Mile 0 Fest strolls into its third year of existence and the heaven on earth that many of us discovered in year one has only gotten better. That first year many of us stumbled into the Keys drunk on romantic notions of Buffett, Hemingway and with no internal compass of what to expect. Our wildest dreams were surpassed. We were the Lewis and Clark of Canada and Boland. Each of us on that maiden voyage from the organizers to the bands to the attendees broke ground on what could be possible with a festival. Traditions were started. Relationships designed. Memories created. Debauchery fuzzed. Music made. But, to think that one day this festival would be headlined by the likes of Jason Isbell and the 400 Unit and Robert Earl Keen is something I don’t think we could have imagined that first year. The coolest thing is that the organizers continue to maintain the boutique festival feel and balance of a mom and pop operation while keeping crowd sizes small and still bringing in the biggest names available.
We’ll cover the music up top of this article and toward the bottom you can find general musings, FAQs and thoughts on paradise.
With so many artists in so many places, it’s truly impossible to hit every show that you’d like to. We’ve been pretty lucky to make 99% of all the ones we’ve loved the last two years. But, this year the organizers ratcheted up the pressure by placing several must-sees simultaneously on the schedule. Our tip is to grab a drink and get ready to hit parts of multiple shows at once. You can make it from tip to tip of the island in 15 minutes on foot. 4 songs here, 3 songs there. You can see multiple favorites in small windows of time.
No show is bad, but below are the non-Amphitheater shows we’d recommend you popping in to see. As far as the Amp shows go, you know what you’re getting. A-list Americana/Texas/Red Dirt/rock n’ roll from the biggest names this type of music has to offer. Jason Isbell is as big (and good) as it gets. Add in the exciting up and comers like Shane Smith and the Saints, Mike and the Moonpies alongside scene stalwarts like Randy Rogers Band and Wade Bowen, throw in a dash of legends such as Robert Earl Keen and Cody Canada, top it off with Whiskey Myers and Lucero among all the other names and it begs the question…has a better lineup ever been assembled for this music? We don’t think it has. Looking forward to seeing that thought proven correct. Now…on to the side stage attractions!
Tue Jan 28
6:00pm – Kickoff Party on Duval Street – The Zyn Duval Street Stage
The Duval kick-off party featuring Shinyribs, Charley Crockett and The Steel Woods. We’ve known for over a decade that there ain’t no party like a Shinyribs party because a Shinyribs party don’t stop. Kevin Russell and the gang have ratcheted it up even further the past two years in Key West. A place made for the swamp funk grooves of the Ribs gang.
Wed Jan 29
12:00pm – Johnny Chops- The Marker Pool Party Stage
When not holding down the low-end for the Randy Rogers Band, Chops is a unique and entertaining songwriter. You’ll recognize some RRB deep tracks but you’ll walk away having learned so much more. Chops will be taking the reigns of the Galleywinter Instagram feed on Fri Jan 31!
1:20pm – Drew Kennedy – The Marker Pool Party Stage
Drew Kennedy has been one of the best songwriters in Texas for 15 years. It’s fantastic that he’s been added to the lineup this year and will be able to showcase his songs for new and old fans alike. If you’ve never seen him before, make sure you catch this set.
1:50pm – Garrett Bryan – The 1800 Tequila Southernmost Beach Resort and Cafe Stage
Garrett Bryan has grown alongside the festival. A wide eyed newcomer in 2018, 2020 finds GB as confident as ever. He’s yet to play a bad set in Key West…this won’t be the first.
1:50pm – Bri Bagwell – The Shiner Sunset Pier Stage
Bagwell is our IG Takeover artist on this date and she always delivers a standout show. Her energy and vibe always raise the setting she’s in up…and she’ll be starting from Sunset Pier. Should be special.
2:40pm – Bruce Robison and Kelly Willis – The Marker Pool Party Stage
The dean of modern Texas songwriting, Bruce Robison will be joined by his wife Kelly Willis as they parade through hits you’ve heard on the radio, covers and ones that they save for just when they’re on stage together.
2:40pm – Jason Eady – Hard Rock Cafe Listening Room
This will be an acoustic, listening room performance for Eady as he brings his unique take on honky-tonk music to you in its most pure form.
3:10pm – Walt and Tina Wilkins – The Shiner Sunset Pier Stage
Walt has long been referenced as a Reverend. A reverend of song, pride and humanity. When he’s joined by his beautiful bride Tina you are in for a religious musical experience.
This day is capped by a run of Flatland Cavalry, Shane Smith & the Saints, American Aquarium and Jason Isbell and the 400 Unit at the Truman Amphitheater. It doesn’t get much better than that anywhere. Add in the environs and it’s as good as it gets.
11:30pm – Jack Ingram – The Deep Eddy Smokin’ Tuna Stage
Few artists embody the vibe of Key West better than Jack. Last year I’m pretty sure he never changed clothes once. He stayed up drinking late every night, and brought the hardcore troubadour spirit to each set he participated in. He logged more miles on the island than Jamie Lin Wilson…and that’s hard to do. This is one of his only scheduled appearances, so it’s a must see.
11:30pm – RC Edwards and Jonny Burke – The Bacardi Durty Harry’s Stage
RC continues to plow forward in the wake of the Turnpike break and he’s joined by one of our favorite songwriters Jonny Burke. These two men have co-written with Evan Felker more than anyone and that’s the level of song you can expect to hear at Durty Harry’s.
Thu Jan 30
Early in this day, things are headlined by the Outlaw Country Cruise dropping in for a docking visit. Bri Bagwell and Mike and the Moonpies are meeting up with Elizabeth Cook for a pool party. It should get pretty wild.
12:30pm – Juliet McConkey – The 1800 Tequila Southernmost Beach Resort and Cafe Stage
Juliet is one of the most amazing young talents making waves in the scene at the moment. The Virginia native landed on our radar last year and performed at our River Jam event. Her songs are real and stick their claws into you in a good way. She is also our Instagram takeover artist of the day for the 30th.
1:50pm – John Baumann and Bryon White – The 1800 Tequila Southernmost Beach Resort and Cafe Stage
You won’t find a better songwriter than Baumann. Come catch him alongside former Damn Quail, White and hear songs you recognize and some you’ll leave wanting to buy.
1:50pm – Kaitlin Butts – The Shiner Sunset Pier Stage
Kaitlin continues to establish herself as one of the strongest writers and performers in the entire region. She’s been a big hit at each of the previous Mile 0’s and this year finds her at even greater heights.
2:00pm – James Steinle – Key West Theater
Austin’s Steinle makes honky-tonk music in the vein of Moonpies but with a completely original spin. He’ll be plying his trade in the warm and acoustically pleasing confines of the KW Theater.
3:00pm – Brent Cobb – The Deep Eddy Smokin’ Tuna Stage
Cousin to Dave, and close friend to Adam Hood, Cobb has toured with Willie Nelson and Chris Stapleton. He’s written hit songs for chart smashers and he’s written songs that made him an Americana favorite. Come hear them all at one of the best bars on the island. High special guest alert.
3:10 pm provides one of those big conundrums. Three amazing shows kicking off simultaneously at three different locations. American Aquarium will be rocking things full band style at Southernmost. Drew Kennedy, Josh Grider, Kelley Mickwee, Walt Wilkins and Tina Wilkins will be recreating the magic of their Red River Songs Fest at Key West Theater. Then you have Courtney Patton and Jason Eady rounding things out for this window at Sunset Pier. There’s no wrong choice. Pick one and enjoy!
The amphitheater shows for this night include Cody Canada, Whiskey Myers, Jamie Lin Wilson and Mike and the Moonpies. After that incredible run of sets calms down and the afterparty’s kick off, there are more tough decisions to be made.
11:30pm finds Flatland Cavalry at Durty Harry’s, Reckles Kelly at Smokin’ Tuna and Shane Smith & the Saints at Irish Kevin’s. Dive in to one or all, just make sure you keep the partying going until 12:50am.
12:50 am – Adam Hood – The Bacardi Durty Harry’s Stage
Our favorite Alabaman night caps us at Durty Harry’s. He’ll be helping us round that last leg of the marathon with one of the best catalogs of songs and stories anywhere in the world.
Fri Jan 31
1:20pm – Will Hoge – The Shiner Sunset Pier Stage
In the past we’ve compared Hoge’s style to Springsteen and that is still an accurate description. He’s as adept at ripping your heart out acoustically as he is jamming out with you E street style.
2:30pm – Jason Boland 20th Anniversay of Pearl Snaps – Key West Theater
Boland’s Lloyd Maines produced masterpiece turns 20 this year and to celebrate he’s kicking off a busy 2020 by looking back at the album with a performance of it at Mile 0.
2:30pm – Hayes Carll – The Shiner Sunset Pier Stage.
Carll put out one of the best records of his storied career in 2019 and his live performances have always been a time for his dry wit and humor to shine alongside the lyrics. Look for all of it here.
3:10pm – William Clark Green – The 1800 Tequila Southernmost Beach Resort and Cafe Stage
WCG’s Rolling Stones esque honky-tonk rock found a welcomed home at the inaugural Mile 0. He even jumped in the Shinyribs conga line. Two years later he returns ready to hit you where it hurts.
5:00pm – Robert Earl Keen – Key West Theater
Easily among those you would find on the Mt Rushmore of Texas Music, the godfather of Texas Music kicks off his Mile 0 performance schedule with a theater show.
Amp performances on this night include: Cory Morrow, Kevin Fowler, Jason Boland, Wade Bowen and Randy Rogers Band.
11:30pm -80’s Ladies Tribute -The Larceny Cowboy Bill’s Stage
Jamie Lin Wilson will be joined by the likes of Courtney Patton and Kaitlin Butts among others as they pay tribute to the songs of The Judds, Reba, Barbara Mandrell, KT Oslin and the like. Sure to be a raucous time!
Sat Feb 1
2:40pm – Kylie Rae Harris Tribute hosted by Walt and Tina Wilkins – Key West Theater
KRH’s passing was one of the most heartbreaking moments in the history of this music scene. Rev. Wilkins will lead this emotional remembrance of artist and song.
2:40pm – Topo Chico Cowboys – The Bacardi Durty Harry’s Stage
Drew Kennedy and Josh Grider’s acoustic duo will bring songs and anecdotes to keep you entertained during this afternoon matinee set.
3:10pm – John Fullbright – The 1800 Tequila Southernmost Beach Resort and Cafe Stage
Fullbright will bring a full band jam to the whitest sand and best backdrop imaginable.
Amp shows include: Micky and the Motorcars, WIlliam Clark Green, Reckless Kelly, Lucero and Robert Earl Keen.
11:30pm – Jamie Lin Jamboree – The Deep Eddy Smokin’ Tuna Stage
Jamie Lin Wilson hosts this rollicking free for all jam that’s the perfect way to wrap up a week in Key West.
11:30pm – Cory Morrow – The Bacardi Durty Harry’s Stage
Morrow has long been a steadfast entertainer and the Key West environment should set up for him to deliver one of his classic sermons on life, love and music. This legend is the perfect way to cap off your week.
The food, the places, the times, the recommendations and all the rest.
-Blue Heaven – Two words. Lobster omelette. Another two words. Banana bread. This joint gets crowded early and fast, and rightfully so. There is a trick to getting a table that we won’t spill here…but ask around.
-The first year’s MVP was Jamie Lin Wilson. She seemed to teleport between stages and venues and always be in like 4 places at once. Last year that honor went to Jack Ingram. He went hard and he went everywhere. It will be fun to see who takes the trophy this year.
-After two years of making the drive down 1, we’re flying in direct this year. But, there are pros and cons to both. Whichever route you take getting there, once you are there it really doesn’t matter what time it is or which direction you’re going…there will be live music and good times awaiting you.
-Don’t rent a scooter or golf cart unless you have children with you. Parking is expensive and hard to find. You can walk everywhere you need to go and it is free.
-Shiner is sponsoring the beer and bringing Prickly Pear with them.
-Better Than Sex – Terrible name. Amusing concept that takes itself too serious…but the delectables are undeniable. Campy waitresses read the sensual names of dressed up chocolate cake in an ambiance befitting a grocery store romance novel. But, the confections are damn tasty and worth a drop in.
-Mile 0 staff has clued us in to some cool innovations this year. We can’t spill them all but be watching the app and your inbox over the coming days. Also…four words: a/c in the port-a-johns.
-The past couple years the stage at Southernmost has been an acoustic one, this year it’s a full band extravaganza featuring sets from the likes of William Clark Green, American Aquarium and Shinyribs.
-There is plenty of time to take in tons of music and hit all the touristy, lazy, beach stuff you’d like. Key West is like no other place on earth. The pace is up to you, but the vibe is uber chill. Always.
-Later start times for the Amphitheater stage mean more music at the side stages, take advantage!
-Check the forecast. Despite the near perfect weather most of the the time, there were a few moments of chilly air last year. You’re going to be walking a lot, so pack more than flip flops. Probably leave the jeans and boots at home. This ain’t really the place for all that.
-The entire vibe of Duval is like a less rowdy Bourbon Street. That doesn’t mean any less fun. It’s still a damn good time, it’s just not as crowded and trashy (which has its place…love NOLA).
-Matthesen’s – We sampled a slice of Key Lime pie at just about every locale last year and found this place to be the winner.
-Hank’s has been added as a venue and they are paired with Garbo’s (which you may have seen on Diners, Drive-ins and Dives). The house that Hank’s is in was once owned by Robert Frost. Come get poetically torn up.
-Frita’s Cuban Burgers – A Cuban take on an American favorite. Just off Duval, this place is worth a stop on your Key West travels.
-To undertake a classic Key West experience, we encourage you to particpate in the Mile 0 Fishing Derby. Hit the waters the priates trolled but you’re not looking for booty, you’re looking for pounds.
-Caroline’s – Conch fritters are a Key West staple and we found none better than this place. A prime Duval location allows fantastic people watching while you imbibe.
-This year there is also a photo challenge sponsored by Key West 1st Legal Rum. Take part, win free booze. You’re already going to be taking tons of selfies and whatnot anyway…why not win some rum for your troubles?
-Hard Rock – We normally avoid corporate locations in favor of local in almost all scenarios. But, this place had the best mimosas and breakfast combo of any place not named Blue Heaven that we stumbled across last year.
-The app. It’s been updated and has some cool features like GSP enabling, photo frames and social media link-ups. You will also have the ability to leave reviews for individual shows. This helps the organizers know who you dug the most. So, if you see something you dig, especially on the undercard, let your voice be heard!
-El Siboney – Homemade sangria. Seafood.
-Sunset Pier – You’re going here for the views as much as the grub. Get there early to snag a primo table. We lucked into one last year just as the sun was going down. A true highlight of any Key West trip.
-DJ’s Clam Shack – Lobster rolls for days.
Smokin’ Tuna – Every bar in Key West is a fun one. But this has been our favorite two years running. Looking for a 3peat. There’s a bartender that looks like Chris Cornell who can spin it like nobody’s business and concocts the best cocktails known to man. It coincided with a set from Walt Wilkins and felt something akin to heaven.
-Find the Walgreens/CVS. Stock up. They’re open 24 hours and will be your best friend for any number of maladies both big and small.
-Hemingway House – come for the cats, stay for the stories.
-The Lighthouse – climb up to the top and take a look around the vistas of the beauty around you.
-The Conch Train – a silly tourist trap that we’re planning on doing an IG live tour of this year.
-Smathers Beach – best beach we found here last year. White sand, no rocks. Gets crowded.
-Mallory Square – a more laid back Jackson Square.