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    The Trailhead

    The Trailhead

    About

    The Trailhead isn't your typical trail running podcast—we're not dissecting splits or debating race strategies. Instead, hosts Zoë Rom and Brendan Leonard take you straight to the heart (and funny bone) of the sport, celebrating the people, stories, and quirks that make trail running so special. With a mix of humor, heart, and a little irreverence, we explore the personalities, people, artists, and everyday athletes who give the sport its soul—because trail running is about more than just the miles.

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

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

    June 23, 2026
    1h 5m

    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.

    The Trailhead is part of the UltraSignup Podcast Network.

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