The Road to Railbird: A Conversation With David Helmers and the Making of a Dream

With a phenomenal lineup of roots, bluegrass, folk, blues and rock artists, the inaugural Railbird Festival is sure to be a landmark event for Lexington and central Kentucky. A-list artists like The Raconteurs, Gary Clark, Jr., Hozier, Tyler Childers and Brandi Carlile will top the bill, while the stellar supporting acts will include living legends Mavis Staples and Robert Earl Keen and Lucinda Williams, and St. Paul and the Broken Bones along with an extensive list of local artists.

The Raconteurs Press Photo

Over a year in the making, Railbird is the brainchild of local businessman, entrepreneur and music lover David Helmers, who is partnering with nationally renowned AC Entertainment, producers of Bonnaroo and Forecastle, as well as city officials, local civic leaders and the Lexington Convention and Visitors Bureau (VisitLex). To be held August 10-11 on the grounds of historic Keeneland, one of the world’s most acclaimed racecourses and auction houses for prize thoroughbreds, the festival promises more than just music. The area’s rich culture, including bourbon, food and horses will be on full display.


We spoke recently to Helmers about the birth of Railbird, his hopes for his beloved town and its music scene and the blood sweat and tears that went into making dreams happen.

A native of The Bluegrass State, Helmers was born in Italy, where his father was a lawyer serving as an Army Reserve Judge Advocate (JAG), but was raised in western Kentucky, where most of his extended family lived for generations. The middle child of three boys, Helmers followed in his father’s footsteps, pursuing law after earning a JD degree at University of Kentucky in Lexington after an undergraduate degree from Rollins College in Winter Park, Florida.

David Helmers

As a litigator for over a decade, Helmers saw more than his share of conflict that proved exhausting after a while. A heart-to-heart conversation with his wife Anne led to the decision to embark on an epic yearlong journey around the world with their young son and daughter in tow.

Once back in Kentucky, Helmers reinvented himself as a business consultant and mediation specialist with David L. Helmers & Associates, LLC. He is also a partner in an angel investment firm that helps fund community-minded endeavors such as Kre8Now Makerspace, a workspace where entrepreneurs, artists, tradespeople, inventors and educators share ideas and equipment to make dreams reality.

A consultation gig with a young local entrepreneur who was producing local music festivals led him to invest in the now-defunct Moontower Music Festival which ran in Lexington from 2013 through 2017. It was around that time that the seeds for Railbird were planted.

The following is a conversation with Helmers about Railbird and what fans can expect from the inaugural event.

MFN: What makes Railbird a standout from other festivals in the region and in your area?

David: I think what makes this festival a standout is really the fact that is so married to the location, trying to distinguish it by connecting to what makes this region so unique and special. As festivals have kind of emerged throughout the United States, I think you distinguish yourself by being hyper-local and connecting to what’s available where you are.

We’re very fortunate that Lexington and central Kentucky have just a fascinating collection of subcultures here and industries that are not found anywhere else. So, when you look at the bourbon industry and the horse — the thoroughbred industry, they’re located right here for a reason, and it ties to our geography and the hills and the limestone on the water that is filtered through that limestone. We’re really taking advantage of what makes Lexington so special and creating a festival that organically rises out of the location.

Photo Courtesy of VisitLex

MFN: What excites you most about this festival?

David: Well, that’s hard to say. There’s a lot that’s exciting about it. I think it started with Keeneland opening their gates and allowing us to have a festival on their property. Keeneland is to horseracing, in my opinion, what Augusta National probably is to golf. It’s a beautiful campus with a limestone clubhouse and over 1,000 acres of surrounding land. It’s just a very special place, and it’s near and dear to the folks of central Kentucky and to equestrians from all over the world.

I’m a music fan who has lived in Lexington, Kentucky, for over 25 years, and I’ve traveled to festivals all over the country. I felt like it was time for Lexington to have a festival of their own – a signature niche festival that celebrated all the great things that we have in Lexington and central Kentucky. So, I went to the management at Keeneland and met with their chief operating officer and shared my idea and this vision to have a festival here. And to my surprise and delight, they were willing to entertain that idea. So, we started with the site, the very specific site. So that’s pretty exciting to me that we can have this at Keeneland.

And then once we had the green light to do that, the conversation evolved to how can we create a festival that reflects Lexington and central Kentucky that celebrates all the great stuff we have to offer here. So we’ve pieced it together with a great lineup. It is a music festival first and foremost, so we wanted a great lineup, and I think we have that. And then we’re showcasing our signature industries here, which are the thoroughbred and the bourbon industries.

Photo Courtesy of Keeneland

MFN: You worked on this festival for a long time, and you kept it under you hat for a long time. The germination for this, the idea of Railbird, how did that come about and when did that come about?

David: So, I was involved here in a festival we did here for several years, and I was involved in the last couple years of that called Moontower. It was very much a grassroots effort, a local festival. It was a great learning experience, and it ran its course. We reached the end of that. The last year we did that was in 2017. And as soon as that ended, August 2017, and I realized that Moontower had run its course, I had this idea in my head – what did I learn from that experience and how do we improve on that and create my dream festival for Lexington and central Kentucky. And that was on a larger scale, a true signature event for this part of the country and a destination festival that was going to attract people to this area and show off what we have to offer.

So that’s the ideology, the birth of Railbird. And I met with our local governments, our convention and visitors bureau, a group called Visit Lex, and their president was very supportive of the idea. Then that led to a conversation with Keeneland because I thought, if we’re going to have a festival here, what’s the best piece of property in this area to show off who and what we are.

So Keeneland was then open to that, and that began a long process of finding the best possible industry folks, production partners, to bring this idea to life. And we talked to lots of different folks. Ultimately AC Entertainment came and visited several times, and we more or less recruited them to come here and partner and produce this festival with us.


MFN: You’ve put together quite the team between the civic and business groups and AC Entertainment, who are pretty heavy-hitters. Was it hard convincing them to come on board?

David: They are heavy-hitters, and they have a great track record, if you look at who AC entertainment is, founded by Ashley Capps. I mean, he’s been in the business for more than 40 or more years, produced a thousand shows a year, and of course, founded Bonnaroo almost 20 years ago and several other festivals; High Water and Moon River come to mind.

I don’t think it was hard to convince them. I think there was a process of educating them about what’s unique about Lexington. And when they came here they saw what there was to offer – the unparalleled landscape, the distilleries all in proximity to here, the horse farms around Lexington, our great food scene here, and our proximity to the really most of the country. Over 50 percent of the United States is in within a day’s drive of Lexington where we intersect on these highways. So those are all selling point and factors.

But ultimately, when the folks at AC came to Lexington and tasted the bourbon, went on some horse farm tours, and visited the site at Keeneland, I think they saw the richness of the culture here. They saw the depth of what we have to offer, and they became very enthusiastic about creating a festival here. They have been just fantastic to work with and booking the lineup.

MFN: Who is responsible for curating the lineup? Who, and how did you choose the mix of artists?

David: That began with Keeneland and trying to create a lineup that was in tune with Keeneland and their brand. They’ve spent decades creating a hospitality atmosphere that is uniquely Keeneland. So we knew that, whatever lineup we put together, it had to be consistent with that. You know there are certain things that just aren’t necessarily going to fit with Keeneland and their aesthetic and what people are used to in going to Keeneland.

One the other hand, we wanted it to be brand new. So pushing the edge of the envelope a little bit and letting Keeneland let its hair down so to speak was also important. So we started with that idea. How can we create something that is complimentary to what people expect from Keeneland but also fresh?

Bryan Benson is the vice president for booking at AC Entertainment, and he’s fantastic at what he does. He’s very collaborative, and we basically worked together with him leading the charge and ultimately handling that process. But it was an ongoing conversation where no suggestion was unwelcome. And we just worked together and curated a lineup that I am super proud of, and he did a fantastic job.

Gary Clark, Jr. – Javier Ortiz

MFN: Who are you most excited and looking forward to seeing?

David: Wow! That’s tough to say. So, I was just is New Orleans, and I got to see Mavis Staples and Gary Clark, Jr., at the New Orleans Jazz and Heritage Festival, and both are amazing. So that’s super exciting for me know that that level of talent is going to be right here in our hometown.

I think Brandi Carlile is someone I haven’t seen. And I’ve seen a lot of music, but I can’t wait to see Brandi here. Amongst the headliners, all four are great.

Brandi Carlile. Photo by John Ferreira

Tyler Childers is a hometown boy who’s done well, and we’re real proud of him and the arc of where’s he’s gone. He’s got a brand new album coming out. He used to play backyard parties here and little honkytonks and restaurants in town, and to see him do so well is fantastic.

I feel goofy saying this, but it’s like picking among your children. There’s a lot of strength in the lineup, but the middle of the lineup here is so strong, in my opinion. You’ve got legendary artists like Mavis Staples and Robert Earl Keen and Lucinda Williams, who are classic artists.

Tyler Childers Devils Backbone Hoopla 2018
Tyler Childers Devils Backbone Hoopla 2018. Photo Credit: Jody Carbone

And then you’ve got folks like Billy Strings, who is phenomenal. He’s jaw-droppingly good. So, I can’t wait to see him. There are people who haven’t seen Billy yet, but I think they’re going to get a chance to.

It really is hard for me to pick. I think there’s a common thread that runs through the lineup from top to bottom, and it’s musicianship. There’s bluegrass music on here. There’s roots music on here. There’s soul music on here, and there’s some straight up rock & roll. But they’re all excellent musicians. I think from the top to the bottom of the lineup, you’re going to see great stuff. Anytime I go to a festival, the ideal experience is you go and you’re excited to see a certain act because they’re your favorite. And then you go, and if you’re lucky at a festival, you leave there, and you’ve picked up a couple new favorites. And I think we’re poised to introduce the audience to some new favorites.

Billy Strings-Photo by David Lee

MFN: What does the festival mean to Lexington and the region. If this is successful, what would it mean?

David: I think Lexington has not experienced a festival like this before. So I think obviously it’s going to be a really good time. But I think it has the potential to raise the profile of the city and the region overall.

We’ve had ticket purchasers coming from over 42 states. We’ve had people purchasing tickets from as far away as Australia. So I think I think we’re inviting people and the world to Lexington and central Kentucky to have a great time.

You know, the lure may be that Jack White and The Raconteurs are gonna be here, or Brandi Carlile is gonna be here, or Hozier, whose album has debuted at number one. But I think the upside or the next step to that is that they’re going to come here and realize, “Oh my gosh. What an amazing place. What a beautiful landscape and what great food and what hospitable people.” And they’re going to be introduced to the thoroughbred industry, and they’re going to be introduced to bourbon culture and hopefully really fall in love with that.

MFN: What do you love most about your city?

David: I think it’s the people who live here. That may sound a little corny. You do have these really unique, interesting aspects of Lexington that you don’t find anywhere else. You don’t find hundreds of horse farms anywhere else. This is the horse capital of the world. You don’t find the distilleries that you find here anywhere else.

Those aspects are all really neat, but you’ve got very interesting people who live here – very proud and very hospitable people. Because we have a lot here that’s great.

I grew up in western Kentucky. I left the state for a decade, and I came back here. I’ve been here 25 years, and I’ve raised our kids here. There’s just no place like it.

Photo Courtesy of Railbird

MFN: We talked a little bit about Moontower Music Festival. The music business is tough and pretty notorious for eating its own. What made you want to get involved in an industry that is often tumultuous, risky and a little bit crazy?

David: I think I just have a passion for music. I have a voracious appetite for reading about artists and music. I love to see artists doing what they do best. I’m still enamored with discovering new talent.

It started from the idea that I have a passion for live music. I think it brings people together, and I think it’s great for a community. What launched me into wanting to get involved in something as crazy and tumultuous as producing a festival is I viewed my experience at working at a grassroots level producing Moontower as music festival college. It was a very small group of people putting together this festival. For me that became educational in that I was doing everything from assisting in booking and production to marketing and artist hospitality and merchandise. So it was great in that respect.

It’s a difficult business. I was also financing the event largely so, if things didn’t go well, it was money out of my pocket, which was also an educational experience. So at the end of Moontower, where we did a lot of things right, we learned in the process. We did some things wrong. I had a good understanding of the potential for right here and also what the necessary ingredients are to create a successful event. And I think that was pulling together the right partners.

So, I left there in September of 2017 with this idea that if you wanted to do it and do it right here, the key is getting the right partners – getting the very best production partner you could. Getting the support of the city and the convention and visitors bureau and finding the ideal location within our city/county/region. What motivated me was really the challenge that I felt like, one: that we could do it, and two: there was so much here to take advantage of. And then it became a process of seeing if we could pull together all the necessary components to have this grade-A fantastic festival. Knock on wood: I feel like that’s what’s happening.

Moontower logo

MFN: Where do you see yourself going in the coming years? What are your hopes for Railbird and what are your hopes for yourself, your family and your community?

David: Ideally Railbird continues and grows. You know, I was at The New Orleans Jazz & Heritage Festival, and it was the 50th anniversary. Ideally Railbird becomes a red-letter day on the calendar for Lexington and central Kentucky and it goes on beyond me. I think there’s the potential for this to be a durable event. So that’s my goal for Railbird.

Personally I see my job as a producer as just being someone who is working to make that happen. Day to day, I just try to be available to solve problems and move things forward to set the stage. Like all festivals, Railbird will evolve over time. This is the first year of the event. We have a great lineup, and we have a great deal of activities and ancillary events that people are going to enjoy. We have horse farms tours. There are going to be bourbon tastings. There’s great food, and it’s family-friendly. We’re starting with a really solid foundation. So it’ll evolve and become its own thing. So my goal and hope is for it to blossom and become whatever it’s intended to become.

Anne and David Helmers with friends at JazzFest

In the meantime, I’m working with other folks locally to produce a series of shows and do some other one-off concerts that are here in town. We’ve got some venues that are underutilized. So that’s a lot of fun too to kind of add to the cultural calendar with other live music and events.

I’m in an interesting phase where I have one daughter who’s off to college and I have a son who just finished his junior year in high school, and he’ll become a senior. So my wife and I are soon to be empty-nesters. So, we’ll see how we fill our time. But a big part of it right now is helping Railbird emerge and become reality, because 18 to 20 months ago this was just a concept. It’s real, and that’s super exciting.

L to R: Anne, David, Laney and Lee Helmers

Tickets for Railbird can be purchased by clicking here. For more information on the festival, click on the links below.


Comments are closed.