Ashleigh Glorioso has won three consecutive ladies hunter side-saddle championships at the Pennsylvania National, and each victory came aboard the back of an off-the-track Thoroughbred. Her most recent winner, Epilogue, is 20 years old and was originally intended for her sister.

Glorioso, 27, started riding side-saddle 12 years ago and has become an avid proponent of the sport. She’s always encouraging other people to try it, including her sister, Amanda Ramey.

When Ramey first started riding Epilogue six years ago, she did the local hunters with the Thoroughbred gelding (Northern Spur—Shared Reflections, Pursuit). Glorioso suggested riding him aside.

“Most people don’t want to try it,” Glorioso said. “I started because I was doing 4-H at the time, and it just looked interesting. My old horse had done it previously. He was a really good teacher, so I just kept doing it. Amanda got into it after I started doing some more rated shows. She wasn’t as fond of it at first. It is different. It’s something you have to get used to, so we basically switched horses. I rode Epilogue, and she rode my horse because he was a bit easier.”

Epilogue’s racing name was Algezir. He was bred in Kentucky by Carolyn Friedburg, ran 29 times, and won a little over $70,000. He began his career racing on flat turf but switched to jump racing in 2006. He last raced in 2011, and the Pennsylvania National was his first major indoor show.

Ashleigh Glorioso said Epilogue can be a bit of a handful despite his age. Al Cook Photo

Glorioso achieved her 2018 win aboard another indoor rookie, a gelding named Southern Will. Southern Will (Will’s Way—Parade Charade, Dixieland Band) and Epilogue both had basic training astride before they came to Glorioso, but she got her 2017 mount, Turtle, straight from Laurel Park (Maryland).

“Turtle didn’t move very well, but he jumped good,” Glorioso said of the now 16-year-old gelding (Malibu Moon—Sea In Flash, Satan’s Flame). He raced 41 times under the name Flame In Moon before retiring in 2011. “He needed a lot of downtime because he raced for six years, so I probably didn’t put a side-saddle on him for years after I got him. We had to work out a lot of kinks with him, but he’s a great riding horse now.” 

Glorioso frequently works with green horses and Thoroughbreds. She trains and rides for a few clients near her home base in Burke, Virginia, but also owns AshGlo Equine Services LLC and specializes in providing Magna Wave therapy. 

“I like getting horses off the track because they’re broke, and they’ve been exposed to a lot,” she said. “Of course their reactions will be different based on the horse, but they’re generally versatile and tolerant as long as you tell them what you’re doing. I think more people are starting to do [side-saddle] on Thoroughbreds, partly because they’re becoming more popular. For me, I mostly work with Thoroughbreds anyway, so the side-saddle class is a chance to show at a bigger venue when I can’t compete with the warmbloods in the normal divisions.”

Glorioso rides astride most of the year and competes at hunter/jumper shows. She puts the specialty saddle on a few weeks before a big show to allow her and the horse’s muscles to get used to the weight and positioning again. 

“Side-saddle is something different to do with them,” she said. “I think the tradition is interesting; it’s ladylike. I just like the added elegance of being all dressed up and braided. I like getting young horses and green horses. I like the challenge. I get bored if I keep doing the same thing, so it’s good to switch it up.” 

For anyone interested in trying side-saddle, Glorioso suggested finding an experienced trainer to start, and she emphasized the importance of proper saddle fit. 

“Do your homework, but just go for it,” she said. “You won’t know if it’s your or your horse’s thing until you try it.”