A Driving Force

By Jane Carlton

Not many 10-year-olds can say they’ve chased world champion combined driver Chester Weber around professionalgrade obstacles. But then again, most kids aren’t like Riley Wiltison.

Riley, now 11, has racked up ribbons in combined driving events up and down the East Coast. “He started out riding and he just wasn’t really into it,” says Riley’s mother, Billie. “He liked it, and he still likes to go for a trail ride, but [it was] nothing like driving. He’s very passionate about it.” Santa Claus was a bit overenthusiastic and bought Riley a pony when he was only two months old. “It was a little premature, but I’d always wanted a pony,” Billie laughs. “He trail rode her, did some local 4-H shows, the local fair, and that kind of thing. He liked it, but if he missed a show, he didn’t care. It was kind of take it or leave it.”

That’s where the Wiltisons’ Oakland, MD, neighbor, longtime trainer Cynthia Doll, came in. Riley had been riding with Cynthia for a while when one of her ponies, Doll House Shananigan, came back from lease. When Riley learned that “Shannon’s” previous driver was also young, the gears started turning. “Riley asked Cynthia if he could drive Shannon” she says. “When he came home, we thought, ‘We might be in trouble.’ He was so excited. He’d never had that sort of excitement about anything.” The sport couldn’t be more perfect for Riley. “It combines my two favorite things: going fast and ponies!” he says.

In the barn, Doll says Riley is extremely enthusiastic, attentive, and self-motivated. “He sees something that needs to be worked on, and he goes and gets it done,” she says. “If a horse needs a blanket straightened out or a stall’s not picked right, he’ll get out and fix it. You don’t have to tell him twice—he retains everything.” In addition to helping Doll at her farm, Riley also takes care of his green pony, Doll House Fancy Flight, at home.

Shannon and Riley dominated the circuit in 2014 and 2015, until an injury in mid-2015 left Shannon out of commission. That’s when the family tried stepping “Midge” up to the plate. Riley drove Midge in a few events, even winning the Windridge Horse Driving Trial in North Carolina, but spookiness and overall greenness showed that another pony would be more beneficial for learning.

Professional driver Allison Stroud ended up answering their pony prayers. “We went to an event and met Tracey Morgan, and she is friends with Allison and offered the pony because he was retiring from the team, but wanted him to keep going,” Billie says. “So currently Riley is using her pony, Mosby, that has competed all over the world. It’s an amazing opportunity because the pony can teach him so much.”

The two clicked instantly, and have a promising future. Mosby has spent the winter down in Florida, with Riley flying back and forth for lessons and shows. “He is an amazing and smart pony,” Riley says. “He’s also very brave.”

Florida is a lucky place for the Wiltisons, with their chance Chester Weber encounter happening at an event there in the winter of 2015. “Riley follows Chester—he’s one of his driving heroes,” Billie says. “So we go up and introduce ourselves, and I’ve never seen Riley so starstruck.” Weber was impressed with Riley and invited him to drive a bit at his own farm. “During Live Oak [International in Ocala, FL] we took Shannon, not to compete, but just to play with Chester after the competition. He was wonderful with Riley. I was so impressed. Riley was looking down, so Chester had him chase him through the obstacles.” (Editor’s note: the video is on YouTube, and it’s hilariously heartwarming—check it out!)

While he might seem like any other ponycrazed kid, Doll believes Riley is driving far beyond his age—an amazing feat. “Tracey Morgan said to me, ‘He learns quickly.’ Any new thing that you present to him—he’s got it,” Doll says. “You don’t have to keep at it. He loves trying different things like, ‘Well, if this isn’t working, what else can we do?’ He’s just always thinking.”

As for the future, Riley has one big goal. “I want to beat Chester Weber in the world finals!” he says with conviction. Watch out, Chester—from the looks of it, Riley’s right on your heels.

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