Holly Hudspeth (née Hepp) has been around the country’s biggest events on horses like Last Monarch, Damien and Lester Piggott, but she never quite understood the nerves her family and friends felt when she headed out of the start box.

That is, until her daughter Hailey Hudspeth decided to pick up the sport.

Aboard a pony named Cookies N’ Cream, Hailey has been confidently trotting, and now cantering, around starter events at the Carolina Horse Park’s War Horse Event Series in Raeford, North Carolina. Following in her mom’s successful footsteps, she picked up a win in her first outing at the maiden (2’3″) level on May 16.

Hailey Hudspeth and Cookies N’ Cream. Photo Courtesy Of Holly Hudspeth

“I’m a nervous wreck! It’s so nerve-wracking,” Holly said. “As a competitor who’s gone through the top levels and competed overseas, I’ve pretty much made every mistake you could make and had to learn from it, so I have to rein myself in to not try to give her too much information. Taking her to the start box is really nerve-wracking, and I don’t know why because I trust the pony so much.”

“It was my first maiden, and I just wanted to take it easy,” said Hailey. “It was really fun to ride her. It felt really good to win. I was really proud of her.”

Hailey Hudspeth and Cookies N’ Cream jumping around their first maiden. Brant Gamma Photography Photo

Hailey only recently started cantering fences in competitions.

“We talked about how, when the jumps get bigger, you need to go forward, so she did,” Holly said. “She just went out and let it rip, and I was like, ‘Holy smokes!’ When she comes across the finish line, now I know how my family felt when I was competing. It’s not easy.”

Hailey Hudspeth and “Cookies” after their big win at the War Horse Event Series with her dad, Chuck Hudspeth, and Kiera Kenny, Cookies’ former owner. Photo Courtesy Of Holly Hudspeth

Hailey wasn’t interested in riding, Holly said, until one event when a client’s father took her to the tack store and bought her a brush and a rub rag. After that, Hailey needed a pony to use them on, so Holly, who runs a training business out of Equiventure Farm at Quail Roost in Rougemont, North Carolina, set about finding something to get her started.

Young rider Kiera Kenny was looking for “Cookie’s” next rider, so she sold the 19-year-old Welsh cross mare to Holly.

“She has taught 10 kids to ride. She has evented with all those kids through novice,” Holl said. “She is an absolute unicorn.”

Holly Hudspeth got this card from her parents when she got her first pony when she was 9. Photo Courtesy Of Holly Hudspeth

She made one for Hailey, who also got her first pony when she was 9. Photo Courtesy Of Holly Hudspeth

Hailey, who is almost 10, started riding with Megan Ward at Triton Stables, doing her first longeing sessions, then her first trot, canter and jump. She went to some walk/trot and crossrail hunter shows. Her focus turned to eventing when Cookie joined to the family a year ago.

“She’s really fun to ride, and she’s very smooth, and she will always listen to me,” Hailey said. “She’s pretty brave, even though she’s a pony.”

Holly said she misses competing herself, but with a busy business and helping Hailey, she hasn’t had time for the past few years.

“I still travel to the horse shows, but when Hailey took off with her riding and with all the people I take to the shows, it’s really tough for me to carve time out to compete myself,” she said. “There’s not enough hours in the day for me to compete as well.

“I miss it a lot. It’s always hard when Fair Hill [Maryland] and Kentucky roll around. I miss the thrill of the competition. I think with her and school and everything else she’s got going on, there’s the day-to-day grind I don’t miss, but I miss competing at the upper levels.”

Hailey’s first horse show in 2018. Photo Courtesy Of Holly Hudspeth

Hailey said she’s inspired by watching her mom, as well as riders like Boyd Martin, Phillip Dutton and Doug Payne. She’s seen videos of her mom riding around the Land Rover Kentucky Three-Day Event.

“I love to watch her ride,” she said. “It teaches me something. I’m really lucky to have a mom like her that teaches me so good because she’s a rider.”

Holly isn’t sure how far Hailey will go in the sport, but she has a horse cued up for when she’s ready. One of Holly’s students, Cindy Deporter, has a novice level mare named Ana D who she will pass down when she’s done riding her.

“She’s informed me that Cookie will never be for sale,” Holly said with a laugh.

“I’m so lucky to have such a great teacher in a pony like her,” Hailey said. “She’s really brave. A lot of the other horses are like, ‘I don’t know what to do,’ and then Cookie is like, ‘Oh, I know what to do, and I’ve been there, done that.’”

“We thank our lucky stars every day for her,” Holly added.