure you cross some of the larger creeks before the snow melt makes them wider. Be sure to bring lots of snacks, and a filter to fill up on water. Avoid the bigger, silty creek runoffs and look for the clear glacier creeks to make filtering easier.
There is also a spigot and a bathroom about 15 miles in at Cloud Cap Campground. After this point, you can enjoy the rolling meadows and long downhill to the PCT. Taking an alternate trail will let you swing by Ramona Falls, where you can take a nice break before tackling the long climb back to Timberline Lodge.
No matter where the trail takes us, these adventures serve as a reminder of why we do this work: to help outfitters and adventurers focus on the moments that matter most. The outdoor community is where we come from, and it continues to shape and inspire everything we build at Flybook. We hope these stories fuel your next adventure, and maybe spark a few new ideas along the way.