Most recently famous for earning individual silver at the 2008 Four-in-Hand World Driving Championships held in Beesd, The Netherlands, Chester’s success in combined driving started early. At 18 years old, he was the youngest driver to be named to the United States Equestrian Team (USET) and to qualify for the World Pairs Driving Championship. By 1999 Weber had won 12 consecutive Advanced combined driving events and then transitioned to Four-in-Hand driving, where he has not only made a name for himself internationally, but since 2003 he has stockpiled an unprecedented streak of six National Championships in a row in the United States.

At the 2002 FEI World Equestrian Games, Chester earned team silver and placed 5th individually in Jerez, Spain. In July 2004, he became the first American to win the prestigious German Fahrderby held at CAI-A Riesenbeck, an achievement he handily repeated in 2008. In 2006 he again represented the United States at the FEI World Equestrian Games, finishing 8th.

In addition to his rigorous competition schedule, Weber actively promotes the sport of combined driving. He serves at the highest levels of the sport in the United States Equestrian Federation (USEF), currently on the Board of Directors, the High Performance Driving Committee, the National Driving Committee, the Safety Committee and Chairman of the Active Athletes Committee.