It all started on April 11, 2008. I drove up to Timberline Lodge on Mount Hood for the first time to grab dinner and watch the sunset with my fiancé. After enjoying the meal, I hiked up above the lodge with my camera.

27 at the time, I previously never felt a desire to climb mountains. And then something happened I can't fully explain: the mountain "spoke" to me. As alpenglow radiated off Hood’s upper slopes, I was struck by a feeling to climb it. 

The following Monday I went to work, told my friends what happened, and soon made a reservation for four with Timberline Mountain Guides to climb Hood's south side that June. Our group trained for two months and successfully reached the summit.

The next summer, we decided to kick things up a notch and climb five mountains - Hood, St. Helens, Adams, South Sister, and Rainier - and the "Pentaquest" was born. In the years since, we continued the five summit-tradition with many others joining the group. Some are only able to go on one training hike, while others climb several higher peaks or join multi-day backpacking trips...but all are Pentaquesters, and all agree the best way to experience Cascadia is from a mountain top or hiking trail.

- Dan Douthit