When I heard about the Roostertail Music Festival this past winter, I started making my plans immediately. For the past several years, I have spent the beginning of July combining my two favorite things: road trips to new destinations and fantastic live music so I could meet up with friends, old and new, who get me and share my passion for the same. I’d never been to Madison, Indiana before, so I looked it up and I noticed a charming town nestled in a valley between rolling hills and the Ohio River. There are beautiful waterfalls and architecturally stunning old mansions that dot the visual landscape within the town’s borders. The historic downtown area, known as the Madison Historic Landmark District, is 133 blocks long and filled with shopping and dining, and one shop I want to visit as a music lover, Crawdaddy Music, even specializes in vintage instruments. In 2006, Madison was designated as the longest contiguous National Historic Landmark in the United States. Once I got a look at the road map, and decided my 9 hour route with fun stops along the way, I was hooked on this adventure…honestly, I was 100% in the minute I saw the line-up!

The Roostertail Music Festival is only in its second year. Let me repeat that, it’s SECOND year. In order to understand how such a fantastic line-up, where people are coming from all over the country to experience, landed in a small town in middle America, we need to take a quick look at the historical event it is connected to, and the visionaries who are making it happen. 

The Madison Regatta started in the early 1950’s. Thousands of people would convene upon the town to watch the boats race down the Ohio River at high speed. It is an annual event that highlights the fastest boats on the water, and the town is proud of its longstanding heritage. Over the years, however, attendance and interest had dwindled, and the event was in considerable debt, causing the committee to take a look at every aspect of the weekend.  

Matt Wells, a Madison native, music enthusiast and owner of his own sports and marketing entertainment agency helped make the move toward rebranding the event to highlight the race and adding music. The first time in 2017, Indiana staples Reverend Peyton’s Big Damn Band and Nick Dittmeir and the Sawdusters played on Saturday night. Event sales jumped, and the committee knew they were on to something, so they began work immediately on 2018’s music, expanding it to a full companion festival where the crowd could watch the boat races during the day, and enjoy some of the best music around at night.  Matt took over the marketing of the event and brought Brent Turner, also a Madison native and music enthusiast, to head up the music, and he expanded the festival to include 12 bands with the Turnpike Troubadours as headliners. This increased the bottom line for the event that was once in the red, but now becoming a profitable event for the town. The fan response was enormous and the Inaugural Roostertail Festival helped boost it’s attendance four-fold, from 2000 to 8000 in the span of one year!  

The extremely dedicated team of volunteers, led by Wells and Turner, has an insanely awesome plan for this year’s festival, and is the reason they expect 10,000 attendees to converge on the event. Marketing well beyond the borders of Indiana and neighboring states has helped music lovers like me discover this and make Madison, Indiana Regatta/Roostertail a destination trip. The price of one ticket for all of these bands and the killer boat race event, which I’ve never seen before, so I’m excited about that too… it is LESS than what I pay for ONE ticket to see ONE of the artists on the line-up. Roostertail self-identifies as alternative rock and independent country festival, but keeps the door open for all genres as long as the sound is good. That is fantastic, and that attitude will make this a successful event for years to come. 

This year’s lineup is outstanding, and I still can’t believe that tickets for the WHOLE thing are only $25 for the music and $40 for the combo music/race pass. Starting off on the 4th of July, The Famous Amy Noel band, Steamship and Nick Dittmeir and the Sawdusters, all local to Madison, will be opening for headliner The High Divers, an Americana band from Charleston, SC. Their latest album was produced by Sadler Vaden, a solo artist, former founding member of Leslie, lead guitarist of Drivin’ n’ Cryin’ and current member of Jason Isbell’s 400 Unit. They have a tight sound, and I can’t wait to dance and sing along with the crowd on the first night of the festival. Their song, “Weighing on My Mind,” has just the right amount of rock and chill, so check them out here.

thehighdivers.com

On July 5th, The Pass, Frederick the Younger and Little Stranger will open up the night for America’s Sweetheart, Jamie Lin Wilson, followed by one of the best honky-tonk bands around, Mike and the Moonpies. Texas’ own Jamie Lin Wilson is one of the powerhouse voices out there right now that you just cannot miss. Her album, Jumping Over Rocks, incorporates soulful ballads along with guitar driving up-tempo songs that hit you straight in the heart. I’ve seen her several times live, and her shows typically feature her own amazing music, such as, “Whistling Past the Graveyard,” and are punctuated by her stories that always make me laugh. She is an absolute gem! jamielinwilson.com

Mike and the Moonpies, another amazing Texas band, are coming off of their 8 day residence at The Dells, and are some of the most fun artists I have ever watched grace a honky tonk stage. I’ve seen them at a large amphitheater and small venue, and they bring it all to their audience every time. We’re all going to look good in neon on Friday night! themoonpies.com

On July 6th, the festival has seven bands on the line-up. Brent Mathis, 16 Bones and Edgar Red will kick off the afternoon, and then Lexington, Kentucky native Justin Wells will get the night started in the most rock and roll way possible. I’ve followed him for a while, and love his music, but I’m excited to see and hear him live for the first time on this stage. http://justinwellsmusic.com/tour  Following Justin, American Aquarium, from Raleigh, North Carolina, will kick it with BJ’s red guitar flying around the stage. I see them regularly, so I know this will be a fantastic showcase of some of my favorite songs! http://www.americanaquarium.com/ As if that wasn’t enough, Atlanta based Brent Cobb is next on the line up. Having just seen him in Denver, this artist truly knows how to capture an audience from the first strum of his guitar! His newest album, Providence Canyon, is solid.  brentcobbmusic.com

Closing down the festival is one of the absolute best bands out there right now, Whiskey Myers.  I cannot stress this enough. If you haven’t seen them, you should. If you haven’t listened to their albums, you should. They have been at the top of my list of live acts for a while, and I don’t miss a chance to see them if I have it. Their show at the Ogden Theater in Denver the week before they opened for the Rolling Stones in Chicago was one of the best I’ve ever attended, of any band. I am more than stoked to watch this Texas band burn it down in Madison!  whiskeymyers.com

So, there it is… the beginning of my Road Trip to Roostertail… all of the history and anticipation rolled up into one.  My bags are packed, and I’m looking forward to meeting up with my friends from Georgia, North Carolina, Iowa, Nebraska and Missouri… among others, who will discover Madison for the first time, and I’m predicting an awesome experience at the festival!  If you are still thinking of something to do over the 4th of July weekend, you should really think about your own road trip there! Thanks Matt and Brent- we can’t wait!  

madisonregatta.com/music-festival