Mile 0 26 - Halftime Report

(It actually happened. Someone blew out their flip flop. No reports of a stepped on pop top).

Key West showed up sideways this year.

Cold and blustery just like the rest of the country. But cold down here is still relative and warmer than back home. It does feature, however, the kind of wind that doesn’t care where you’re from or what you packed. It rattles flags, cuts through alleys, and makes even the most hardened locals admit that this is not the usual deal.

It doesn’t slow anything down. Mile 0 folks just pull their collar up and keep chasing music and good times.

When you hit the island you immediately start negotiating with Cuban coffee. Down here it’s not a beverage; it’s an agreement. Tiny cup, serious intent. Drink it fast and you’re steady. Drink it slow and you begin to levitate. Like seeing Stephen Wilson Jr but in liquid form.

Down here, clocks are broken and time stops behaving. There aren’t really days…but rather chapters and moments. You can make plans but Mile 0 doesn’t unfold in order. It introduces characters.

Our anchor appears behind the bar each year. Stephanie moves with purpose, like she already knows how this week is going to go. Pours clean, smiles, always makes eye contact. Keeps the place humming without ever raising her voice.

She remembers your drink after one order. Remembers your name after two. By the third, she’s asking where you’ve been all day like she’s genuinely curious. Because she is. When the wind kicks up and everyone complains, she shrugs and reminds us all that we’re lucky to be here.

Like us, she’s been here every year. Long enough to see the same people return every year looking older but happier. She pours a drink a little heavier when the song on the speakers hits just right. Especially if it’s American Aquarium. When someone asks what she recommends, she says, “Whatever helps you have a good time.” Great advice from a bartender. And for life.

The gift shop hoodie is a big player this year so far. It’s cheap, tacky and loud. Like the music we all despise. Sometimes both are purchased purely out of necessity.

And it works. Instantly. Like flipping a switch. Suddenly the wind is manageable. The night stretches back out. The hoodie becomes a hero…one you will deny loving later, but will pack on every future trip just in case. Key West in a neon Miami Vice style script. It’s part of your being now.

It smells faintly of salt air and bad decisions. It gives life anyway. Just like the town itself.

There’s a waitress who tells you she’s from New York, but she says it like she’s telling a joke she’s already over. She’s fast like muscle memory. Orders land before you finish speaking. She’s in her 70s and moved down here in the 70s. She calls everyone “hon” without irony.

She talks about winter like it’s a past relationship she learned from but doesn’t miss. When the wind rattles the windows, she laughs and says, “it could be worse.” She’s right.

She refills your coffee exactly when you need it and disappears exactly when you don’t. That’s professionalism.

The acoustic sets bring out the ongoing discussion: talking during quiet songs. The wind makes people huddle. The music asks for attention. Opinions are exchanged. The right etiquette is to take it away from those locked in listening. But, down here this year that seems to merely be a suggestion.

There are shushes. There is restraint. There are moments when the room locks in and everyone listens together, and those moments feel earned. The cold backs off. The song gets the space it deserves.

Tanner Usrey has had our favorite set of the festival so far. More words to come on that in the final wrap up. But his closer Fleetwood Mac cover with no less than 20 guest artists joining in is what this thing is all about.

Among the songwriters we’ve seen so far are Shelby Stone, John Fullbright, Bri Bagwell, Courtney Patton, Randy Rogers Band, Kaitlin Butts, Walt Wilkins, Jamie Lin Wilson, Josh Weathers, Silverada, Josh Grider, Drew Kennedy, Kashus Culpepper, Cross Canadian Ragwees, JD Graham, American Aquarium…and probably three more names I’ll remember tomorrow.

Sometimes they’re onstage. Sometimes they’re leaning against a wall listening like everyone else. Mile 0 doesn’t separate those things.

Graycie York, Julianna Rankin, and Taylor Hunnicutt are all here. No joint set, no headline moment…just moving through the same rooms, laughing, talking songs. A relationship that traces back to River Jam 2024 and keeps holding without needing to announce itself.

That’s how you know it’s real. That’s what Galleywinter has always been about. Connection and reconnecting with new and old friends down here each year remains the highlight. Above the music. It’s about the people.

Two and a half days in, the wind is still testing us, voices are getting gravelly, and the hoodie is pulling its weight. The bartender is still running the room. The waitress is still two steps ahead. Cuban coffee is still doing the work.

And we’ve got two full days left.

The music keeps showing up. The people keep making it count. Mile 0 is fully alive. Cold air, warm rooms, and stories that are already starting to stick.

We’re right in the middle of it.