Culture

Queen of the Road


The Heartland Anthems of Rising Country Star Hailey Whitters

Words BY DYLAN TUPPER RUPERT

Wildsam

Hailey at the Jones County Fair in Monticello, Iowa | Harper Smith

Updated

3 Dec 2025

AS THE UNOFFICIAL HONKY TONK poet laureate of the Midwest, Hailey Whitters honed her wit and wisdom in years on the road. Not only from miles touring as a singer-songwriter, but all the way back to childhood, her earliest sense memories forged across asphalt.

“My dad worked in construction my whole life growing up,” the Iowa native recalls. “Honestly, the smells of the road, like diesel and grease—those always remind me of riding in dad's truck.”

Memories of her own road-hours have a slightly different flavor: the pink-soap scent of truck stop bathrooms, grease stains on late-night pizza boxes, Diet Mountain Dew fueling graveyard-shift drives from Des Moines to Nashville with her band in tow.

“The road is like its own beast,” Whitters says. “Essentially, I'm traveling like a trucker is traveling. The truck stops start to feel like home after a while, and that scene starts to feel very normal and customary.”

HONESTLY, THE SMELLS OF THE ROAD, LIKE DIESEL AND GREASE, THOSE ALWAYS REMIND ME OF RIDING IN DAD'S TRUCK.

Whitters paid her dues in Nashville, penning hits for the likes of Little Big Town, Lori McKenna and Alan Jackson. But when she really broke through, it was on her own terms. She self-released her 2021 breakthrough album, The Dream, coming out the gate with well-crafted songs of dreams and disappointments, singing about being “12 years into a ten-year town” and hoping for luck to turn. Which it did, for Whitters, who soon toured with the likes of Luke Combs and John Pardi.

On her 2022 follow-up, Raised, Whitters leaned into her Iowan roots, churning Midwestern motifs of red gingham, corncobs and Carhartt into delightful country-fair camp. (Check out her first platinum radio hit, the lime-in-your-Corona-refreshing “Everything She Ain’t”.)

Now, on her latest album, Corn Queen, Whitters evokes the cookout, the tailgate, the summer night front porch after hours, cracked beers shared with the crickets and the stars.

With her signature winking wit and fierce advocacy of a nothin’-fancy good time, Whitters might be positioned just a bit off-center from most Top 40 country, but she shoots straight for the middle of the heartland. Discoveries from her travels infuse both her songwriting and how she and her crew roll on the road. At Char Bar, a storied dive in Columbus, Ohio, they found their own blue zone (blue curacao):

“Nobody was on their phones,” she says. “There were no TVs. The vibe was so great. We were like, ‘what is going on?’ And that's when we noticed everyone was all drinking these long-glass drinks. And then we learned it was a fish bowl.”

THE WILDSAM QUESTIONNAIRE

What’s one place you’ve never been?

I’ve never been to Asia!

Mountain, desert or sea?

Sea.

Gas station snack of choice?

Diet Mountain Dew & Flamin’ Hot Cheetos

Other highlights include: Boondocks, in Springfield, Illinois (“it’s just a roadside honky tonk that was always really fun”) and DanceMor Ballroom, in Whitters’ hometown of Shueyville, Iowa.

“There's only one bathroom in the entire place, and the first time we played there, we ran them out of beer and people started going across the street to another country bar and buying buckets of beer and coming back.”

Suffice it to say that Whitters has been observing the country all her life from the road, from dad’s work truck to her first solo van tours. These days, she’s upgraded to a tour bus, but her outlook remains fixed on forging ahead. It’s taken her years to break through to the heart of America, and now she has country music’s ear with grit, charm and songwriting that brings out the best of the place.

“Seeing America from the windshield—you know, driving down the highway—it's all so different,” she says. “But it's also so much the same in a lot of ways. You drive through places in California that can feel just as rural as Missouri. It is just really interesting the way that it all kind of works together. At this point, I've traveled to every state in the US. So in a way, just kind of being out there on those roads, it feels like home. I feel safe on it.”

With Whitters at the wheel, or on the stereo, you might find yourself remembering how good it can feel to be at home, anywhere you go.

Read more like this

Wildsam

On the Trail of the Exodusters

Wildsam

Why Keeneland Captures the Soul of Kentucky Horse Racing

Wildsam

M.L. Rio Interview