Adult Cross Country, Halloween Chaos, and Santa Sees Javelina 100

31/10/2025 18 min

Listen "Adult Cross Country, Halloween Chaos, and Santa Sees Javelina 100"

Episode Synopsis

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.Chapters00:00 The Montana Cup and Cross Country Racing02:41 Post-Appalachian Trail Recovery and Training05:55 Halloween Race Experience and Costumes11:25 Pacing a Runner and Celebrating Success14:07 Life Hacks and Upcoming EventsSubscribe to Substack: http://freeoutside.substack.comSupport this content on patreon: HTTP://patreon.com/freeoutsideBuy my book "Free Outside" on Amazon: https://amzn.to/39LpoSFEmail me to buy a signed copy of my book, "Free Outside" at [email protected] the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outsideWebsite: www.Freeoutside.comInstagram: thefreeoutsidefacebook: www.facebook.com/freeoutside