On the Road: A Visit to the Iconic Windy Hollow Dragway
My adventurous travels during early August proved largely enjoyable (despite toasty temperatures) as I visited a locale that’s been on my radar for quite a while. I spent a recent Saturday in the western Kentucky town of Owensboro, and while most of the town is somewhat rural, I soon realized that “small” it is certainly not. In fact, Owensboro is the county seat of Daviess County, and it’s the fourth most populous city in the entire Bluegrass State.
[Editor’s Note: This story originally appeared in DI #190, the State of Drag Issue, in September/ October of 2024.]
Owensboro has a number of claims to fame, and it’s even nicknamed the “BBQ Capital of the World.” A handful of well-known celebrities were born here, including NASCAR brothers Darrell and Michael Waltrip, as well as the often reclusive and immensely talented actor/singer, Johnny Depp. Occasionally, the internet will light up with excitement, since Depp still makes the occasional trek back to his birthplace.
Naturally, my favorite stop in all of Owensboro was its iconic dragstrip, known as Windy Hollow Dragway. I was eager to arrive early and sit down with Shawn Libs, who took over managing this legendary track a couple years ago, although his involvement goes back many decades. There’s a litany of twists and turns that have occurred in the life of this dragstrip, and Shawn was there for most of it. But before he came along, his dad, Francis Libs, was on hand for the absolute earliest days since he worked at the track when it first opened, and even operated the dragstrip for several years in the 1990s.
The beloved dragstrip we now know as Windy Hollow was first located on the south end of town on Veach Road and was originally called Owensboro Speedway when it was opened by Hal Miller in 1958. While many people have operated the track since that time, the Miller family has always retained ownership of the facility, as Mr. Miller’s daughter, Evelyn, now owns this historic raceway.
The Millers also own a dirt oval track that was built sometime around 1968. Shawn tells me that it’s his understanding that the family simply wanted the dragstrip and the oval track to be on the same property, so in 1971 the dragstrip was moved to its current location beside the speedway located on Windy Hollow Road.
Shawn was first brought to the track when he was just two years old, and by the time he was 14, he landed his first job at the dragstrip. “Back in those days we had hand-written E.T. cards, and I would drop them down a PVC pipe in the tower, and they would land downstairs in a wooden box,” he recalls.
It wasn’t long before Shawn was working the starting line, and he’ll never forget the day the track booked in a couple of jet cars. Shawn took cover behind a sturdy wooden board and clicked the tree to send them scorching down this rural eighth mile. Meanwhile, up in the tower, the windows were rattling so hard, the entire staff was huddled in fear under the counter! “To this day, that’s a great memory!” he laughs. Shawn has spent his fair share of time racing his own car here as well, and that’s what he enjoys the most.
The racing scene in rural Kentucky has changed over the years, and after 54 years of operation, Windy Hollow Dragway was shut down in 2012, and remained shuttered for close to a decade. In 2018, something extraordinary happened when the Westerfield family, who currently holds a lease on the property, began cleaning up the dragstrip, and they asked Shawn if he’d help them organize a no-prep race. He agreed, but admittedly had low expectations of any measurable success.
To his surprise, though, the event (which was supposed to begin at 2:00 p.m.) still had car haulers lined up along the road waiting to get in at 1:30 p.m. The third and fourth turns of the oval track had wall-to-wall spectators, with people standing on the bank anywhere they could to try to get a view of this event, which would prove to be a very pivotal moment in the track’s reopening a few years later.
“I totally underestimated the response we’d get from that initial no-prep race in 2018,” recalls Shawn. “It was arm drop, the whole nine yards. We didn’t have a Christmas tree, scoreboards, nothing…because it all left in 2012 when the track shut down.”
The wheels of determination began to turn toward reopening the track, and while the year 2020 was another pivotal moment in history, even the magnitude of disruptions caused by the pandemic still wasn’t enough to derail the reopening of Windy Hollow Dragway.
They currently have a bracket points program held multiple Saturdays per month with WDRA sanction, and also a Friday night trophy class (also with points) just launched this year, and it’s starting to gain traction.
Shawn was asked to be the manager shortly after the track reopened, and while he agreed, he says it’s only temporary, as the longing to be back on the track racing will always be his strongest desire.
In the short time it’s been reopened, a host of activities in addition to drag racing has been held here, including monster trucks and even midget wrestling, presented by the appropriately named “Dwarfanators” organization! To be fair, the wrestling spectacle was supposed to take place on the dirt oval track, but torrential rains made it too muddy, so the wrestling ring was moved to the dragstrip at the last minute. “It was actually pretty entertaining!” says Shawn. Currently, everything from a carnival to a huge concert is being discussed as possible entertainment ventures to be held at the dragstrip.
Regardless of what the promoters bring in, Shawn also treasures this hallowed property on non-race days. “This place is my playground,” he smiles. “It’s peaceful to come out here and think about what could be done, and it’s gratifying to make sure the front gate stays open, and knowing I play a part of that. I always want this place to remain open,” he concludes.
That’s a valid goal for certain, as many of these vintage dragstrips close and fade into distant memories. Windy Hollow Dragway represents the 165th track I’ve visited in my travels, and hopefully I’ll see many more before I’m through.
This story was originally published on October 17, 2024.
The post On the Road: A Visit to the Iconic Windy Hollow Dragway first appeared on Drag Illustrated.
