I thought I was done racing this year… but apparently Montana had other plans. Two weeks after Allison Mercer introduced me to cross country running, I found myself signing up for the Montana Cup — an annual, statewide, adult cross country throwdown where Bozeman, Missoula, Billings, and the rest of the Montana cities go head-to-head for glory. In this episode, I talk about my first hard 5K in twenty years, how I tried to re-train my calves after the Appalachian Trail, and whether my 35-year-old self can outkick my 14-year-old PR. Spoiler: probably not. But that’s not all — I also recap my Halloween weekend crewing at Javelina Jundred, where I became the self-proclaimed Ice Daddy, lost a costume contest as a horse, and ended up pacing a stranger to his first 100-mile finish while dressed as Santa. Because of course I did. There’s a life hack, a shout-out to my sponsors, a Blue Jays World Series dream, and an announcement for the return of Month of Jeff and the Jeffrey Awards. So grab a coffee (CS Coffee, obviously), lace up those Janji shorts, and join me for another chaotic, slightly overcaffeinated episode of the Free Outside Show. Chapters 00:00 The Montana Cup and Cross Country Racing 02:41 Post-Appalachian Trail Recovery and Training 05:55 Halloween Race Experience and Costumes 11:25 Pacing a Runner and Celebrating Success 14:07 Life Hacks and Upcoming Events Subscribe to Substack: http://freeoutside.substack.com Support this content on patreon: HTTP://patreon.com/freeoutside Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF Email me to buy a signed copy of my book, "Free Outside" at
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