In this special episode, Jeff Garmire and Derrick Lytle bring the laughs with The Jeffrey Awards—trail running’s greatest trophy! Join us as we hilariously crown winners in outrageous categories celebrating the best, worst, and downright weirdest moments of the trail running and ultra community.

Support us on Patreon. Patreon.com/freeoutside

🏆 Categories & Nominees:

Most Obvious New Race Director: Finn Melanson, Dylan Bowman, Jeff Garmire, Wes Siler

We Should Be Your Publicist Award: Camille Herron, UTMB, Spring Energy, Crazy Mountain 100

Most Tragic FKT: Katie Gunvalson (PCT fail on day 1), Eric Hallsten (AZT), Jeff Garmire (TRT), Joe McConaughy (JMT)

Walker of the Year: Mike Wardian (Appalachian Trail), Joe Corcione (Cocodona & Ouray), Callie Vinson (Cocodona), the guy who “ran” the length of Africa

Finally It Happened Award: Jasmine Paris (Barkley Marathons), Jeff Browning multi-day FKT, David Sinclair Pro Contract

Forgot It Happened Award: The Eclipse, Further Project, Ludo Hardrock, Olympics, Barkley 5 finishers, Kyle Curtin, Kelvin Kiptom

Double Track vs. Singletrack: Double Track, Singletrack

Who Is That Award?: Inya Ramadi, Vincent Boullard, Will Peterson (LT FKT), Rod Farvard, Jeff Mogavero

Most Destroyed Trail: Pacific Crest Trail (fires), Appalachian Trail (hurricane)

Owner of Zona (King of Arizona): Nick Fowler, Georgia Porter, Jamil Coury, Harry Subertas, Heather Anderson, Rachel Drake, Candice Burt

Courtney vs. Jim Award: Courtney Dauwalter, Jim Walmsley

They Still Run? Award: Andy Jones Wilkins, Jamil Coury, Billy Yang, Mike Foote, Dylan Bowman

Tara Dower East Coaster of the Year: Tara Dower, Allison Mercer, Will Peterson, John Kelly

Most Air Time Award: Dylan Bowman, Corrine Malcolm, Chris Warden, Leah Yingling, AJW

Hypocritical Hero: UTMB, vegan AT attempts, big brands hiding manufacturing practices, Michael Sunseri, climate change fundraisers and athletes

Hayden Hawks Ultra Runner of the Year: Hayden Hawks, David Roche, Jim Walmsley, Katie Schide, Courtney Dauwalter, Rachel Drake, David Sinclair, Jasmin Paris

Best New Podcast: Boulder Boys, Free Outside, Second Nature

Derrick Lytle Award: Greg Salvesen, Jeff Allen

Influencer of the Year: Ketone-IQ influencers, Matt Choi, Matt Johnson, Sage Canaday

Trail Town of the Year: Bend, Boulder, Flagstaff, Durango, Cedar City

Who won? Who deserved it? And who walked home with their head down? Don’t miss this—because anything goes!

Chapters

00:00 Introduction and Holiday Plans

05:57 Publicist Awards: Who Needs One?

11:57 Most Tragic FKT Attempts

17:59 Walker of the Year Awards

25:56 Finally It Happened: Celebrating Achievements

29:06 Memorable Moments in Sports

30:23 Record Breakers and Forgotten Achievements

32:03 Kyle Curtin's Impact on FKTs

35:03 The Who Is That Award: Unsung Heroes

42:41 Most Destroyed Trail: PCT vs AT

44:18 King or Queen of Arizona: The Nominees

50:59 The Joy of Unconventional Jobs

51:59 Celebrating Achievements in the Running Community

52:59 The Awards Show: A Lighthearted Discussion

53:59 The They Still Run Award: Who's Still in the Game?

01:00:01 The East Coaster of the Year Award

01:00:58 Most Airtime Award: Who Dominated the Conversation?

01:13:02 Humorous Race Commentary and Interviews

01:14:10 The Jeffrey Awards: Celebrating Achievements in Ultra Running

01:15:46 Hypocrisy in the Ultra Running Community

01:19:40 Traveling Athletes and Climate Change

01:22:30 The Hayden Hawks Ultra Runner of the Year Award

01:29:34 Best New Podcast and Future Awards

01:35:50 Innovative Live Streaming Ideas

01:36:24 The Jeffrey Awards: Celebrating Influencers

01:37:45 Marketing Strategies in the Influencer Space

01:38:57 Controversies in Running: The Case of Matt Choi

01:39:50 The Rise of Sponsorships in Trail Running

01:40:49 Matt Johnson: The Hybrid Athlete

01:42:04 Sage Canaday: The Ivy League Influencer

01:43:55 Trail Towns: The Best and the Worst

01:45:16 Predictions for the Future of Trail Running

I’m taking you along on a six-day, 150-mile adventure through Los Padres National Forest. It was a trip filled with poison oak, endless bushwhacking, and some questionable decision-making—like losing my hiking partner for a whole night. I’ll share everything, from battling overgrown trails to soaking in clothing-optional sespe hot springs, hitchhiking with a pigeon-loving driver, and trying not to let poison oak ruin the whole thing. This episode’s a bit experimental with trail audio clips mixed in, but hey, that’s how we roll.

Support the show on patreon! Patreon.com/freeoutside

takeaways

-Backpacking is a challenging yet rewarding experience.

-Getting lost in the wilderness can be both scary and enlightening.

-Resupplying in remote areas can lead to unexpected adventures.

-Nature can be harsh, with obstacles like poison oak and rough trails.

-The beauty of the outdoors often comes with its own set of challenges.

-Camaraderie in hiking can make tough situations more bearable.

-Planning is essential, but flexibility is key in outdoor adventures.

-Experiencing hot springs after a long hike is a unique reward.

-The journey is as important as the destination in backpacking.

-Every adventure teaches valuable lessons about nature and oneself.

Sound Bites

"We actually lost each other."

"I got poison oak."

"This is such a rough trail."

"We hitchhiked into Ojai."

"Thanks for listening."

Chapters

00:00 Introduction to the Adventure

02:52 Day One: The Journey Begins

05:55 Day Two: Lost in the Wilderness

09:08 Resupply Challenges and Unexpected Turns

12:04 Climbing and Nature's Obstacles

15:00 The Thorn Point Lookout Tower

18:05 Hot Springs and Final Days

21:13 Conclusion and Reflections

This week on the Free Outside podcast, I continue my epic journey through the month of Jeff with an extraordinary guest: Jeff Jenkins, professional traveler, TV host, and all-around inspiring human. We dive into Jeff’s journey from taking his first flight at 20 years old to becoming a globe-trotting storyteller featured in Forbes and the New York Times.

We talk about his first transformative experience in Japan, his approach to capturing content that inspires others, and how he’s opening up the travel world for plus-size adventurers. Jeff shares behind-the-scenes insights into his Nat Geo TV show, his strategies for manifesting big dreams, and what it takes to build a brand that’s authentic, inclusive, and impactful. Whether you’re a dreamer, a traveler, or just love hearing about chasing the impossible, this episode will leave you motivated to live boldly.

Support the Free Outside Podcast: Patreon.com/freeoutside

Follow Jeff Jenkins on the internet: https://www.instagram.com/chubbydiaries/?hl=en

takeaways

-Travel can be daunting, but the right destination can inspire courage.

-Experiencing a new culture can broaden one's perspective.

-Building a brand is more important than just being an influencer.

-Daily affirmations can help manifest dreams and goals.

-Traveling for content can sometimes overshadow the joy of exploration.

-Shooting a TV show involves a rigorous schedule and preparation.

-Authenticity in relationships is crucial amidst growing fame.

-Inclusivity in travel accommodations is essential for all body types.

-Persistence is key to success in content creation.

-Travel teaches us that despite cultural differences, we are all fundamentally the same.

Sound Bites

"The travel bug bit me there."

"I love Korean barbecue."

"I want to go to Antarctica."

Chapters

00:00 The Journey Begins: Jeff Jenkins' Early Travel Experiences

07:43 Building a Brand: From Influencer to Professional Traveler

13:44 Culinary Adventures: Memorable Meals from Around the World

19:55 Behind the Scenes: The Reality of Shooting a TV Show

25:55 Lessons from Travel: Common Humanity and Connections

32:08 Future Aspirations: Bucket List Destinations and Content Creation

38:05 Advocacy for Inclusivity: Changing the Travel Industry for All

keywords: travel, content creation, Jeff Jenkins, Nat Geo, travel experiences, cultural discoveries, travel advice, travel industry, personal growth, inclusivity