By Ryan Adams
Ryland Wakeley Sr. was born in Chicago’s Beverly Hills neighborhood, a slightly less bougie part of town compared to the California city of the same name, in 1915. As a young child growing up in Chicago, one day Ryland found himself cruising on the back of a neighbor’s Harley-Davidson, watching the pavement fly by beneath him. It was at that moment the fire was lit. A lifelong passion for motorcycles, specifically Harley-Davidson, would ensue. From then on, whatever he had going on in his life, he made sure he had a motorcycle.
It was June 15, 1934, when 18-year-old Ryland Wakeley bought his first motorcycle, a 1928 Harley-Davidson JD, for fifty whole dollars. Working at a local drugstore at the time, he’d make deliveries for the shop on his motorcycle. Everyone in the neighborhood knew who he was, even if they didn’t know him by name, they knew him by the motorcycle.
Ryland Sr. (fourth from the left) began racing dirt track on his 1938 Harley-Davidson EL, a high-performance bike of the time, and the model which earned the name the “Knucklehead” due to the shape of its rocker covers.
As a child, Ryland and his family had vacationed in Muskegon, Michigan at a farmhouse the family owns and still uses to this day. Of course, as a motorcycle enthusiast, Ryland made his way to the local flat track to watch the races while they were visiting. Five years after buying his first bike, he picked up a high-compression (8.5:1) Harley-Davidson EL to begin racing. While his mother didn’t approve of his racing, he eased her nerves by telling her he only participated in the “slow races.”