Her patience and faith are rewarded when Ashbury jumps to a circuit title in Mississippi.

While Holly Shepherd was growing up in Mobile, Ala., Dennis Murphy warned her that if she wanted to ride seriously she would have to pack up and get out of town.

“He said I had to move somewhere not so far away from all the shows, but I wouldn’t do it. He also said that no one can focus on the hunters and the jumpers, that I’d have to pick one and stick with it, but I never could,” recalled Shepherd.

Shepherd ignored both pieces of advice and still managed to find a road to the top of the sport. As a case in point, she piloted Ashbury to the second year green circuit championship at the 2008 Gulf Coast Winter Series in Gulfport, Miss.

Shepherd carved out a niche for herself at her Grand Bay, Ala., Accolade Farm, attracting clients from across the state, as well as Nebraska, Florida, Louisiana and Maryland. Ashbury’s owner, Mary Walker, has been training with Shepherd for more than a decade, purchasing the gelding three years ago knowing he would need some time to grow into himself.

“When he started as a pre-green horse he had a little bit of what I like to call ‘first-jump-itis,’ ” said Shepherd. “His instinct was always to take a good look at the first fence, even as a first year horse.”

But last year’s five-week stay in Gulfport proved to be a turning point for the dark gray gelding. Over the circuit he grew more and more consistent in the professional ring as well as with his owner and her sister Ann aboard. The sisters take turns on the 8-year-old, with Mary contesting the amateur-owner divisions and Ann competing in the large juniors.

“He grows up more every time he walks in the ring,” said Shepherd. “He was a little bit of a late bloomer, but we knew at the start it would be a process to get him where he is. But he’s been easy enough for his owner to do right from the get-go.”

Unlike most professionals, Shepherd aims to spend equal time in the hunter and jumper rings, but last year she focused mainly on the hunters while her grand prix horse, Quilmes, sat out much of the season due to injury. But with Quilmes back in action and a few young prospects from Argentina ready for their first go on U.S. soil, Shepherd looks forward to getting back to the jumpers in Gulfport.

“Doing both is a lot harder than most people think, especially in terms of time consumption,” said the 39-year-old. “It takes an awful lot of time to get them winning in the hunter ring, more than to get a jumper winning.”

That determination has defined Shepherd’s career. She got off to an early start, making her first horse deal as a young child by trading her brother a record player for her first mount. She taught herself to ride down the streets of Mobile and to jump over pecan trees uprooted during Hurricane Frederick when she was 9.

“I said to my mom, ‘Do they make jumping horses?’ And she said, ‘Of course!’ ” recalled Shepherd. “I started jumping the trees—then later on I got a saddle.”

Shepherd’s parents leased her a barn and at 12 years old she started teaching lessons, while her father mucked stalls and her mother organized shows and clinics. As soon as she could drive, Shepherd headed out to San Diego, Calif., where she trained with Susie Hutchison and Jimmy Williams.

But the draw of her hometown pulled her back to the Mobile area. The possibility of an occasional hurricane has scared off most show stables from the southern part of the state, but that doesn’t faze Shepherd. She established Accolade Farm 15 miles inland, protecting it from the worst of the storms.

“For me, moving 45 horses at a moment’s notice is almost impossible,” said Shepherd. “We do the best we
can for them and hope for the best.

The horse industry kicks along down here. We showed in Louisiana during hurricanes for two weeks. It’s just how it goes: there might be a 40-minute delay, but you just deal with it.”

But when February rolls around, her location does provide one major advantage. Her 7-year-old son usually stays home when Shepherd hits the road, but with Grand Bay just an hour away from the Harrison County Equestrian Center in Gulfport, he can head to the show every weekend. That’s a big change from the rest of the year, when a dearth of big shows in the area means Shepherd spends eight to 16 hours in the truck to get to most competitions on her calendar.

“I’m not one to chase after points or go crazy for huge goals,” said Shepherd. “I really look forward to Devon [Pa.] and [the East Coast fall] indoors—and the kids, of course, are trying to qualify—but we try to pick shows we really like rather than those that get the most points.”

Between consignment horses and clients, Shepherd and assistant trainer Danny Grice will take upwards of 30 horses to Gulfport this year.

“Maybe if you’re from New Jersey or Wellington [Fla.] 30 horses in the barn isn’t much, but for someone from Alabama it’s a lot, between riding and training in the hunter, jumper and pony rings,” said Shepherd. “We’re busy—it slams. But I wouldn’t have it any other way.”