By Laura Scaletti
Portraits by Kacy Brown
It was only a matter of time before Madison Stewart followed in her family’s footsteps and got involved with horses. “As long as I can remember, horses have been part of my life. When I was younger, my mom, Michelle Radley, had her own horse training business, so I was always at the barn and went to horses shows with her most weekends,” Madison said. “My grandfather did horses with my mom when she was younger and my great grandfather had a feed store in Fredericksburg, Virginia. Horses have always been part of my family in some type of way.”
With a built-in trainer in the family, Madison first rode at age 3. From that first ride until age 12, Madison rode with her mother, with some lessons at a local barn mixed in as well. “I really liked riding with my mom growing up, especially since I was at the barn with her anyway and got to know her clients. It was fun for me to do the group lessons and go to the shows with everyone,” she said. “I was lucky that my mom was a trainer; it gave me many chances to ride clients’ horses. Even if it was just walking a horse out after a lesson, it was always so much fun for me.”
When Madison was 4 years old, she got her first pony, Princess. “She was the same age as me, so we were both learning and growing together. Princess lived at our family friend Margot Wagner’s farm. I learned so much growing up around Margot’s farm,” Madison said.
Michelle took Madison to Margot’s as much as possible so she could hang out and ride with Princess. “Not only did Princess teach me a lot, but she would put up with anything. We learned how to do lead changes together and small jumps,” Madison said.
Aboard Princess, Madison made her horse showing debut in leadline. Eventually the duo started showing off the lead and moved up through the Short Stirrup division.
Virginia Traditions
As Madison moved up the ranks, she showed on the local circuit until she got a large pony that could compete in the regular Large Pony division at rated shows. “We did one local show and then my mom decided to take us to our first rated show. After a few rated shows with my mom, I started riding with Pam Baker and that’s when I started focusing on rated shows,” she said. Once she was riding with Pam, Madison qualified to compete at USEF Pony Finals.
Michelle wanted Madison to train with Pam because she had spent her adult years training with Pam and knew Madison could learn from being part of Pam’s legendary program. “I learned so much and I’m so thankful for all that Pam taught me,” Madison said. “One thing that was always super important to me was before walking into the ring, you needed to ‘walk the walk.’ It was something you’d hear Pam say every time before going into the ring and it always helped. She wanted you to make a plan and have a set track as you walked in to compete.”
Part of the plan they worked on was getting Madison into the Junior Hunter ring. In 2022, Madison got her first 3’6” Junior Hunter horse, Nightcap, known as Grant. “He is a horse that will always be special to me. When I got him, I’d only been riding horses for a couple of months and had never shown in the 3’6” ring before. Grant always took care of me. He was one of the best horses I’ve ever had,” she said. “Unfortunately, we had a short career together, but in the few months I showed him, he took me from walking into the 3’6” Junior ring for the first time to WCHR Year End Champion in our zone.”
The next year, Madison purchased another incredible Junior Hunter horse, Philadelphia Story. “It took me a while to figure him out, but once I did, it led us to great success. We’ve had multiple tricolors in the Junior Hunters,” she said.
While showing in Virginia, Sam Meadows at The Meadows Farm offered Madison her first catch ride in the hunter ring. “Later on, he had gotten a jumper and offered me the ride. I was so excited because that was something I always wanted to do. So, I started doing some small jumpers with him,” Madison said.
Growing up in Virginia Horse Country, Madison was able to enjoy and appreciate the cohesive group of competitors who traveled the Virginia horse show circuit. “One of my favorite things about showing in Virginia was that you get to know everyone. It was always nice going to shows every weekend knowing there would be familiar faces and other competitors I grew up with,” she said.
Move to Makoto
Although Madison loved showing close to home in Virginia with her lifelong friends, after her first experiences in the jumper and equitation rings she was ready to broaden her horizons. “I really wanted to experience different horse shows around the country,” she said.
After considering her options, Madison decided to begin training with Liz Reilly and Erica Quinn at Makoto Farm in Ocala, Florida, in 2024. At the time, Madison was leasing E Di Luca, who had previously been in the Makoto program. Knowing he had been successful with them previously helped her make the decision to move to Makoto.
“In the past year, Liz and Erica have helped me accomplish so many goals. With their help, I’ve competed at the North American Youth Championships, did my first International Hunter Derby and International Derby Finals, Gladstone Cup and my first Medal and Maclay finals,” she said.
Madison credits Makoto with giving her incredible opportunities to add to her equestrian resume. “Having the opportunity to show Small Kingdom has been one of my favorite parts of being part of Makoto. He has always been one of my favorites to watch with Augusta Iwasaki. So, now having the chance to show him and have him take me around my first International Derby and International Derby Finals has been amazing,” Madison said.
Showing Small Kingdom was a pinch-me moment for Madison, as she’s always looked up to Augusta. “I used to watch her when she was a Junior thinking what an amazing rider she is. Now that I’m riding with her mom, Liz, I’ve learned she’s not only a great rider, but she’s a great horsewoman, support system and friend,” Madison said. “Gus has given me confidence in my ability to ride and has supported me in so many ways as I’ve started in the jumpers and equitation. I’m so lucky my idol has become my friend.”
Balancing Act
Madison trains with Ocala-based Makoto, but she still lives in Virginia. To make this arrangement work, Madison is attending online high school through the University of Nebraska Online, where she’s a junior. “Online school has been great for me and is super flexible with my riding. I can schedule school around my showing and training times,” she said.
This flexibility enables Madison to travel all around the country to compete. “I travel most weeks with Makoto; usually my little sister comes to the shows with me and my mom comes on the weekends as much as possible,” she said. “I come home between shows to take breaks, and our horses come home to our Virginia farm after the circuits like Florida and Michigan.”
Madison’s currently focused on showing in the 3’6” Large Junior Hunters aboard Philadelphia Story and Lantos; 3’6” Small Junior Hunters with Small Kingdom; 3’6” Big Equitation on Gandalf and Medium Junior Jumpers on Serena. “I’ve been doing the hunters my whole life and have always loved it. I love derbies and galloping down to an oxer with a loop in the reins. Two years ago, I started doing the jumpers and quickly fell in love with it,” she said. “I’m newer to the equitation ring, but I feel like I’m learning a lot and doing equitation is helping me in the other rings.”
Part of why Madison is crazy about the jumper ring is her partner, Serena. “She’s been an amazing teacher to me this past year. We moved up from the 1.20m to the 1.30m before the end of the 2024 winter circuit and did the Pre-Junior team from Zone 3 at the 2024 NAYC. She takes great care of me and I know I can always count on her to get me around,” Madison said.
Before heading off to college in 2026, Madison has one big goal: do a Grand Prix at the Virginia Horse Center as a Junior. “It would be such a full-circle moment to finish my Junior career doing a Grand Prix at the same venue I showed ponies at for so many years,” she said.
While she’s hitting the books in college, Madison is looking forward to continuing her equestrian pursuits. “Riding has always been a huge part of my life and I think it would be pretty hard to stop riding or put it on hold while I’m at school. I really love the idea of riding on a team, being able to ride new and different horses and representing my school,” she said.
As she looks toward the future, Madison is thankful for her family’s support for her riding passion. “Their support has meant everything to me. They’ve encouraged me through challenges and celebrated my progress,” she said. “Knowing they are proud of me has been a constant source of motivation to push harder and achieve more.”
Follow Madison on Instagram @madisonnstewart._
Photos by Kacy Brown, kacybrownphotography.com
