One of the more memorable motorcyclists during the 1910s — an era that has been characterized as the Golden Age of American Motorcycling — was a woman named Della L. Crewe. She was born in Wisconsin in 1884 and eventually made her way to Texas. By 1910, she was living in Waco and working there as a manicurist.
Crewe loved to travel, so she readily acted on a nephew’s suggestion that she take a long-distance trip on a motorcycle. On June 24, 1914, she began her ambitious journey riding a newly acquired Harley-Davidson Two-Speed Twin motorcycle with a sidecar. Crewe loaded up the sidecar with 125 pounds of supplies. She also left Waco with a Boston bull pup that some friends given to her to keep her company on the trip. Crew named her new canine companion Trouble. As she explained, “Trouble is the only trouble I will have with me on this trip.”
Crewe’s ultimate destination was New York City, but she made a number of stops en route. One of the earliest and more significant of these stops was part of a detour she took to Dodge City, Kansas, where the first major motorcycle race in the U.S. was being held on July 3. Crewe made it to the Dodge City 300 race just in time, and then traveled to St. Louis for the annual convention of the Federation of American Motorcyclists (now part of the American Motorcycle Association) in mid-July. From that event, Crewe and Trouble continued their trek on often rough and muddy roads to visit both Chicago and Milwaukee. The traveling pair eventually made their way through Indiana, Ohio, Pennsylvania, and New York even as the weather grew colder and all the more challenging and many of the roads continued to be anything but ideal.
Finally, in December 1914, a heavily clad Crewe rode her motorcycle into New York City on a chilly day. She was reportedly wearing four coats, four pairs of stockings, and sheepskin shoes, while Trouble was outfitted with a sweater. “I had a glorious trip, I am in perfect health and my desire is stronger than ever to keep going,” Crewe proclaimed after reaching New York City. Her motorcycle trek of 5,378 miles not only proved to be successful but earned her nationwide fame.