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.

Dr. Nick Tiller is an exercise scientist at the Lundquist Institute at Harbor-UCLA, a two-decade ultrarunner, and the author of The Skeptic's Guide to Sports Science and the new The Health and Wellness Lie.

In this conversation: why ultrarunning is, by Nick's cheerful admission, not actually good for you, and why we keep signing up anyway; the red flags that should trip your bullshit detector in 2026; the great protein panic and how a "health halo" turns a Pop-Tart into a recovery food; what the evidence does and very much doesn't say about AG1; KT tape, cupping, and the slippery ethics of selling someone a placebo; and how to stay skeptical without curdling into a cynic whose brain has fallen out.

This episode is brought to you by LMNT, the new Lemonade Iced Tea flavor has been quietly fixing our hydration and our 4pm coffee regrets; grab a free sample pack with any order at drinklmnt.com/UltraSignup.

Featured race: the Ode to Laz Michigan Backyard Ultra, a 4.167-mile loop run every hour on the hour through 8,000 acres of Holly State Recreation Area in Holly, Michigan, on Saturday, July 18. The only way to win is to be the last runner standing, which is why the motto is "finishing last means the most." If you're backyard-curious but not ready to sign over your soul, the Oak Flats 3-hour option lets you dip in for one, two, or three loops. It's a championship-affiliated race, so the winner takes a silver ticket toward the USA national backyard team. Registration closes Thursday, July 16. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.

Ben Ratliff is a former New York Times music critic, a writing professor at NYU, and the author of Run the Song: Writing About Running About Listening, longlisted for the National Book Award and named a finalist for the PEN/Diamonstein-Spielvogel Award for the Art of the Essay, which chronicles what he hears when he brings music into his near-daily runs through the Bronx.

In this conversation, Zoë and Brendan talk with Ratliff about why running made him a better listener, and why the optimal-BPM running playlist is, by his lights, beside the point. He makes the case for listening as active attention rather than ambient wallpaper, explains why some of the slowest and quietest music turns out to be the most enlivening to run to, and pushes back on the idea that "good taste" is something you can buy. Along the way: defamiliarizing a song until it sounds brand new, the strange kinship between a long run and a long DJ set, and how a career critic ends up running to everything from jazz to Ice Spice.

This episode is brought to you by Running Warehouse, where Zoë gets basically all her summer running gear, vests, socks, hats, shirts, and a frankly irresponsible number of gels, with fast shipping and a return policy run by actual humans.

This week's featured race is the FCA Endurance Race in Oakwood, Georgia — a choose-your-own-adventure event on a flat, one-mile paved loop around the University of North Georgia's Oakwood campus. Pick your distance: a 5K, a 10K that detours onto dirt and a stretch of cross-country trail, or a timed race of two, four, six, twelve, or twenty-four hours, with some durations offering a 6 p.m. start so you can run straight into the night. It all happens Saturday, June 6, 2026, and registration stays open right through race day. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.