Paddy O’Leary on Winning the 112th Dipsea; Trail Running Film Recs; & the Broken Arrow Skyrace (Ep.177)

First run in 1905, the Dipsea is the oldest trail race in the US. Its course takes runners from Mill Valley, CA to Stinson Beach, 7.4 miles separated by 700 stairs, shortcuts, thickets of poison oak, technical singletrack, and stretches of trail with nicknames like “Suicide,” “Cardiac,” and “Insult.” The race’s unique handicap format gives certain runners head starts based on age, gender, and prior performances, meaning that logging the fastest time on the course doesn’t always ensure a victory.

Unless you’re Paddy O’Leary this year. The North Face athlete took home both trophies at the 112th Dipsea a little over a week ago, so I sat down with him to talk about the race’s storied history; some of the eccentricities that make it so singular; and the various films that have been inspired by it. We also breakdown the Broken Arrow Skryace, which wrapped up its weekend of races on Sunday, and a whole lot more.


  • Broken Arrow Recap (2:07)
  • Fun Storylines Coming Out of the Weekend (8:53)
  • Eleanor Scholz’s Lupine Shadow Lamp Trophies (11:53)
  • The Dipsea (14:14)
  • Shortcuts, Handicaps, & Film Recs (20:52)
  • Western States Pacing Duties (31:19)