by Chris Lomon

His travels have already taken him to places he never envisioned, but there are many more miles and destinations to come for Kiwon Waldron.

Dreaming big and chasing those dreams has been part of the young horseman’s life for as long as he can remember.

Growing up in Bermuda, a British island territory that is home to just under 64,000 inhabitants, Waldron became fascinated with horses at a young age.

It was no longshot that he took an immediate liking to them considering his grandfather had horses and was a carriage driver, and his brother and an uncle both raced trotting ponies.

“I loved being around the horses,” Waldron said. “I would ride ponies and that was always fun. I knew I would end up working with horses one day. I wasn’t sure at one point what that would be, but as time went on, I found that becoming a driver was my goal.”

Devonshire Parish, one of nine parishes found in Bermuda, is home to the only standardbred racetrack in the North Atlantic Ocean nation.

As noted on the Driving Horse and Pony Club of Bermuda website, “Harness racing is a worldwide sport but in Bermuda, the challenge of racing has higher demands due to the size and shape of our racetrack. Competitors and spectators feel the power of the ponies as they strive to do what they do best, which is go fast and win. This sport requires dedication, determination, and commitment from its competitors…”

Waldron is the very definition of dedication, determination and commitment.

Knowing he would have to leave Bermuda to advance his career, Waldron, as a young teenager, got his first experience with the U.S. harness racing scene when he competed on the Indiana fair circuit.

Then, six years ago, upon graduating from high school in his homeland, Waldron, with a little help from the racing gods, met high-profile Canadian trainer Rene Allard when the latter was in Bermuda with a friend to take in the biggest day on the racing calendar.

It led to an invitation from Allard for Waldron to compete in Quebec.

Racing at the fairs, while navigating a completely different culture, Waldron quickly impressed those he met, his down-to-earth nature and skills in the sulky endearing him to horse people wherever he found himself competing.

On July 13, 2019, he made his first pari-mutuel start on North American soil, specifically, Hippodrome 3R in Trois-Rivières.

Waldron was hoping to make it as memorable as possible.

In rein to Shemaksmefelunreal, a daughter of Sunshine Beach—Dreamfair Orchid, the pair set the early tone and led by a length after a quarter in :30.4, pushing their advantage to 1½ lengths through a half in 1:03.3.

At the three-quarter mark, Shemaksmefelunreal, the 4-5 choice, was only a neck in front.

Waldron called upon the Michel Allard trainee for her best and she responded, pacing the final quarter in :29.3 to secure a one-length score in 2:05.4.

“The greatest feeling you can have,” said Waldron. “I was so happy and to see how happy everyone else was made it even more special. I will always remember that day.”

The final four months of 2019 were spent traversing the Circuit Regional des Courses de Chevaux du Quebec.

Waldron produced gaudy numbers, fashioning a remarkable 14-7-1 record from 26 starts.

Putting up head-turning stats was not the biggest takeaway for the young horseman.

“Just learning and improving was so big for me,” he said. “The more chances you get, the more education you get. That was huge for me.”

Nearly three years ago, Waldron was in the sulky for Pompano Park qualifiers — he obtained his ‘P’ license in the Sunshine State — before he headed back north to Allard Stable in Quebec a couple months later.

The result of his hard work yielded a 17-12-13 mark from 131 races, accompanied by $59,436 in purse earnings.

Waldron was also feted as 2022 Rookie of the Year at Hippodrome 3R.

The news spread quickly, in this instance, over 1,050 miles away.

Bermuda’s only daily newspaper, The Royal Gazette, founded in 1828, heralded Waldron’s success.

But it hasn’t always been headlines and hurrahs for the personable 24-year-old.

In 2023, Waldron endured no shortage of tumult in trying to secure paperwork to stay in North American on a permanent basis.

Despite the delays, challenges, and other hurdles, he remained resolute throughout the process.

This May, the visa request was approved.

“I am so grateful to the Macombers [Indiana horsepeople Jamie and Ricky Macomber],” Waldron said. “I wouldn’t be here racing without them. From their hard work helping me with paperwork and giving me a shot to accompany them here – they have been great to me in so many ways.”

Competing at Hoosier Park, Waldron is very much feeling right at home in his U.S. Midwest surroundings.

He posted his first victory on the campaign on July 27 when he teamed with Airbus to earn a dead-heat win in 1:54.4.

“My friends owned the horse and that was their first win at Hoosier,” he said. “It was a full-circle moment, to be able to win that for them. It was awesome.”

Waldron has kept things rolling since then.

As of Nov. 26, he has 13 wins, 16 seconds and 13 thirds from 171 starts, along with $174,989 in purse earnings, on the year.

“I had a lot of fun driving the colt Spirit And Heart this year,” said Waldron of the 2-year-old son of Luck Be Withyou—So Long my Love. “I have had some other very nice horses too. I am very lucky to get those opportunities, and I want to make the most of them.”

The pride of Warwick, Bermuda, is grateful for the success, but eager to chase more.

“I am seeing how I can finish the year in a positive way, hoping the horses race well and get the results we are looking for,” he said. “After that, I don’t have anything set in stone. I might go to Hawthorne and see if I can get some drives there.

“Wherever I go and whatever I do, I just want to keep building and learning.”

Waldron, an avid golfer, has continued to heed the advice imparted to him back home and when he first came to North America.

“I was told, ‘Don’t ever give up,’” he said. “If I have a bad drive, I need to put that behind me and focus on the next race. My goal is to give the horse I drive the best chance to win.”

Support, in the U.S. and Bermuda, remains a constant.

“My family has never stopped believing in me, especially my mom, who is my number one fan,” Waldron said. “She came here to Indiana not too long ago and she got to see me drive in person. She always keeps me going. We talk every day. She sends me good luck messages and keeps me grounded. Everyone back home, it is nothing but love.

“I have had so many great people provide me with opportunities and believe in me. All the credit goes to everybody who put my name down to drive their horses. They gave me a shot. Without them, I wouldn’t be anywhere. But I am so happy to be where I am.”

And just as happy for where it all might lead.

“I know everybody who drives says the dream is the Grand Circuit, but for my long-term goal, I want to go as far as I can for as long as I can in this industry and sit behind champions,” Waldron said.