Singer-songwriter Margaret Glaspy joins Zoë and Brendan to talk about the strange and surprisingly rich overlap between running and making art. She shares how watching her mom run planted the seed early, growing up close to the Western States course, how Courtney Dauwalter and Addie Bracy helped draw her into ultrarunning, and why learning to sit with discomfort has changed far more than her athletic life.

Margaret also talks about quitting social media, writing songs on a typewriter, finding solitude in anonymous hotel gyms, and the logistical challenge of training while touring in a van. Plus: the financial risks of falling on your guitar-playing hand, the unexpectedly deep musician-to-ultrarunner pipeline, and what Margaret might learn from how ICU nurses train for ultras.

Sam Robinson writes the Substack Footnotes, works as a content designer at YouTube, and has a PhD in seventeenth-century science, religion, and philosophy, which makes him exactly the right person to ask why we're all trying so hard to optimize a sport whose whole appeal is that it's beautifully pointless. Zoë and Brendan get into the tension with him: distance running rewards incremental gains and deferred gratification, and it's also the least efficient way imaginable to get from point A back to point A. Sam talks about racing above Stinson Beach with his head down, missing the view; about eating a protein bar in the shower at 4:58 a.m. to make a 7:30 meeting; and about how a three-year-old and a torn meniscus have both forced a slower relationship with the sport.

The back half turns to Sam's piece on the fragility of type two fun and the male friendship crisis, what happens to shoulder-to-shoulder friendships when the run club scatters and the knee gives out, and whether shared mileage alone can hold a community together. Along the way: Robert Caro, Oliver Burkeman, Benjamin Franklin prosecuting his breakfast, and the unsettling possibility that morning-routine influencers have never actually seen American Psycho.

Read Sam at footnotes.substack.com. This episode is brought to you by Running Warehouse - join our club here.

Heather Hansman is an award-winning outdoor journalist, an Outside columnist, and the author of Downriver and the bestselling Powder Days. Her new book, Fierce Country: The Untold Story of Three Women Who Ignited America's Love for the Wild, is out now.

In this conversation: the therapist who mapped the heroine's journey, and the very famous mythologist who told her women don't need one; Georgie White swimming Grand Canyon rapids in 1945 in tennis shoes and a couple of hard candies; why there always seems to be exactly one available spot at the top for a woman, and what that has to do with the way we talked about Rachel Entrekin winning Cocodona outright; topophilia, or what happens when the love of your life turns out to be a landscape; and whether the American myth of the lone tough guy summiting the mountain is, frankly, a pretty boring story.

This episode is brought to you by LMNT. Go to drinklmnt.com/UltraSignup for a free sample pack with any order.

Featured race: the Bear Canyon Trail Run in Sandy, Utah, on Saturday, October 10. Formerly the Corner Canyon Ultra, now with a new name and a new course. The 11 Mile Classic climbs over 4,000 feet in five miles, the 20 Mile Challenge runs that loop twice, and there's a 5K if you'd like to keep your quads. Every dollar raised goes to an individual or family facing serious hardship, nearly $70,000 to 13 recipients since 2013. Registration closes Wednesday, October 7. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.

Adharanand Finn is an award-winning journalist and the author of Running with the Kenyans, The Way of the Runner, and The Rise of the Ultra Runners, and his forthcoming book The Running Pilgrim chronicles the 1,400 miles he ran around Ireland in 68 days.

In this conversation, Zoe and Brendan talk with Adharanand about what Kenyan, Japanese, and ultrarunning cultures taught him about community and staying in the moment, why a pilgrimage is basically an ultra with better theology, the science of why running with other people feels easier, ultrarunning's weird romance with suffering, and the definitive (and expanding) playlist of songs about running.

This episode is brought to you by Running Warehouse, where you can find everything you need to survive summer running, from vests to socks to a frankly irresponsible number of gels. Shop through the link in our show notes.

Featured race: The Oregon Outback 230 is a 230-mile point-to-point journey from the eastern Cascades to Lakeview, Oregon, through the largest dark sky sanctuary in the world, happening July 16 through 21, 2027, with a 120-hour cutoff. Registration closes July 1, 2027. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.

Anastasia Wilde is a Missoula-based adventure photographer who has spent the last five years shooting the country's biggest 200-mile races like Bigfoot, Tahoe, Cocodona, and hiking up to eight miles into the backcountry with thirty pounds of gear to photograph runners at their most unfiltered.

In this conversation, Anastasia tells us how a Costco camera kit and a suspiciously well-timed $500 raffle win turned a middle school music teacher into one of ultrarunning's most prolific race photographers, why the mid- and back-of-pack will tell a stranger with a camera things they haven't told their families, the memory card catastrophe at the Bigfoot finish line she still thinks about, whether AI will ever make any of us look good while running (no), and what it means to photograph someone crying alone at sunrise on their way to a five-year buckle.

This episode is brought to you by LMNT and their new lemonade iced tea flavor. Get a free sample pack with any order at drinklmnt.com/UltraSignup.

This week's featured race is the Machete Muertos 200 at Lake Perris, California, starting Wednesday, October 28. 200 miles, 44,000 feet of climbing, and a 96-hour cutoff at one of the toughest 200-milers in the country, part of Machete Madness's Día de los Muertos celebration. There's also a 100-miler, a 50-miler, and 10- and 20-mile ruck divisions, with free family camping, free professional photos, and no pacer fees. Registration closes Friday, October 16. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.

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.