When his parents divorced, and his mother remarried, he moved to South Africa at the age of 15, where his family owned a citrus farm at White River.
After completing his education at St. Andrew's College,[3] Fairfield's family believed he needed to gain a suitable degree to manage the farm, and so he applied to the University of Cambridge; average exam results at the time meant his application was unsuccessful.
[6][7] Fairfield met his future wife Jean Beckett at Cambridge and the completion of his studies, the couple returned to South Africa where they settled at White River and began farming.
In England, Fairfield joined with Cyril Paul, another young and inexperienced racing driver, with the two working under Freddie Dixon in his Middlesbrough and Brooklands.
After his victory at Crystal Palace, Fairfield traveled to France to take part in the 24 Hours of Le Mans, where he drove a Frazer Nash–BMW 328 with David Murray.