By Nina Fedrizzi

As the curtain closes on one winning partnership, California’s top pony rider is looking ahead to new mounts, new divisions, and a new set of challenges – and she’s meeting them all head-on.

On a cloudless morning in early November at the Desert International Horse Park in Thermal, California, the in-gate had stalled to a halt outside of Hunter Ring 2. Horse show staff tapped their fingers, checked their watches, and called again over the radio, eager for an update on the status of their last rider in the NHS Hamel Foundation Medal.

With multiple ponies showing that morning, Shiloh Roseboom had been held up in Hunter Ring 4. By the time she’d hurried over to Hunter 2 for her 3’3″ equitation round on Venice, patience was in short supply.

“Everybody was waiting for me,” says Shiloh, 12, who calmly reviewed her course plan and rode out into the ring. “Sometimes I feel pressure knowing I made people wait, including the judges. But, I just had to do the course the best I could. I keep re-watching it on video, because it went so well. There was a bending line in 8 strides, but I did 7, and the judge must have liked it.”

In fact, the judge pinned Shiloh and Venice first, an accolade that the young rider is particularly proud of. “Everybody was like, ‘Who is this kid we’ve been waiting for? Oh wait, it’s Shiloh she’s actually alright,’” Shiloh laughs.

Through no shortage of hard work, Shiloh Roseboom has already mastered a number of techniques that riders with three times her experience still struggle with. Chief among them is an age-old adage: Don’t let them see you sweat. It’s a lesson that will become all the more pertinent this season, as Shiloh continues her transition from successful pony rider into the ultra-competitive junior ranks.

“I usually tell myself, before I go in the ring for a big class, that it’s just another show, just another class,” she says. “Even if there’s a lot of people in there, I just go in, try my best and pretend no one else is there.”

A Heavenly Partnership

Equitation is still a relatively new discipline for the Corona, California-based rider, whose claim to fame thus far – and rightly so – has been in the pony ring. Aboard her 12-year-old Small pony, Heavenly Patch of Blue (named for a small blue patch in her right eye), Shiloh has earned numerous championships at venues including Capital Challenge, Pennsylvania National Horse Show, WEF, HITS Desert Horse Park and Blenheim. In December, “Anna” took home her biggest accolade to date: the USEF 2019 Small Pony Hunter National Championship.

“This was the year that it all came together for Shiloh and Anna on a national level. It’s everything – it’s the training, it’s the work, it’s the ponies. All the stars aligned and Shiloh really grew up as a rider,” says Shiloh’s mother, Shari Gold Roseboom, herself a successful amateur hunter/jumper rider.

“Remarkably, Horse of the Year wasn’t even our goal. It wasn’t on our radar, because as West Coast competitors, we’re so handicapped by the point structure, it’s not always realistic.” After realizing that Shiloh and Anna could be a contender after Indoors season, however, Shari says they decided to pursue the championship full-tilt.

“From Thermal to Vegas to L.A., then Florida, they had a tall order to go out there every weekend, knowing they needed to win everything. There was no room for 2nd place,” Shari says. “Every time they stepped into the ring, they won. Anna always came out exactly the same: willing, ready, and she always gave us her whole heart.

“The pressure was on Shiloh, but none of us ever said that to her. She just knew what was necessary to get over the finish line. The kid just has ice in her veins. I know there are moments when she’s been nervous, but it’s very rare. As a rider, she really manages that mental part of the sport very well.”

Paired together five years ago at nearly the same age – Shiloh was 7, Anna 8 – the winning partners have learned the ropes together, quickly progressing from the Short Stirrup division on up to the rated ponies.

“You just don’t find that very often,” says Christa Endicott, Shiloh’s trainer of more than two years. “I think Anna’s character is just really incredible. There’s not a lot of them that will tolerate what she does without being too green.”

“Shiloh has had so much success with Anna. I hesitate to say instant success, but it really has been,” Shari adds. “Chemistry-wise, they were a great fit from the start.”

For Shiloh, it’s a partnership that came together naturally, but grew with time: time in the show ring, time grinding it out in the lesson arena, and time doing the simple things together at home. “We know each other really well now,” she says, adding that she likes to cultivate her bond with Anna and her other ponies on weekends – bathing, grooming, and spending as much time with them as possible.

“Anna really trusts me, and I really trust her. Sometimes, I feel like I just have to think about what we need to do and she does it; like she knows what I’m thinking.”

Watch and Learn

Anna is just one of an ever-growing number of horses on the Roseboom string, which includes as many as four ponies, an equitation horse (Venice), and two junior hunters. Despite the family’s now-considerable dedication to the sport, Shari – who founded two businesses and grew up riding recreationally herself – says that owning a gaggle of horses and traveling the country chasing after national championships was not something that she initially envisioned. 

“In 2011, I got back into riding, and felt like I was getting the chance to do what I could never do as a child. But never in a million years did I think I’d be doing it at this level, with all these ponies and horses. It started very modestly and it just kind of grew,” she says, noting that Shiloh’s budding talent and dedication was a big reason for the shift. 

“Shiloh took her first lesson on her third birthday, and from then on, she would always come with me to the barn. When she was little, like five years old, she would come to the horse shows with me, and sit on the fence, and she just watched everybody – all the professionals, round after round after round.”

“Still to this day, Shiloh really wants to hang out, watch and talk about horses,” adds Shari, noting that at home, her daughter hones her education watching YouTube jumping rounds around the clock.

“It helps me to watch other people, usually professionals and more experienced riders, to learn how others do it,” Shiloh says. “When I was younger, I would always sit by the ring and watch John French and my old trainer Nick Haness ride. I like their style a lot. They’re soft and natural, and they make it look easy. They just come out of the turn and find the jumps. I feel like I ride a lot like that, with a soft hand, and helping the horses and ponies to relax.”

Shiloh’s trainer, Christa Endicott, agrees with that assessment. “Shiloh is very competitive, and really driven in that way. She’s got a great, natural, soft feel – a lot of things that you just can’t teach,” Christa says. But for Endicott, raw talent is just a starting place.

“Shiloh still has to work on her position and learn how to do things technically correct. I think that’s still very important for a naturally talented rider, to be effective on a horse’s back, and to manage your horse and get the most out of them.

“The amount of education and polish and Shiloh’s work ethic has really come a long way, as has her knowledge and understanding,” she says.

From Shiloh’s perspective, however, it hasn’t always been rainbows and butterflies. “Christa does not put up with lollygagging. It’s work, and when you get in the ring, you’re there to learn. You put in the work, you pay your dues and this is how you become a good rider,” says Shari, adding that Shiloh had a bit of a rude awakening when she took her first lesson with Endicott.

“Shiloh never had to work that hard in a lesson before, ever, and she did not enjoy it. She did not want to take her next lesson,” laughs Shari, who says that making students work without stirrups is one of Christa’s favorite pastimes. Fortunately, it’s also become one of Shiloh’s.

“In my lessons, we work a lot on the basics, like riding a good track on course. We work a lot with no stirrups, and I’ve jumped without them a few times over things like triple bars and barrels!” she says excitedly.

Adrenaline-seeking aside, Shiloh has also absorbed a number of more technical lessons from her trainer that are likely to serve her for the rest of her riding career. Says Christa, “Once Shiloh got to a certain point in her riding, I could start to explain to her how to get the best jump out of her pony, and how her riding really played a part in that. It isn’t just the pony’s job. That’s something that she and Anna learned together, which, of course, is a tool that Shiloh will really take with her.”

“Christa’s taught me the importance of good horsemanship and having a good attitude,” Shiloh adds. “She has taught me to always listen to the horses, because they can’t talk, but they always try to tell us something. She can understand what they need, and she tries to teach me those important life lessons.”

Movin’ On Up

In January at the Horse of the Year Gala, a beaming Shiloh took center stage to accept her giant, tri-color ribbon and a silver trophy reserved for the National Small Pony Hunter Champion. Though she still has big dreams in mind for her other ponies – foremost, a strong finish at Pony Finals 2020 with her bay Medium, Beach Boy – Shiloh and Anna will likely make their final competitive appearance together this spring at the Devon Horse Show. After that, Anna’s reins will pass to Shiloh’s little sister, Devin.

“That’s kind of going to be the end of an era,” Shari says. “I think the formal baton pass will happen after that, when Devin starts showing Anna this year. We’re getting her on her at home already to practice.”

Despite her middle-child status and some good-natured ribbing (“she’s a bit of a pot-stirrer!” Shari jokes), Shiloh has been happy to help Devin along with the transition, suggesting what spurs to wear with Anna and giving her flatwork pointers at home. But Shiloh will have more than enough on her plate this year to keep her occupied.

First on the list is making a name for herself in the equitation and junior hunters, where she’s already off to a successful start in the 3’3” divisions. Her plans are to move up to the 3’6” by Summer 2020. According to Shari, Shiloh’s intensity and steely character are likely to serve her well in the years to come, especially in the highly technical and occasionally cutthroat Big Eq divisions.

“Shiloh is strong-willed, independent and determined, but she actually has a very sensitive inner core. She has a big heart but she also has a tough exterior and very thick-skin,” Shari says.

“I am a strong, independent-minded woman so I’ve always believed it was important to instill those same qualities in my daughters. But it’s kind of a ‘be careful what you wish for situation,’ because Shiloh likes to challenge everything, and now that I have it, I’m ready to pull my hair out!”

Though she’s not ready to trade-in her jodhpurs and garter straps for a permanent pair of tall boots any time soon, it’s clear that Shiloh’s foundation in and out of the ring is more than solid. With poise, mental toughness, and a coach that prioritizes good horsemanship in her corner, there’s every reason to expect that Shiloh’s junior career will be just as successful as her pony years.

“For me, the transition wasn’t that difficult because I think you still need to be thinking about all the same things as you go around the show ring on a horse as you do on a pony. I still have to use leg, I still have to use my corners and keep my eyes up. I still have to listen to my horse (as I do with my ponies) and make adjustments as I go.

One thing that has definitely made my transition easier is my horse Venice. We were so lucky to get him, he is really a unicorn. He helped his previous owner go from ponies to horses and now he’s done the same for me. He’s so patient with me and he knows his job, so he’s helped “cover” for a lot of my mistakes while I’ve been learning. I could not have created a more perfect partner to help me learn the ropes,” said Shiloh.

She adds, “The horses are bigger with bigger strides which means the process of measuring where you are in lines is very different. On ponies, you often have to squeeze to make sure you get down the lines. But on horses if you squeeze too much you might get there too soon. So I’ve had to learn to be patient jumping in and then see where I am before I decided how I ride a certain line.”

“Riding teaches kids so much about compassion, and huge, huge, responsibility,” Shari reflects. “Christa has taught Shiloh a lot about listening to her pony or horse, and also being able to think on her feet.”

“She’s really taken Shiloh from a child rider to a more mature junior rider, and she’s given her a whole new set of ground rules and tools.”

Photos © Jayde Cole, Shawn McMillen Photography, The Book LLC, McCool Photography & Anasofia Vazquez