Dierks Bentley isn't your typical Nashville machine. While most country stars spend their lives climbing the ladder and never looking down, Dierks has a habit of jumping off the ladder entirely just to see what the view looks like from the ground. Or, more accurately, from the mountains.
People always ask about Dierks Bentley and family—specifically, how they managed to disappear to Colorado for a year and whether they ever actually came back to the "real world."
It’s a wild story.
Most people know him for hits like "Drunk on a Plane" or "What Was I Thinkin'," but if you talk to him for five minutes, he’s more likely to talk about his kids' hockey schedules or his wife Cassidy's marathon times than his latest number-one single.
The Childhood Sweetheart Reality
There’s no fake Hollywood romance here. Dierks and his wife, Cassidy Black, have been a thing since they were in the eighth grade in Arizona. Think about that for a second. Most of us can barely remember our eighth-grade lockers, but Dierks was already writing love letters to the girl he’d eventually marry.
They didn’t just stay together the whole time, though. Life got in the way.
He moved to Nashville at 19 to chase the dream. She was living her own life. It took until 2005—when Cassidy walked onto his tour bus in Las Vegas—for everything to click. They didn't wait around once it did. They eloped in Mexico the very next morning.
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Since then, it’s been a whirlwind. They have three kids now: Evalyn "Evie" Day, Jordan Catherine, and Knox.
Honestly, the way they handle their marriage is pretty refreshing. Recently, Dierks made headlines for admitting on the BobbyCast podcast that he and Cassidy actually sleep in separate bedrooms in their Nashville home. Before you start thinking about divorce rumors, it’s the opposite. He’s a notorious snorer and a light sleeper; she’s an elite runner who needs her rest.
They prioritized their health and their relationship over "traditional" expectations. It's that kind of blunt honesty that makes them stand out in a town full of curated images.
Raising Kids Who Don't Care About Fame
The Dierks Bentley and family dynamic changed forever in March 2020. Like everyone else, they went on a spring break trip to Colorado. Unlike everyone else, they just... stayed.
For a year, the Bentley family lived in a "box canyon" in Telluride.
Dierks has been open about how that year saved him. He was a "road warrior" who had been touring for nearly 20 years straight. Suddenly, he was just a dad in a 1994 Chevy pickup. No glitz. No Grand Ole Opry. Just hiking, skiing, and teaching his kids how to skateboard.
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Meet the Bentley Crew
The kids are growing up fast. In 2026, the ages look a bit different than the old Wikipedia entries you'll find.
- Evie (Evalyn): The oldest. She’s 17 now and a total powerhouse. She’s the one most likely to follow in her dad’s footsteps, though she’s more of a theater and powerhouse vocal girl. She’s even performed the National Anthem at major games.
- Jordan: The middle child, now 15. She’s the creative soul. While she dabbled in the fiddle, she eventually moved toward musical theater—something Dierks admits he knows absolutely nothing about, which makes for some funny parenting moments.
- Knox: The youngest at 12. If you see Dierks at a rink, he’s there for Knox. The kid is obsessed with hockey. Dierks, being from Arizona, jokingly says he’s useless at helping him with hockey skills, but he’s there for every game.
The Move Back to Tennessee
Eventually, the mountains weren't enough. Nashville is home because music is there.
The family moved back to Nashville full-time a while back, but they didn't leave their Colorado souls behind. They still keep a place out West. Dierks often talks about how he "manifested" that time away because he was so burnt out.
Living in Nashville again means a return to the industry, but with boundaries. You won't see his kids on a reality show. You won't see them being pushed into the spotlight unless they're literally dragging their dad onto the stage to sing with them.
What Most People Get Wrong
The biggest misconception is that the Bentley family lives some high-gloss, shielded life.
They don't.
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Dierks is often spotted at local Nashville spots, looking like any other tired dad in a ball cap. He’s vocal about wanting his kids to be "conscious of the environment" and to "serve in some way." It’s not about the money; it’s about the legacy of being a decent human.
The "Gravel & Gold" era of his career is really a reflection of this. It’s about the grit (gravel) and the reward (gold). He’s found a way to balance being a country superstar with being the guy who makes sure the trash is taken out and the hockey bag is packed.
Actionable Takeaways for Fans
If you're following the Dierks Bentley and family journey, here is how you can actually apply their philosophy to your own life:
- Prioritize Sleep Over Tradition: If separate rooms or different schedules save your relationship, do it. The Bentleys did, and they've been married over 20 years.
- Take the "Spring Break": You might not be able to move to Colorado for a year, but the value of unplugging from your "grind" to reconnect with your kids is immeasurable.
- Support the Pivot: Dierks doesn't force his kids into country music. He supports the theater and the hockey, even if he doesn't "get" it. Being a fan of your kids' interests—even if you're a stranger to the hobby—is peak parenting.
Dierks Bentley is still touring, still making music, and still one of the most respected names in the business. But if you ask him, his greatest achievement isn't the 15+ Grammy nominations. It's the fact that his kids still want to go camping with him in an old truck.
That’s the real story.