April 21, 2025 
They say it’s never too late to make good on your dreams, and for many American eventers, a run around a CCI5* Defender Kentucky Three Day course, taking place this week in Lexington (April 24-27) is the aspiration of a lifetime.
Whether it began during their Pony Clubber days or naturally evolved in their teen years (or later!), even the most talented rider needs the time to obtain, train, and condition a horse capable of competing at the top of eventing sport. Not to mention, of course, the mental fortitude it takes to support the dream when the going gets tough.
“It takes years to prepare these horses for the 5* level,” eventer Shannon Lilley, 45, said in an Instagram interview with World Equestrian Brands. Lilley will make her CCI5* Kentucky debut this week aboard Eindhoven Garette, entering three, CCI4*-L competitions in order to make sure he’d be ready.
“I think picking the right events for the horses [is] really important to develop them,” said Lilley, who placed in the top-10 with “Garrett” at each of the 4*-L events they competed. “I am hoping, since this is my first 5*, and the horse’s first 5*, that that will have paid off.”
But Shannon Lilley isn’t the only 40-something American rider making their 5* debut this week in Lexington. Here’s a look at three rookie hopefuls proving that 40+ is the perfect time to hit your riding prime.
Shannon Lilley
The road to Kentucky has been longer for Shannon Lilley than for most riders on the startlist, but not for a reason she could have ever predicted. After earning a team gold medal in the 2011 Pan American Games in Guadalajara, Mexico, Lilley was on top of the world. One year later, though, disaster struck when she ruptured a disc in her spine, causing her to lose sensation from the waist down.
After intensive surgery to help her regain feeling, Lilley was forced to sell her top horse and was told she’d never ride again. She spent the better part of the next decade proving her doctors wrong. A few years ago, she met the 11-year-old Selle Français gelding Eindhoven Garrett, a horse once again capable of bringing her to the top of the sport.
“It’s hard to train these horses for this level with all the galloping and jumping you have to do,” Lilley told World Equestrian Brands. “I think he is as good as he can be right now.”
Matthew Brown
This isn’t the first time Matthew Brown has jumped at the highest level of a Kentucky Three-Day event. But given that the last time was eight years ago or more—and before the event’s CCI5* designation—we’re adding the Pennsylvania-based rider, 48, to our list anyway.
After all, its been a long road to get here. Brown has written about the time he was told by a top American trainer that he’d never make it in the industry because his family didn’t have the money. And while he struggled with that for a time, he didn’t let it stop him—ultimately competing the CCI4* at Kentucky in 2017 and 2016 and being shortlisted both for the Pan American and Rio Olympic Games.
Now mounted on the 13-year-old Irish Sport Horse, Alderwood—who finished 5th last fall in the CCI4*-L at Morven Park—Brown is once again ready to shift his focus to the top of the sport. “Alderwood feels very ready for his 5* debut next week!” Brown wrote on Instagram. “Thank you to our entire support team, we truly could not do this without you.”
Mary Bess Davis
Given that Mary Bess Davis’s FEI veterinarian father took up the sport of eventing when he was 52, it makes perfect sense that Davis should achieve her dream of a Kentucky 5* run at 46. Though she grew up eventing in Pony Club and vaulted in high school—then took a break from horses during college—they were never quite out of her blood. Davis starting eventing again alongside her dad when he took the sport up in his 50s, and eventually, she moved back home to the family farm in Covington, Georgia.
There, Davis brought three horses up to the Advanced level; she was also named to the USEF Developing Rider List. Though she took time off again to raise her two sons, 10 years after her 4* debut, Davis is back at the top with the 11-year-old AES gelding Imperio Magic (aka “McColl”) with whom she’s earned two, U.S. top-10 CCI4*-L finishes in the last two years. And though she’s had three horses qualified for Kentucky in the past, this is the first time this working mom will finally get to accomplish her goal.
“I never gave up on the dream, but I’m also, sadly, very realistic. So [with McColl], I really just took it easy and enjoyed the journey,” Davis told Eventing Nation. “It’s been such a gift—I didn’t expect it.”
