Chester Weber

Written by: Kelli Fuqua Hart, Executive Editor | Photography by: Chris Redd, Chief Photographer

Chester Weber is a name known around the globe – a name that is, according to, “…synonymous with Four-in-Hand driving.” His family has built a business empire but Weber’s legacy goes beyond his family’s fortune. Weber is a stand alone world champion and Ocala is fortunate to be the place he calls home.

The most successful combined driver in the nation, Weber has helped put Ocala on the map. Likewise, he has put his 4,500-acre farm, Live Oak Stud on the radar, being home to not only his magnificent estate but his award-winning Thoroughbred racehorses.

At just 18-years old, Weber’s passion for combined driving ignited. It was at this time he was named to the United States Equestrian Team and as the team’s youngest driver, he qualified for the World Pairs Driving Championship. Weber’s list of accomplishments and accolades is lengthy and one he should be proud of. In fact, it’s a list Ocalans can be proud of as it has given both national and international attention to our city.

By 1999, Weber claimed victories in 12 consecutive Advanced combined driving events. In 2008, Weber made history becoming the first American to win an Individual Silver Medal in the Four-in-Hand World Driving Championships. In 2014, Weber won the Four-in-Hand International Driving competition, resulting in a royal handshake by Her Majesty, Queen Elizabeth II. Weber has already started collecting wins in 2016, taking the title at the Little Everglades Combined Driving event. In between these prestigious awards are numerous others that Weber has won over the course of his successful career.

Not only a competitor, Weber takes the reigns when it comes to organizing the annual combined driving event, CAI Live Oak. Ironic enough, in its inaugural year, Weber found himself unable to compete in his own event because he was not yet 18-years old. Now celebrating its 25th year, this event has grown by leaps and bounds, becoming one of the largest Combined Driving events in the world. The show draws crowds by the tens of thousands each year – spectators looking to watch the world’s best drivers compete.

Originally a world-class driving event, Weber debuted Show Jumping in 2012 and the combination of the two events was a success. “For the first time,” according to, “a world-class jumping event and world-class driving event were together at a world-class farm on the same weekend.”

Weber’s farm is the perfect setting for such a prestigious event. For over 40-years, Live Oak Plantation has had a winning reputation, leading the industry in thoroughbred racing, foaling, breeding and training. Tucked away under a magnificent oak canopy, Weber’s farm is inviting and the events are highly anticipated each year.Guests took advantage of glorious weather, attending the events and taking in the sport. Throughout the event, spectators enjoyed both combined driving and jumping competitions. On February 27th, drivers took part in the always exciting marathon, where each driver maneuvers their horse, or horses, through a complex pattern of fences in the quickest time possible. The event closed on February 28th with the final phase of Combined Driving. Drivers took to an obstacle course where they performed designated patterns through pylons in the fastest time possible and with hopes of not knocking down any of the pylons.

Jumping competitions were held Friday and Saturday, with the $100,000 Longines World Cup™ Qualifier closing out the event. The qualifier is part of the inaugural Longines FEI World Cup™ Jumping North American League.

In the end, Weber took home his 13th USEF Four-in-Hand National Championship. Sweeping all three phases of the combined driving competition, Weber earned his gold medal with an overall score of 173.20. “I couldn’t be prouder of my family and the whole team’s effort to get this done,” Weber stated after the conclusion of a successful Live Oak International event. “The City of Ocala and the 900 horse farm owners and people who are interested in horses around here… it’s almost shocking.”

Suzy Stafford competed in the FEI Single Horse class with her Hall Of Fame Morgan PVF, Peace of Mind, and won the cones phase on Sunday to post her own sweep in the class. Stafford completed the competition with a score of 138.65. Peace of Mind, known as “Hunny,” was the 2015 USEF International Horse of the Year and was named to the Horse Stars Hall of Fame for 2016.

Allison Stroud won silver in the Four-in-Hand class with a score of 211.61. She finished second in the marathon phase and third in dressage. Bronze went to Craig Grange for a United States sweep of the Four-in-Hand, while Leslie Berndl of the U.S. was second in the cones for Single Horse. Her cones test was good enough to edge her into second place overall in the class.

For full results and more information on Live Oak International and Chester Weber, visit

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