Mar 26, 20209 min read

The Kentucky life of Blair Thomas Hess

Updated: Apr 6, 2020

Story by Lauryn Haas | Photos by Isaac Janssen

Author Blair Hess lives with her husband, Elliott Hess, and their daughter, Elliott, in their Frankfort, Kentucky, home.

Blair Hess, accidental expert on the state of Kentucky and real writer (although she struggles to identify with the term, as many of us do), has made things difficult for herself in her household.

She met her husband, Elliott Hess, in college at the Kentucky Kernel on a story assignment that took the two of them downtown to interview the homeless. She wrote the story, and he took the photos. They now have a curly blonde four-year-old girl, also named Elliott Hess.

In their home, it’s Blair versus Elliott Squared.

“We named our daughter Elliott because things aren’t confusing enough in my life. I call her Ella, and she is very quick to tell me that’s not her name, her name is Elliott,” Hess said. “They band together because they’ll be like ‘well we’re the Elliotts and you’re not.’ Look what I’ve done.”

But Blair and her daughter do have one important thing in common: they’re both born-and-bred Kentucky girls. Blair grew up in Lexington, her mother is from the Maysville area, and her father is from Western Kentucky. As Blair puts it, she has a very “Kentucky kind of family.”

“A lot of friends when I was growing up would go out of state to visit grandparents, but my whole everything was right here in Kentucky. And I used to really hate that. I used to be like… why can’t my grandparents be somewhere cool that we get to go travel and visit, but summers were spent in Western Kentucky on my grandparents’ farm… I just had a very Kentucky upbringing, very traditional,” Hess said.

Vacations in Disney World and at the beach came second to exploring her home state. Blair’s family took regular trips to Lincoln’s birthplace, Mammoth Cave and Cumberland Falls. Every year she went to the Trigg County Country Ham Festival to marvel at everything from the prized pigs to the Ms. Ham Hock competition to the sack the pig contests. An appreciation for all that Kentucky has to offer was instilled in her from a very young age.

Blair Thomas Hess' home decor reflects her Kentucky upbringing.

When it was time to head off to college, Blair followed in her mother’s footsteps and decided on Western Kentucky University. She spent a year in Bowling Green studying journalism, but she wasn’t getting the college experience she had hoped for. After some thought and a phone call with her parents, she decided to transfer back to Lexington and attend UK.

“I got to UK and I started, and I just loved it,” Hess said. “I loved every second of it. I wished I had gone here for six or seven years; I wish that I could keep going. I just loved every bit of it.”

Her interest in journalism stuck. Blair knew that she wanted to be a writer in some capacity for all her life. She said she always wanted to tell stories.

“Very early on, I told my mom I was going to be a novelist. That’s what I was going to do. And I used to write these ridiculous stories that didn’t make any sense and would never be real novels, but I used to write stories all the time… And then I think I realized at some point that maybe that wasn’t a real career. It’s a scary thing when you realize that,” Hess said.

As the way many great stories begin, one day Blair walked down to the basement of the Grehan Journalism Building and into the office of the Kentucky Kernel. Although she ended up majoring in agriculture communications, she never left the Kernel.

“I kind of walked in the door, and I was like ‘Can I write here? Are you guys looking for people?’ And they said the same thing then as they say now: always. And it completely changed my life,” Hess said. “I mean every part of it. There are so many things I learned there that I don’t think I would have ever learned, but it wasn’t about the writing, it was about how to ask questions, how to talk to people, how to tell stories, and being a part of a team that all cared about the same thing."

“I don’t think I had ever been in a place where everyone cared about and were just as passionate and weird about the same thing. And nobody else understood why you stayed up until midnight working on something that how many people read? Do people read that? It didn’t matter. And I don’t think I had ever seen that or felt that before the Kernel.”

Blair acquired bridesmaids, bylines and a boyfriend during her three years as a Kernelite. She met her literary agent, Alice, at the Kernel as well. When graduation came, she had the opportunity to move to Nashville for a job at a custom content company. At the time, in the middle of the recession, “a job was the greatest thing you could possibly get,” so she took her chance to explore what there was outside of Kentucky. Blair and Elliott started doing long distance, as he had a job in Lexington, and she discovered she would have to come up with ways to keep in touch with her loved ones. More specifically, her best friend and co-author of her books, Cameron M. Ludwick.

Blair and Ludwick met in middle school and remained close throughout high school and college. Ludwick, who works in book publishing, had always wanted to be a writer, too. She majored in English and got a job at UK after she graduated. The two dove into their separate post-grad lives, and in 2011, they planned to meet up somewhere between them to catch up. Ludwick mentioned she had never been to Mammoth Cave. Since Ludwick was born and raised in Kentucky just as Blair was, Blair couldn’t believe she had never been. It was decided, and they planned a trip to Cave City.

“We met on a Saturday morning. I drove from Nashville to Cave City and she drove from Lexington to Cave City, and we met and we did a tour of Mammoth Cave and we stayed in a wigwam village,” Blair said. “And unknown to us, this was the first My Old Kentucky Road Trip. We didn’t really know that’s what we were doing, we were just literally meeting in the middle of our two places and we were driving around, but that trip kind of opened our eyes to something that could evolve slowly.”

After their weekend, the pair joked about writing a travel guide to help people avoid making some of the same mistakes they made, one of them involving a moccasin shopping detour that ended up derailing their scheduled tour of the cave. A month later, they planned a similar weekend trip, but this time they were heading to Louisville for a late-night tour of haunted tuberculosis hospital Waverly Hills. The trend continued.

Blair and Ludwick had a friend named Matt who ran a music blog at the time. It was beyond MySpace or Facebook, and he was entering this new internet territory of online sponsorships where he actually made money from his posts. With this as inspiration and her work experience running the media for her company, Blair decided to start up a WordPress site.

Why not?

The name of the blog, My Old Kentucky Roadtrip, was somehow born between the two of them, and myoldkentuckyroadtrip.wordpress.com came to life with stream-of-consciousness style posts about Cave City, Waverly Place, and everywhere in between.

Blair was learning about search engine optimization at work, so she started incorporating keywords into her posts and linking to travel and ticket sites. One day, she ran an analytics report for a work website and decided to see how My Old Kentucky Road Trip was doing while she was at it. She found that their blog was getting 180 to 250 viewers daily without any promotion.

“Honestly, I wish I could tell you that there was this big grand plan, and we had all these great creative ideas, but we really kind of just were playing and making it up as we went along,” Blair said. “People were doing what we were doing, searching Cave City, Kentucky, in Google, and nobody writes about Cave City, Kentucky, so My Old Kentucky Road Trip was pinging up on top of the search engines. And then people would comment and that would drive it even higher and higher and higher.”

They decided to see what would happen if they strategized. They made a Twitter and a Facebook, and they started previewing places they were going to go before they went. The castle on Versailles Road was about to open as a bed and breakfast, and they posted about it on the blog. That post got picked up by bigger sites and went viral. Blair purchased their domain name for $18 and they dropped the .wordpress. It was getting serious. Until things got busy.

“I moved back to Lexington in 2012 and got married, and Cameron got a bigger job, and we stopped road-tripping, and we stopped updating the blog,” Blair said.

Because both her husband and daughter are named Elliott, Blair Thomas Hess says the family dynamic is often her versus "Elliott Squared."

Nine months passed. Blair logged into the blog’s Gmail account on a whim and found a message from a woman named Katie Perry with the History Press, now part of Arcadia Publishing. She was interested in doing a My Old Kentucky Road Trip book. Blair realized the opportunity may have passed, but she told Ludwick about it anyways, and she was thrilled. They decided they had to reach out.

“So, we called Katie Perry back and because we are the luckiest people in the entire universe, Katie Perry was the kindest person you’ve ever met, and she still wanted to do a book with us and she wanted us to take 25 road trips across the state, and she wanted us to take pictures and she wanted us to write about our experiences and she wanted us to publish a book,” Blair said.

They agreed. My Old Kentucky Road Trip made the transition from the web to print. The book deal was signed in 2014, and the first book came out in 2015.

“This was about the same time that Kentucky for Kentucky was establishing itself, and Kentucky was suddenly kicking ass… Those things were starting to kind of come about,” Blair said. “So, there was this surge of pride in the state. We didn’t want to be in the bottom five in education and obesity. We wanted to be more proud of where we were from.”

Blair said the feeling of holding your own published book is something that will never get old.

“I remember they sent us author advances, and I think I just held it forever. We went to dinner that night and I took it with me and I went to the store and I took it with me, I mean I carried it in my purse for a week. And it wasn’t even to show it off, I just wanted to have it close to me,” Blair said. “Every bookstore I walk in I look for it. Out of habit, I could be in Ontario, Canada, or Lexington, Kentucky, and I’ll look for it. Every time we walk in a bookstore, we move them to the front. Bookstore people probably hate us.”

They have since expanded the brand to include topic-specific books on Kentucky foods, bourbon, and Civil War historic sites. Blair has spoken on author panels and bourbon panels where she served as an expert on Kentucky, a role she said she will always exercise, whether a friend needs a restaurant recommendation or a panel needs a speaker. A publisher in Indiana asked Blair and Ludwick to do a similar series in their state, but they decided against it. It’s kind of a Kentucky thing.

But Blair does write about other places, too. For Christmas 2018, the Hess trio took a Euro-trip through England and France with Blair’s mother, her brother, and her brother’s husband, against plenty of discouragement on taking a two-year-old to a new continent with a five-hour time difference. But little Elliott is a traveler at heart. She turned three while on a train from Paris to London and took in sights that some people dream their whole lives of seeing, something that Blair said she will remember forever.

“It was the wildest thing. I remember we went to the Eiffel Tower and we did it at night, so you know how they light it up and it twinkles. We’re sitting in line waiting to get on the elevator to go to the top, and my mother is holding my daughter, and they’re watching this big huge Eiffel Tower twinkle, and I remember thinking, this is the most amazing thing you could watch,” Blair said. “And they’d never seen it before, and who knows if either of them will remember it in ten years, probably not, but I will remember it. And it was one of the most special things.”

For now, moments like these live exclusively in journals for Elliott to read when she gets older. But what’s next for Blair’s brand? Maybe My Old European Road Trip with co-editors Elliott Squared. We’ll have to wait and see.