
Show Notes
Trails are hewn from granite, carved into sandstone cliffs and engineered into our most iconic landscapes. Other times, they offer just the faintest hint of the passing of those before us. Either way, we often take their existence for granted. Today with the help of author Dillon Osleger we ask the seemingly simple question “Why do trails exist?”
Read Dillon’s book: Trail Work
Support comes from
Oboz: Comment on the Roadless Rule by Sept 21
Kuat Racks
Kodiak Find Kodiak at kodiakcakes.com or your local grocery store
Ka’Chava Go to https://kachava.com and use code DIARIES for 15% off your next order.
Diaries+ Members-- Their support is powering the Diaries- thank you! You can join today.
More from The Dirtbag Diaries
We’ve all been there: in a tent, in the dark, in the middle of nowhere. It’s quiet, peaceful– until you hear a sound. Was it the wind? Your imagination? Or something far worse? True terror lies in the unknown. Welcome to our annual Tales of Terror.
In October of 2025, the Trump administration green lit the Ambler Road in Alaska, a proposed mining access road that would cut through 211 miles of pristine Alaskan wilderness in the Brooks Range, crossing over 3,000 waterways and could forever change access to subsistence resources in Northwest Alaska. In collaboration with More Than Just Parks, the Dirtbag Diaries presents a two part story. Karmen Monigold and John Gaedeke each rely on the southern Brooks Range for their livelihood and have joined a grassroots effort to fight back against the Ambler Road. A pair of young conservationists, Robert Lester and Ben Kaden set out to walk the proposed Ambler Road and experience the wilderness first hand.
When Somira Sao and James Burwick were expecting their first child, they made a vow not to stop traveling-- and they took that promise to the extreme. In 2009, after two years of living in a van traveling around South America, they took their growing family and moved onto a 40' monohull sailboat. Four years later, they had navigated a de-masting off the coast of Chile, sailed around the globe, added more kids to the mix, and created a unique philosophy on adventure parenting.
We never know where our life’s important lessons will come from. After years of chasing first ascents in the PNW Cascade mountain, Cam Fenton stumbles upon a new focus for his mountain exploits: grizzly bears. For Emma Brophy, collecting red rubber bands while on a 600 mile river trip down the Thelon River in Canada becomes a reminder of how far she’s traveled.
Drew Smith is one of the most highly respected outdoor adventure photographers in the game. His work has brought him to more than two dozen countries, and his skills in the mountains make him a top choice for professional athletes looking for a photographer who can keep up. In this episode, he takes us through four projects that have shaped his career as a creator, and we talk about the important lessons he's learned along the way.