He began riding at the age of eight, taking weekly lessons at a stable that housed carriage horses in downtown Chicago.

[2][3] Throughout his junior career, Farrington primarily engaged in catch-riding, showcasing his skills on horses he was unfamiliar with for various industry professionals.

[5] At the age of 18, Farrington won a gold medal at the 1999 North American Young Riders International Competition[6] which started his career, working with US two-time Olympian Leslie Howard.

[7] He received the Maxine Beard Award, presented to an American rider who is judged to be excellent at displaying potential to represent the United States on the international stage.

[9] Farrington became the first American to win the International Jumping Riders Club (IJRC), the Rolex Top Ten Final (2015), and the Queen Elizabeth II Cup at Spruce Meadows (2017).