Leroy Winters was the first rider to win the Jack Pine Enduro aboard a lightweight motorcycle. He did it on a German-designed but Harley-Davidson-branded DKW 165.
Winters was one of the first riders to capitalize on the bikes. He modified the motorcycle for the grueling Jack Pine Enduro and claimed victory in 1956.
That was just the start of Winters’ off-road success. Later in his racing career, the Fort Smith, Ark., rider became an international ambassador for U.S. off-road. He increased his prominence in the sport significantly by competing in the International Six Days Trial from the mid-1960s through 1972. He won a silver medal twice in the World Championship event riding for Team USA.
Winter’s connection to the ISDT was so enduring that in 1995 his club, the Razorback Riders in Arkansas, organized an ISDT reunion ride. Winters died in 1998 and the event was renamed the Leroy Winters Memorial.
The April 1955 issue of American Motorcyclist had this to say about Winters: “Little 135 lb. Leroy Winters of Fort Smith, Ark., lived up to the name of ‘Arkansas Traveler’ as he traveled over the rugged 70-mile enduro course to win the Handlebar Derby event on a swinger-arm 165 Harley-Davidson to outclass a record field of more than 80 riders with a score of 971.”
Leroy Winters was inducted into the AMA Motorcycle Hall of Fame in 1999.