1956 Harley-Davidson 165

There was a time in the late 1950s when, thanks to the ingenuity of future Hall of Famer Leroy Winters, Harley-Davidson was on the cutting edge of the lightweight off-road movement.

Back then, Michigan’s grueling, two-day, 500-mile Jack Pine Enduro was the biggest off-road event of the year. From 1923 through 1955, the Jack Pine had been held 28 times. Harley riders had won it 22 times.

All of those wins came on heavyweight bikes designed for road use and only slightly modified for rough terrain. Conventional wisdom held that you needed lots of power, wide tires and lots of weight on the rear wheel to win in the deep sugar sand of Michigan.

Winters had a different idea. He began with a diminutive two-stroke machine that carried the Harley-Davidson name even though it was designed by the German DKW firm. The U.S. rights to the highly regarded DKW 125 were awarded to Harley-Davidson as part of Germany’s World War II reparations. It was then enlarged to become the 165.

Winters, who was diminutive in stature but wiry and very strong, modified the 165 for the dirt and rode it to victory in the 1956 Jack Pine. He beat riders on machines with four or even six times as much displacement, surviving a course that eliminated three-quarters of the entrants.

Harley-Davidson featured Winters’ victory in its advertising that year, noting that it gave the company the distinction of being the first lightweight motorcycle to win the 500-mile AMA National Enduro Championship.

Winters’ victory was a prelude to the future. A decade later, the two-stroke, lightweight movement was going strong, led by European manufacturers, such as Husqvarna, and the U.S. Penton brand, with the Japanese soon following.

Winters’ winning bike is owned by the Winters family. It is on display at the AMA Motorcycle Hall of Fame in Pickerington, Ohio.