Our 9th Trip to Mile 0

I have been thinking about Mile 0 Fest since before it ever had a name.

Before the stages. Before I had favorite restaurants and bars and friends that actually lived on the island. Before the schedules and an app. Before anyone knew how big it would become.

The idea alone was enough.

Taking the music I loved and carrying it as far south as it can possibly go. All the way to the end of the road. Mile Zero. I had tossed out the idea of an alternative the majestic mountains of Steamboat and a more tolerable climate for years. I never had the capital or genius to pull it off the way Kyle Carter has.

The dragon we created in year one has been chased ever since. Literally pillaging Duval like Texas pirates. Overwhelming the jaded locals with our overt kindess and loud music. They didn't know what hit them. Now they know to expect it. The exotic is now familiar. To both sides.

I have been to every one. That matters to me. Not in a checklist way but in a lived in way. Watching something grow from a spark into a tradition you plan your year around. Feeling the rhythm of it settle into your bones. Knowing when you step off the plane that you are exactly where you are supposed to be.

Key West still holds magic for me.

There is the ever present pull of Ernest Hemingway, whose ghost feels baked into the streets and bars and salty air. There is the poetry of Jimmy Buffett, whose songs feel less like entertainment here and more like documentary. I hear them differently when I am standing where they were written from. When the breeze and the rum and the laughter all line up just right. The spirit of Jerry Jeff permeates it all. Freewheeling and wheels off for a week is a good reminder to live life by grabbing it by the horns.

There is also the reality of pirates. The sense that this place has always been a little lawless and a little free. A town that does not apologize for being exactly what it is. Add to that the charm of the locals who have seen it all and still welcome you in like an old friend, and I understand why people fall in love with this island and never quite let go.

For me, taking this music south each winter has become one of the great highlights of the year. It is a reset. A reminder of why we do this in the first place. Great songs, honest artists, long conversations, old friends, new pals, All of it. The late nights paired with the sunrises that sneak up on you when you thought the night was still young.

Every year feels a little different and somehow exactly the same. Nothing may ever top 2018 or 2020. But that doesn’t mean the other years and future years aren’t overwhelmingly amazing in their own right.

The stages change. (Two on Truman Lawn this year). The lineup evolves. The crowd ebbs and flows. But the feeling never wavers. That shared understanding among everyone involved that this is special. That this is not just another festival stop. It is a pilgrimage.

This year will be no different.

I am excited in that familiar way that starts months out and grows louder the closer it gets. Excited to see friends I only ever see here. Excited to hear songs echo down Duval Street. Excited for the food, the sights, the smells. The people. Excited to be reminded once again why Key West continues to pull us all back.

The road always ends here. Literally. But it also starts here too. And every winter, I am grateful to follow it all the way down and back up again. See you on the island.