A Beginner’s Guide to Mile 0 Fest Key West

Words and Images by Laura Ray for Festy GoNuts.

The 8th Annual Mile 0 Fest Key West took place January 21-25, 2025 with headliners The Red Clay Strays, Randy Rogers Band, Shane Smith & The Saints, and Steve Earle. 

Each year after MLK Day, thousands of Red Dirt and Americana lovers converge upon the southernmost point of the United States for five days of music featuring more than 60 artists. What better place for a destination music festival than Key West?

Founded in 2018, the 8th Annual Mile 0 Fest Key West took place January 21-25, 2025 with headliners like The Red Clay Strays, Shane Smith & The Saints, and Steve Earle.

Mile 0 Fest offers a one-of-a-kind experience filled with incredible music, island vibes, and unforgettable moments. Read on to discover the highlights, insider tips, and the best of what this Key West festival has to offer! Starting with…

What is Red Dirt Music?

Americana music may no longer require a definition, but “Red Dirt” was a new one to this music fan. One Redditor describes it as “country music through grunge guitars.” According to our AI overlords, it is a genre of country music out of Oklahoma and Texas that blends Americana, folk, country, rock, honky-tonk, and bluegrass.

Mile 0 Fest Travel Tips

Planning a trip like this can be overwhelming. Here’s how to get to Key West, where to stay, and how to get around the island. Use these travel tips to make the most of your time down south of The South!

Getting There

There are many ways to arrive in Key West. Flying into Key West International Airport can be pricey, but is the most direct route. Alternatively, you could fly into a nearby airport such as Miami International Airport (MIA) and rent a car to take the scenic drive down the Overseas Highway, stopping to eat and shop along the way. Once you’ve crossed Seven Mile Bridge, you’ve made it into the lower keys. 

Another fun option is to fly into Southwest Florida International Airport in Fort Myers and take the Key West Express. This three-hour-long ferry ride is treated like a booze cruise. Hubs and I opted to fly into Key West and take the ferry back.

Where to Stay

Key West is insanely expensive, and the hotels are no exception. If you’ve got hotel points, this might be the time to cash them out! (Sorry loyal Holiday Inn Express customers, no IHG on the island.) Mile 0 Fest does sell pass packages that include accommodations, whether you are looking for a hotel, resort, guest house, or vacation rental. Opal Key Resort is a good choice since it is located near the main venue on the waterfront in Old Town.

We spent big bucks on a teeny tiny room at the Southernmost Beach Resort, which we love for its private beach access and proximity to our favorite lobster pizza. There were some shows on the stage at Southernmost, but most of the festivities took place on the other side of the island closer to the more touristy side of Duval and Mallory Square. It was kind of nice to be away from all the action, but it made for a pretty long bike ride! I’d probably go with one of the package properties next time for proximity and price.

Navigating Key West

Key West is only a mile wide, but that doesn’t mean you should get around on foot. Avoid shin splints and rent a bike, scooter, or golf cart. Having a car in Key West is just a nuisance since parking is practically nonexistent and pedestrians and bicyclists constantly dart in front of vehicles. Other transportation options include The Duval Loop (free public transit), The Venue Trolley, and rideshares. Hotels often rent bikes or Fury will deliver them to your hotel and pick them back up when you’re done. 

Overall Vibes

Mile 0 Fest gives festival-goers a chance to explore the island’s music venues and local flavor with a country-fried twist. It’s a unique blend of laid-back island life and rowdy, foot-stomping Americana, where palm trees and pedal steel guitars coexist in perfect harmony. Whether you’re soaking up the sounds from a waterfront bar or dancing under the amphitheater lights, there’s no denying that Mile 0 Fest delivers a festival experience like no other.

Venues

Although Key West offers tropical island vibes to chase away the winter blues, there aren’t a lot of beaches on the island. While there were some shows on the beach at Southernmost as I mentioned, most were at venues scattered around Duval or at the waterfront amphitheater mainstage. Attendees get to explore Key West hot spots such as the historic San Carlos Theater, Sunset Pier, and Margaritaville as they hop from stage to stage. All of the venues served drinks and some of them had food, too. I thoroughly enjoyed the tuna nachos at The Backyard Bar.

Local Flavor

Mile 0 has good festival food as festival food goes, but Key West fare is too good to resist. Here are some of my must-haves on the island: A cortadito from Cuban Coffee Queen and/or Ana’s Café (even though I don’t drink coffee anymore), lobster pizza at the Seaside Cafe at Southernmost Mansion (even though I’m allergic to dairy), and Mattheessen’s peanut butter cookie layered with chocolate and peanut butter fudge (I had two!). Of course, you can’t leave the island without having a slice of Key Lime pie! Try the one at Blue Heaven, a classic Key West eatery.

The Culture

Since Key West is such a small island, you’re likely to run into artists wherever you go. In fact, my favorite band Fruition hung out in the crowd to watch a set or two. And since there are so many shows spread out all over the place (sometimes simultaneously), you get a much more intimate experience than at a big festival that just rotates between mainstages. This may be one of the things that keep people coming back year after year. 

We were definitely in the minority as newbies, but everyone made us feel welcome. In fact, some Red Clay Strays fans asked if I wanted to move in front of them when they found out it was my first show. So sweet!

There weren’t a lot of kids running around at Mile 0 Fest, although all ages are welcome to attend. Animals, however, are not allowed inside the amphitheater. The demographic skewed a little older than your average music fest, which I attribute to the genre of music, the location in retiree land, and the fact that this trip ain’t cheap. 

Diamante was in from head to toe, with rhinestones bedazzling everything from hats to boots. Snakes were trending too on earrings and jackets. It is the year of the snake, after all. Fringe is having a moment as well, decorating jackets and bags. I laughed at a t-shirt that read “Oklahoma Sober.” The main “it” accessory to have at Mile 0 Fest though is a cap from one of the vendors, Uncle Bekah’s Inappropriate Trucker Hats, with a funny saying such as “Now accepting all drugs.” I got a pair of mermaid earrings from another vendor that had really cute stuff called Coco’s Monkey Key West.

The Music

With 60 bands spread across 14 stages over five days, you can bet there’s a lot going on. I was torn between seeing Hayes Carll, Tanner Usrey, or The White Buffalo, who were all on various stages at 3pm on Saturday while 49 Winchester played the mainstage. Luckily, most acts played twice, so if you missed the first show you still had another shot the next day. This is not an exhaustive list, but here are some of the standouts from what I caught!

American Aquarium

BJ Barham and the boys got the party started right headlining at the amphitheater on Tuesday with “Crier” off their latest album, ‘The Fear of Standing Still.’ Barham commented that this was their “seventh-straight Mile 0.” It doesn’t get more Americana than American Aquarium, with songs like “Cherokee Purple” that recall growing up as a kid in the country, drinking hose water and eating tomato and mayo sandwiches. 

“Tough times don’t last, tough folks do,” Barham sang as hubs and I pulled up to Sunset Pier the next day on our bright yellow bicycles. We passed by Barham’s wife and daughter in the audience as we sidled up to one rail-riding mama who was living her best life. Tanya, as I learned was her name, was dancing and singing and Facetiming to every deep cut Barham and the boys busted out, like 2012’s “Saturday Nights.” The dude standing next to me sparked my curiosity when he said that he once offered Barham 100 bucks to play some song, but he refused to play anything off the first two albums. Now I need to know why!

Darrell Scott 

Did you know that in addition to classics like Travis Tritt’s “It’s a Great Day to Be Alive,” Darrell Scott also wrote The Chicks’ “Long Time Gone”? I’d seen Scott last spring, seated several yards away at a small songwriters’ festival in the heart of Kentucky called Sleeping in the Woods. Of course I had to catch his set at the San Carlos. Plus, it was a chilly 57 degrees out, so I was happy to sit indoors.

Scott started his debut Mile 0 Fest appearance with “Miracle of Living,” from his 2003 album, ‘Theatre of the Unheard.’ The singer/songwriter/storyteller mentioned how he co-wrote songs with Guy Clark during his Cold Dog Soup era before treating us to a performance of one called “Out in the Parking Lot.” Scott and Clark took the mundane goings-on of a parking lot and expertly crafted them into something magical with lyricism and a melody. 

Scott said he left country music when Urban Cowboy came out and went the singer/songwriter route. “What makes it country is it has drinking in it,” he told the crowd. Scott hopped on the keys for a little while before wowing the crowd with more virtuosic guitar riffs. He closed the show with “Urge for Going,” a Joni Mitchell cover about the change of seasons. It is one of the tracks off his latest album, ‘The New Modern Hymns,’ which had been out of print but was recently re-released.

Steve Earle 

Not sure why, but Steve Earle played Earle-y with Reckless Kelly as his backing band and people were not happy about it. The 70-year-old was billed to headline at 9:30 pm, but instead went on a full timeslot early at 8 pm, causing some fans to miss the show completely. The festival was really good about updating everyone on schedule changes with push notifications, but somehow this one must’ve slid through the cracks. Really it was the Reckless Kelly fans who felt robbed. Regardless, Earle got through “Copperhead Road” and closed out the evening with “Harlem River Blues” as a beautiful dedication to his late son Justin Townes-Earle, whose birthday was in January. Although more music was promised, everyone left since it was cold and rainy and the headliner had already played. Thankfully Reckless Kelly fans had another chance to see them playing their own tunes on the beach the next day.

Bob Schneider 

I am new to the world of Bob Schneider, which makes sense since his tagline is “Bob Schneider is the best artist you’ve never heard of,” but my friend told me I needed to see him. I could see what she sees in the Austin heartthrob with songs like “The World Exploded Into Love” that spread smiles across middle-aged women’s faces throughout the bar. He looped his guitar and played keys, then looped the guitar and set a drum beat on the keyboard to rap about a Burger King in Rome. Between his harmonica and humor, he was giving some serious John Craigie vibes. On the murder-ballad aptly entitled “Murder” he sang “murder” in hilarious voices, with an evil laugh to boot. My face hurt from smiling. The captivating singer/songwriter had the whole Backyard Bar singing his 2009 hit “40 Dogs (Like Romeo and Juliet).”

Brent Cobb

The sun went on vacation just about when we did and the weather in Key West wasn’t very Key West-y. Of course we were counting ourselves lucky with people back home in Kentucky warding off single digits. However, I had packed for Florida, so when we went to see Brent Cobb at the waterfront amphitheater that Thursday evening, I put on just about all the clothes that I had brought. 

Cobb commented that he never claimed to be a singer, just a songwriter, but that people keep showing up to watch him sing. The 38-year-old troubadour has been at it since he was just a kid. We froze our asses off as he finished with a song he wrote when he was 16 that I did not catch the name of, which ended up number eight on the Texas music charts.

Shane Smith and the Saints 

As soon as “Hooked on a Feeling,” the dancing baby song from Ally McBeal, came on and Shane Smith and the Saints walked onstage, I knew I was going to like this Austin band. The fiddle player, Bennett Brown, wore overalls. Only. The lead guitarist is named Sunshine. What’s not to love?

They played “Feather in the Wind,” “Mountain Girl,” and “Dance the Night Away,” all with Shane Smith’s collar half tucked inside his shirt. Cody Canada from Cross Canadian Ragweed joined in for a song. Smith said Canada was part of what got him “wanting to write a song.” Later there was a tribute to the “Boys From Oklahoma” band followed by their first performance together in 15 years, which Canada described as a “love fest” in a video response to those who were upset that they paid for an upcoming reunion in Stillwater, OK.

Shane Smith and the Saints blew the crowd away with a performance of Levon Helm’s “Hurricane,” which they and The Band of Heathens have both recorded. Giant beach balls were hurled into the crowd, but blew away just about as quickly as they came. They also played “Coast,” an apt song for our location, which Smith said was one of the first demos that they shopped around to radio stations. Catch Shane Smith and the Saints this year touring behind their 2024 album ‘Northerner.’

The Red Clay Strays

Brandon Coleman, The Red Clay Strays’ super-tall frontman, took the stage Friday night after a badass set by The White Buffalo. The 28-year-old’s white suit and pompadour hairstyle made him look like a young, lanky Elvis. Although the winds at the amphitheater that night were as strong as they had been all week, Coleman’s Aquanetted hair did not blow in the breeze like everyone else’s. Even though it was a chilly night, 3,500 people packed in the amphitheater, reaching max capacity for this beloved band. It was the Mobile, Alabama band’s fourth time at Mile 0 Fest and first time headlining. They saved their hit song “Wondering Why” for the encore.

Fruition

I love Fruition so much I showed up to Margaritaville for their Mile 0 debut on Friday in blue and white pinstripe overalls to match the band’s train engineer gear. Tulsa native Johnny Mullenax was playing when I walked in. Michael Schembre was flailing around like an inflatable flailing tube man – I thought he was going to set his fiddle on fire during “Sitting on Top of the World.” Fruition introduced themselves to the festival with classics like “Above the Line” and “Boil Over,” hits like “Labor of Love” and “Mountain Annie,” and new songs like “Lonely Work” off their latest album, ‘How to Make Mistakes.’ When we left, the venue was at capacity for the next act, Tanner Usrey, a talented young man who we got to catch later at the Southernmost stage.

Fruition played both of my favorite songs on Sunset Pier the next day, “The Meaning” and my new favorite, “Saturday Night.” Key West is just about as far from Fruition’s native Portland as you can get in the States, and the crowd reflected that. Plus, there were like five other shows going on at the same time. They played their newest single, “Whole World of Trouble,” as well as “Hard to Make Money” as yachts glided past the pier. Fruition returns to Florida in March on the southeast leg of their ‘How to Make Mistakes’ tour.

Hayes & The Heathens

Hayes Carll and the Band of Heathens banded together to form a supergroup, and not just for the festival – Hayes & The Heathens put out a whole self-titled album. I knew we were in good hands when I saw that the keyboardist had an organ and two keyboards. I tried not to fangirl too hard with Fruition in the crowd with me as we rocked out to “Nobody Dies from Weed,” Ray Wylie’s “Drunken Poet’s Dream,” “Hurricane,” and “I’m Gonna Be (500 Miles).” Headliners, the Randy Rogers Band returned to the fest for the seventh time to close it out, but after five days of music, I was too pooped to stick around.

Tour Key West

Might as well see the sights while you’re in town. Mile 0 Fest partnered with local tourist outfits to offer activities such as fishing and boating, food and local history tours, and more. Tipsy Tikis offers a fun way to see a show from a floating bar. There’s also snorkeling North America’s only living coral reef, kayaking in the mangroves, celebrating the sunset at Mallory Square, exploring Duval, and more touristy stuff like Mile 0, Southernmost Point, The Kapok Tree, The Hemingway Home and Museum, and The Key West Butterfly and Nature Conservatory. Pin a day or two on either side of your trip so you don’t miss a thing!

How to Be a Mile 0 Fest Pro

This may have been my first rodeo, but I did learn some things along the way! Whether you’re a first-timer or a seasoned fest-goer, a little preparation goes a long way in making the most of your time in paradise. From traditions to tips, here’s everything you need to navigate Mile 0 Fest like a pro.

Festival Traditions

The festival unofficially kicks off on Tuesday with the Shitshow at Dante’s Key West Pool Bar & Restaurant, a sprawling outdoor bar right by the Key West Express port. Get there early if you want a beach chair! The only themed day was Freedom Friday, so bring your red, white, and blue. 

Tips

• Nap: Music starts before noon and goes until about midnight. Keep your Energizer Bunny battery going with a quick nap during the dinner break in between the afternoon and night shows. (This also allows for two drunks a day if that’s what you’re into.)
• Pack warm clothes: Layer up! It is chilly on the waterfront when the sun goes down, even on a warm day. I was glad I had my Fruition beanie, although I felt silly for packing it! 
• Download the Mile 0 Fest app: Show times overlap, so you have to plan your schedule. This is easy to do in the app, which has a ton of other handy info. Also, if the schedule changes due to weather or an act having to drop out, you’ll receive a push notification on your phone. 
• Instacart: Although there are convenience stores, there’s not much in the way of grocery stores on the island, and what there is can be pretty expensive. Save a trip and order Instacart to have some snacks, water, beer, and other necessities delivered upon your arrival. 
• Bring earplugs: This is a good idea for any show, but when they are trying to get sound through the whole outdoor amphitheater on a windy evening, it can get quite loud up by the stage. Bring concert earplugs and soft earplugs for sleep – roosters start crowing at like 3am.
• Chairs: For seating, you can BYO lightweight collapsible camping chair or rent a plastic fold-out chair at the amphitheater. We brought Helinox brand chairs that we barely used, so I’m not sure if it was worth toting them.
• Join the Facebook group: Join Mile 0 Fest Key West Fans for more insider tips, info, and resale tickets.

Experience Mile 0 Fest

By the time the festival ended on Saturday, looking back at American Aquarium’s set on Tuesday felt like a lifetime away. I had worn a bra, make-up, and contacts for more days in a row than I cared to (not that those things are required in Florida). Watching the sun go down over the water as we pulled away from the island on the Key West Express, I thanked my lucky stars that I got to spend the week watching live music in paradise. Maybe we’ll get to do it again someday!