Mile 0 Fest turns 10: Cross Canadian Ragweed, Ryan Bingham and Old Crow lead Key West's Red Dirt week

Five days, January 26–30, 2027, at Truman Waterfront and around the island. Here's who to plan the trip around.

Mile 0 Fest returns Tuesday, Jan. 26 through Saturday, Jan. 30, 2027, and the 10th edition has one of the deepest Red Dirt and Texas-country lineups the festival has booked.

The evening headline shows are at the Truman Waterfront amphitheater. During the day, the festival spreads out across the island: the Key West Theater, waterfront stages, songwriter rooms, bars and pop-up sets. For the anniversary, organizers are adding The Reach Key West as a new daily waterfront venue. Passes and lodging packages went on sale in July through the festival's site. Single-day and three-day passes come later, once the daily schedule is announced.

Here's who to plan the trip around.

Cross Canadian Ragweed are the headline story. If you've been waiting to hear these songs on a waterfront stage, this is the year to go.

Ryan Bingham is one of the top-billed names. Give his night the same priority you'd give Ragweed's.

Old Crow Medicine Show bring a string-band set to a lineup that's mostly electric guitars.

Wyatt Flores is the younger headliner on the bill. Expect his crowd to skew younger and to know every word.

Kaitlin Butts is also billed as a headliner. Don't miss her set.

Behind that top tier, the middle of the bill is where Mile 0 is strongest. Wade Bowen, William Clark Green, Stoney LaRue, Kevin Fowler, Roger Creager and Micky & the Motorcars are Texas-scene regulars. Cody Canada & the Departed add a second set from Ragweed's frontman's other band. 49 Winchester and American Aquarium bring a harder edge, and Corb Lund comes down from Alberta.

The singer-songwriter rooms are worth your daytime hours. Jamie Lin Wilson, Courtney Patton, Adam Hood, Jason Eady, Drew Kennedy and Pony Bradshaw are all on the list. For acts to catch early, look for Tanner Usrey, Silverada, Taylor Hunnicutt, The Creekers, Nicholas Jamerson and Bri Bagwell.

The festival says more artists will be announced in the coming months, so expect the bill to grow before January.

A few notes for anyone deciding now. Lodging is the hard part in Key West in late January, which is why the festival sells hotel-and-wristband packages. If you're just coming down from the mainland for a night or two, wait for the daily schedule and single-day passes.

Ten years in, Mile 0 is the Red Dirt scene's winter week on the water.

Picture the last night: Saturday, Jan. 30, Truman Waterfront, the sun going down behind the stage. Plenty of people will have flown a thousand miles for that.

Sources: Mile 0 Fest — Lineup (mile0fest.com); Mile 0 Fest — Packages & Passes (mile0fest.com); Mile 0 Fest — Venues + Vendors (mile0fest.com); Mile 0 Fest — Contact Us (on-sale and pass release info) (mile0fest.com); JamBase — Mile 0 Fest celebrates 10th anniversary in 2027 (jambase.com); TicketNews — Mile 0 Fest unveils massive 10th anniversary lineup (ticketnews.com); Saving Country Music — Mile 0 Fest announces stacked 2027 lineup (savingcountrymusic.com); Key West Citizen — Mile 0 Fest Key West celebrates 10th festival (keysnews.com); Cody Canada - Wikipedia (en.wikipedia.org)