The Run Club
PodcastsRun ClubsVideosTagsAthletesRacesCalculators
    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.

    Hosted By

    UltraSignup

    Margaret Glaspy on Pain Caves, Typewriters, and Running on Tour

    Margaret Glaspy on Pain Caves, Typewriters, and Running on Tour

    September 1, 2026
    55m

    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. 

    More from The Trailhead

    Doing It The Hard Way is the Point - With Writer Sam Robinson

    Doing It The Hard Way is the Point - With Writer Sam Robinson
    August 18, 2026

    What If the Hero's Journey Is the Wrong Story? With Heather Hansman

    What If the Hero's Journey Is the Wrong Story? With Heather Hansman
    August 4, 2026

    Is Running a Religion? A 1,400-Mile Pilgrimage Around Ireland with Author Adharanand Finn

    Is Running a Religion? A 1,400-Mile Pilgrimage Around Ireland with Author Adharanand Finn
    July 21, 2026