For Lexington resident Cooper, cycling is deeply connected to place.

He has lived across Kentucky, growing up in four different towns, including two in Eastern Kentucky, before settling in Lexington in the early 1990s. With family still in the western part of the state, his story stretches across regions, landscapes, and communities. Today, riding a bike has become one of the ways he experiences and reconnects with all of it.

“I always rode, but casually,” he says. “Mostly for commuting or social rides on my trusty and cheap 1976 Puch Free Spirit. I love that bike.”

It wasn’t until around 2018 that he decided to take cycling more seriously.

To test it out, he picked up a mid-tier steel road bike, a 2015 Raleigh, and set his sights on longer distances. His first attempt at a self-supported century ended early due to saddle pain, but something had clicked.

Finding a Rhythm

When the pandemic reshaped daily life, Cooper made a move that changed everything. He relocated closer to the Legacy Trail and committed to riding regularly.

“I decided then and there I was going to give road cycling a serious and dedicated go of it,” he says.

That momentum paused in late 2020 when he was diagnosed with a genetic heart condition.

“Not being able to ride was really tough mentally,” he recalls.

Four months later, he was cleared to return. He marked the moment by buying his first modern carbon endurance bike, a 2021 Fuji from a shop in Danville.

“That summer I rode my first century on my own.”

From there, cycling became central to his life. He logged thousands of miles each year and joined friends at some of Kentucky’s most iconic rides, including Horsey Hundred, Rock The Crater, Redbud Century, and Licking Valley Century Ride.

“I always had fun riding these and seeing some of the same folks at each event,” he says.

Setbacks and Determination

In August 2024, while riding his Free Spirit along the Town Branch Trail, Cooper was hit by a car at the intersection of Midland and 2nd.

He had the right of way. He was completely blindsided.

The crash left him with a severe Lisfranc fracture in his foot, requiring multiple surgeries and months of recovery. He found himself in and out of the ER more than once, navigating complications and starting physical therapy almost immediately.

“The same staff started to recognize me,” he says. “Which was not exactly the goal, haha.”

Still, he set a goal.

“I was determined to have an actual bike ride on New Year’s Day 2025.”

 

 

He made it happen. Alongside friends, he rode 25 miles. His legs were weak. His foot still hurt. But he was back.

Over the next few months, he committed fully to recovery. Daily rehab. Indoor rides on a Wahoo Kickr. Physical therapy sessions with what he calls “The Rachels,” his two PTs who helped him rebuild strength step by step.

Then, in May 2025, another crash.

While riding on the Legacy Trail, another cyclist crossed into his lane while passing, and they collided. Cooper went over the handlebars, hit his head, and broke his back in two places.

It was another ambulance ride. Another hospital stay. Another long recovery, this time in a neck brace worn day and night.

And still, he came back.

“I was determined for a third time to not let a medical setback prohibit me from riding my bike,” he says.

Why the Kentucky Cycling Challenge?

For Cooper, the Kentucky Cycling Challenge is not about racing.

“As a relatively new cyclist for my age and with my heart condition, I realized racing wasn’t for me,” he says. “So I chose to challenge myself with longer distances.”

What keeps him coming back is simple.

“I really enjoy the feeling of being out alone on the roads, or riding with friends, and just getting out there.”

And in Kentucky, there is no shortage of places to explore.

“We have so many beautiful places to ride. For me it’s equal parts recreation and therapy.”

 

Moments That Stick

One of Cooper’s favorite memories comes from Rock The Crater.

“It rained on me six different times,” he says. “Then at the top of one of the final climbs, the sun came out. It felt like it was timed by Mother Nature.”

But just as meaningful are the comeback rides.

That first New Year’s Day ride after foot surgery.

Completing a metric ride again.

Returning to events like the Red River Rally.

Looking ahead, he is even considering taking on the full weekend “triple crown” at the Horsey Hundred.

Each one marks something bigger than distance.

Not just returning, but progressing.

Lessons from the Road

Through years of riding and recovery, Cooper has learned to pace himself.

“Managing your gas tank is key,” he says. “Not every effort has to be 100%.”

He has also come to appreciate the details. Good equipment. Comfortable positioning. The conversations with friends after a long ride.

“It’s rewarding to talk with other riders about the ride once it’s done.”

At its core, cycling has become something deeply personal.

“It’s about having fun, being in my own world, and proving to myself that I can come back from multiple injuries and still ride.”

An Invitation to Ride

To anyone considering the Kentucky Cycling Challenge, Cooper’s message is simple.

“Do it.”

With a range of ride distances and strong support from organizers, the Challenge offers something for every rider.

This spring, as riders explore Kentucky’s roads, trails, and small towns, Cooper’s story is a reminder of what is possible.

Not because the path is easy, but because it is worth returning to.

And sometimes, the most meaningful rides are the ones that bring you back, again and again.