The Trailhead

Geologist and Pro Athlete Dillon Osleger on the Hidden History Written Into Every Trail

June 23, 2026·1h 5m
Episode Description from the Publisher

Dillon Osleger is a geologist, professional mountain biker, and longtime trail steward whose debut book, Trail Work: Restoring the Paths and Stories of America's Public Lands, uncovers the buried history beneath the trails we run, ride, and take for granted. In this conversation, Zoe and Brendan get into why nobody wants to do the unglamorous work of maintenance (and the Kurt Vonnegut line that nails it) and how to read a trail like a layered history book. Dillon decodes what is hiding in plain sight, from barbed wire patents that date a fence to within two years, to the segregated CCC camps you can spot in the stonework, to the Indigenous place names that outlast every map. Along the way: what is quietly erasing two-thirds of America's historic trails, an extremely unhinged riff on trailmaxing as the next men's wellness trend, and a genuinely useful answer to the question most of us are too sheepish to ask, which is how do you actually start doing trail work. This episode is brought to you by Running Warehouse, your one-stop shop for trail shoes, vests, poles, and the anti-chafe stuff you forget until mile 40. Join the UltraSignup Club: https://www.runningwarehouse.com/?from=ultra The Trailhead is part of the UltraSignup Podcast Network.

Podzilla Summary coming soon

Sign up to get notified when the full AI-powered summary is ready.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.

Listen to This Episode

Get summaries like this every morning.

Free AI-powered recaps of The Trailhead and your other favorite podcasts, delivered to your inbox.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.