Uploaded June 2025 | Updated September 2026, 2 weeks ago
Dylan Bowman returns to the Singletrack Podcast for a wide-ranging, in-person conversation from our Olympic Valley, CA studio just days before the 2025 Western States 100.
As the founder of Freetrail and a key figure behind TrailCon, Dylan has spent the last few years shaping the conversation around what trail and ultrarunning can—and should—become. In this episode, we dive deep into the evolution of the sport, how media and storytelling are influencing the culture, and what role platforms like Freetrail play in that transformation.
We also discuss Dylan’s role as a lead broadcaster for the Western States 100 live stream, what goes into bringing the race to a global audience, and how coverage has evolved since his own racing days. With one foot in the athlete camp and the other in media and community-building, Dylan brings a nuanced perspective on where the sport is heading—from prize purses and professionalism to inclusivity and sustainability.
Finally, we get Dylan’s bold predictions about the future of trail and ultrarunning. Are we really at a crossroads? Is the golden age still ahead?
Partners:
* @nordarun - check out the 005: the lightest, fastest, most stable trail racing shoe ever made (nordarun.com/)
* @gorewear - use code SINGLETRACKPOD30 at checkout on their website to get 30% off your purchase.
* @naak - use code SINGLETRACK20 at checkout on their website (naak.com/) to get 20% off your purchase.
* Raide - Making equipment for efficient human-powered movement in the mountains (raideresearch.com/)
Photo: @sh1tinthewoods
Follow Singletrack on Instagram:
instagram.com/runsingletrack
Subscribe to Singletrack on Apple:
podcasts.apple.com/us/podcast/singletrack/id1572382413
Subscribe to Singletrack on Spotify:
open.spotify.com/show/7jAsWCRNSCU8nh81vrAaC2?si=3ac02e4e32b946c4
Dylan Bowman returns to the Singletrack Podcast for a wide-ranging, in-person conversation from our Olympic Valley, CA studio just days before the 2025 Western States 100.
As the founder of Freetrail and a key figure behind TrailCon, Dylan has spent the last few years shaping the conversation around what trail and ultrarunning can—and should—become. In this episode, we dive deep into the evolution of the sport, how media and storytelling are influencing the culture, and what role platforms like Freetrail play in that transformation.
We also discuss Dylan’s role as a lead broadcaster for the Western States 100 live stream, what goes into bringing the race to a global audience, and how coverage has evolved since his own racing days. With one foot in the athlete camp and the other in media and community-building, Dylan brings a nuanced perspective on where the sport is heading—from prize purses and professionalism to inclusivity and sustainability.
Finally, we get Dylan’s bold predictions about the future of trail and ultrarunning. Are we really at a crossroads? Is the golden age still ahead?
Partners:
* @nordarun - check out the 005: the lightest, fastest, most stable trail racing shoe ever made (nordarun.com/)
* @gorewear - use code SINGLETRACKPOD30 at checkout on their website to get 30% off your purchase.
* @naak - use code SINGLETRACK20 at checkout on their website (naak.com/) to get 20% off your purchase.
* Raide - Making equipment for efficient human-powered movement in the mountains (raideresearch.com/)
Photo: @sh1tinthewoods
Follow Singletrack on Instagram:
instagram.com/runsingletrack
Subscribe to Singletrack on Apple:
podcasts.apple.com/us/podcast/singletrack/id1572382413
Subscribe to Singletrack on Spotify:
open.spotify.com/show/7jAsWCRNSCU8nh81vrAaC2?si=3ac02e4e32b946c4
