Racing for Mercedes-Benz, he won his first two Hillclimbing Championships in 1930 and 1931, and moved to Alfa Romeo for 1932, where he won the Hillclimbing Championship for the third time.
Caracciola se je začel z dirkanjem ukvarjati kot pripravnik v aachenski avtomobilski tovarni Fafnir v začetku dvajsetih let, najprej z motocikli, nato še z avtomobili.