Leroy Winters was the first rider to win the Jack Pine Enduro aboard a lightweight motorcycle. He did it on a German-designed, Harley-Davidson-branded DKW 165. He modified the motorcycle for the grueling enduro and claimed victory in 1956.

Prior to Winters’ triumph, the race, and off-road competition in general, was dominated by heavy, multi-cylinder bikes more suited for the high speeds of flat track or touring the countryside.

Although it would be another decade before the tide would officially turn from the larger four-stroke twins, Winters was one of the first riders to show that horsepower wasn’t so important in the tighter confines of enduro racing. Instead he, and others following him, would learn to capitalize on the quicker handling and lighter weight of smaller machines.

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 competition. He increased his prominence in the sport significantly by competing in the International Six Days Trial (now the International Six Days Enduro) 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 posthumously inducted into the AMA Motorcycle Hall of Fame in 1999.