For Bailey Brown and other young equestrians in Tidewater, hanging out at the barn is better than a day at the beach. “I love starting my week off at the barn,” said Bailey, who rides at Roseoldian Farm in southeastern Virginia Beach.
The 12-year-old has been riding since she was six and knows firsthand the stamina and skill you need to stay in the saddle and the patience you need to guide and groom your horse. “It’s a sport, and you get a good physical workout,” she said. “Mentally, there can be ups and downs. You can be happy, upset, frustrated, and it all depends on how your riding is going. “Once we knocked over a jump,” she recalled, “but I always try to finish our courses strong and not be sad when I walk out of the arena. Patience will make you a happier rider.”
Let’s meet a few local riders and learn more about life in the saddle.
Building Strength and Balance is Key
Says Ava Miller, Rider at Horse & Hound Farm

Riding a horse at a fair was all it took for Ava Miller to know she wanted to take lessons. “I like riding bareback a lot,” said Ava, 9, who started lessons three years ago at Horse & Hound in Hampton. “I like riding English style because it’s easier. And I think barrel racing is really cool to watch. Maybe I will try that someday.”
Ava has learned that patience matters, especially when dealing with certain horses—like Sierra, who can be sassy and stubborn and nice, sometimes all in the same day.
When Sierra decides to be stubborn, she doesn’t respond to commands like she should, Ava explains. For example, Ava’s leg movements or her sitting position tells the mare what Ava wants her to do. On an off day, Sierra may just ignore those signals.
“Sometimes, she even looks like she’s shaking her head like ‘No, I don’t want to,’ when it’s time to canter or jump,” said Ava. If Sierra is not in the mood to work, she may be hard to catch in the paddock when it’s time for a lesson. Other times, the horse may trot when she’s supposed to walk.
“She can be very moody some days,” Ava said.
Other days, riding Sierra is like a walk in the park—just Ava and her horse in tune together. Ava particularly likes those times because her mind can wander a bit. “When I ride, I think about butterflies flying by,” she said. “I also think about holding on tight, so I don’t fall off!”
“One time after a jump, when I was riding a horse named Loki, I made a little noise and it startled him, so he took off,” she recalled. “I had to hold on for dear life until I could find a place to fall that wasn’t going to hurt so bad. It hurt really bad, but I got back on and finished my lesson.”
For now, Ava rides only at Horse & Hound, but eventually she wants to explore trail riding. Riding horses with different personalities at the farm and doing yoga to build better strength and balance are important parts of her learning curve, she said.
“I want to ride for a long time because horses inspire me,” she said. “They are pretty and very smart.”
It’s Important To Listen To Your Horse
Says Gwyneth Hudson, Rider at Bridlewood Farm

Crazy as it sounds, the thought of flying over hurdles with a 1,200-pound animal always appealed to Gwyneth Hudson. “I wanted nothing more than to try it for myself,” she said.
Four years ago, Gwyneth, now 13, started lessons at Bridlewood Farm in Chesapeake, where she rides English saddle and jumps. She lives on Knotts Island at the North Carolina/Virginia line, only about 10 minutes from the stable. Gwyneth’s steed is Glimmer, a 16-year-old Appaloosa, an American breed known for its colorful spotted-coat pattern. “She has to be one of the best ponies I’ve met or ever ridden,” Gwyneth said.
“She has her moments where she can be strongly opinionated and she definitely challenges me, but that’s why I love her,” Gwyneth said. “She has helped me become a better person and a better rider.”
Glimmer and Gwyneth have learned to work together by building trust and learning to respect and listen to each other. Working with a horse day in, day out helps a rider understand what a horse likes and dislikes, as well as the important dos and don’ts of riding.
Gwyneth recalled her “elbows in, elbows out” story as an example. “When I was first learning to canter, I would flap my elbows. It was just an instinct,” she said. “All the other lesson horses dealt with it but not Glimmer. She stuck her head down and stopped, and I flew right off. I learned if you want to stay on the horse, you keep your elbows in.”
Riding a horse is not like riding a bike or riding in a car, Gwyneth likes to tell people who have never been on a horse. It’s a partnership between you and the horse, she said, and you learn to listen to and know your horse.
In addition to keeping Gwyneth physically fit, Glimmer and riding have helped her cope during the pandemic the past two years. “Mentally and emotionally, riding is one of the only things that have kept me sane and well,” she said.
“Riding instantly relieves me of all my stress,” she continued. “The second I step foot on the farm, all the worries, concerns, stress, and the pressure of feeling like I have to be perfect just sort of melt away.”
Gwyneth says being around horses and the “amazing people” she meets at the farm makes her whole. “I don’t even want to imagine life without horses,” she said.
Riding and Jumping Take Total Concentration
Says Bailey Brown, Rider at Roseoldian Farm

While Bailey Brown looks forward to barn days, competitions are where she and her horse really shine. Recently she started competing in hunter-jumper events and loves it.
Two years of hard work and membership in the Virginia Beach Horse Show Association have paid off. She and Daisy, a Welsh pony owned by Roseoldian Farm, went to state finals and came back champions in her age group and in pleasure pony and short stirrup hunter divisions. Bailey now has her own horse, Sofie, a thoroughbred cross who also jumps.
Riding and jumping take total concentration, and Bailey is willing to do the hard work to get to that next level of awards. “I don’t see myself going pro; however, I plan to continue to horseshow for a long time,” she said.
“The events that I want to compete in as a junior are usually held in other states like Kentucky, Pennsylvania, and big horse arenas,” she said. “My horse and I have to learn to jump higher, and it takes a lot more effort from the horse and rider to accomplish that goal.”
Six years ago, Bailey knew nothing about riding. She started out on a lunge line, a long rope attached to the horse that the instructor holds and controls while teaching you to ride the horse in circles. During those sessions, she would hold her arms and hands out, putting them on top of her helmet and hips to learn balance without pressing her hands on the horse’s neck.
Then, she learned to walk, trot, canter, and eventually jump her horse. “My horse and I have had challenges, but I just practice patience knowing we can work through anything,” she said. “We kind of always just click.”