By Jim Fricke, Harley-Davidson Museum® Curatorial Director

Della Crewe and her dog Trouble, outside the Harley-Davidson factory in 1914. Harley-Davidson Archives Photo


Featured in H.O.G.® Magazine Issue 010

At a time when the sorry state of American roadways would have made even the hardiest of men think twice about making a cross-country trip, a young woman showed them how it was done. An article in the August 1914 issue of The Harley-Davidson Dealer begins: “All the fellows around here who have been bragging about their abilities as road riders are strangely quiet these days.

And a woman has silenced them. Miss Della Crewe is the name of the quiet voiced woman who put the damper on the loud talkers. Since her arrival here, with her Harley-Davidson two-speed twin and sidecar, from her home in Waco, Texas, no one has dared complain about bad roads or boast of going through stuff that no one else ever went through before.”

A Wisconsin native, Miss Della Crewe was an experienced traveler even before she started on her motorcycle odyssey. She had traveled through much of North America and up to Alaska, and lived for seven months in Panama. It was a visit to her hometown of Racine, Wisconsin, that put the idea of getting a motorcycle in her head. Della remarked on the number of motorcycles she observed on Wisconsin roads, and her nephew suggested that a motorcycle would be “just the thing for you to travel all over with.” He was joking, but she liked the idea.


Della Crewe was greeted by company founders William Davidson (left) and Walter Davidson (right) when she visited the Harley-Davidson factory in 1914. Harley-Davidson Archives Photo


Back home in Waco she purchased a two-speed single and began to plan an around-the-world trip. Just before she planned to leave, a fierce storm washed out roads and bridges for many miles in all directions. Her friends urged her to have her bike shipped outside of the destroyed area, but she insisted that she was going to start her travels from Waco, Texas and “make every mile a Harley-Davidson mile.” While waiting for the storm damage to be repaired, Miss Crewe decided that a sidecar would be a great asset in her travels. So she traded in her two-speed single for a two-speed twin with sidecar. On July 24, 1914 Della Crewe, loaded 125 pounds of supplies into that sidecar and set out on a rambling journey to New York City. As a parting gift the people of Waco presented Della with a thoroughbred Boston bull pup, intended as a constant reminder that they wanted her to return home. Della named her new companion Trouble and stated, “Trouble is the only trouble I will have with me on this trip.”

Della’s first stop was the July 3rd motorcycle race in Dodge City, Kansas, a side trip that added 300 miles to her route to Milwaukee. At a time when downed bridges and washed out roads regularly added hours to even a short trip, this was a major detour. But Della was determined to attend the race, which was the “Indy 500” of its time. She recounts that near Kiowa, Kansas the roads were so deep with mud that she cut through a fence and traveled four miles through a wheat field. “I rode up to the farm house to pay for the damage which I had done. The farmer looked at me with surprise and said ‘If you have pluck enough to travel through this country the way the roads are now, I could not think of charging you for the little damage you did to my fence and wheat field.’ That gave me fresh courage and kept me going until I reached better roads.”

Della pulled into Dodge City having braved 973 miles of rough road, gaining the admiration of everyone who heard her story. And she was just getting started ...


Of all the spectators at the 1914 Dodge City 300, Della Crewe and Trouble were judged to have traveled the longest distance by motorcycle to attend the race. Harley-Davidson Archives Photo


From Dodge City, Della visited a sister in Sterling and passed through Kansas City on her way to St. Louis, Missouri for the annual convention of the Federation of American Motorcyclists, the predecessor of the American Motorcycle Association. Miss Crewe then made her way to Chicago where she was greeted by C. H. Lang, Harley-Davidson’s first dealer, and Mr. R. F. Rogers, owner of the company that made her sidecar. Rogers then accompanied her to visit the Harley factory in Milwaukee. She observed, “When I arrived in Milwaukee, I had passed through six states and my expenses had not exceeded $25.” By this time, Miss Crewe had also logged 2,147 miles. While in Milwaukee, Miss Crewe visited the factory and met Harley-Davidson’s founders. As a special treat, Harley-Davidson’s stenographers—the largest group of women at the factory--arranged a picnic at nearby Castalia Spring in the upper Menominee valley.


Della and the Harley-Davidson stenographer pool prepare to leave the factory for a picnic, 1914. Harley-Davidson Archives Photo


After leaving Milwaukee, Miss Crewe traveled south back through Chicago into Indiana where it has been reported, she was stopped not once but twice because of Trouble. Indiana was under quarantine for hoof and mouth disease in 1914, and Della reportedly had to promise authorities that Trouble would not leave that sidecar until they were safely out of Indiana.


Della and Trouble on the road, pictured in an account of her trip in an unidentified publication ca. 1914. Harley-Davidson Archives Photo


Having spent the summer and fall months traveling from Waco to Milwaukee, Della found herself battling cold weather and snow-covered roads while traveling through Indiana, Ohio, Pennsylvania and New York. With temperatures below zero and snow drifts above her head, she reported one instance when it took two hours to cover only 2-1/2 miles. She arrived in New York City on December 10, 1914 “weighted down with four pairs of stockings, sheepskin storm shoes, heavy dress, one sweater, two coats, two hoods.” Trouble rode out the cold “snuggled in the bottom of her car” in a special made-to-order sweater. They had traveled 5,378 miles and covered ten states over a span of six months. Upon her arrival in New York, Miss Crewe stated: “I had a glorious trip, I am in perfect health and my desire is stronger than ever to keep going.”

Della had originally planned to sail to Europe and travel through that continent, but the outbreak of World War I compelled a change in plans. In January 1915 she and Trouble headed down the coast to Florida, hoping for sun and clear roads. Finding the weather in Florida worse than what they’d left in New York, they spent 5 weeks in Jacksonville waiting on the sun to dry out the treacherous coastal road to Miami. Through the spring and summer of 1915, Della toured the Caribbean, first visiting Cuba, then taking a United Fruit steamer to Panama, from there on to Jamaica, and finally visiting Puerto Rico. She returned stateside in midsummer and made a meandering journey up the Atlantic coast. Della and Trouble arrived back in New York City having traveled 10,778 miles since leaving Waco a little more than a year earlier.


Jamaican sites visited during Della’s Caribbean tour in 1915. Motorcycle Illustrated, December 9, 1915


Della’s Caribbean adventures were chronicled in a series of stories in Motorcycle Illustrated published in 1915, with further tales of her Atlantic Coast trips appearing in the August, 1916 issue of the Texaco Star. In that last account it is noted that she “has just started on another tour from New York to Los Angeles.” We lose track of her at this point, but the 1920 U.S. Census shows her living south of L.A. and working as a manicurist. It’s difficult to believe that her motorcycling exploits ended there, but whatever happened next is lost to history. The well-documented stories of her yearlong journey have inspired generations of riders who feel, as she did, that “the call of the road is in everyone; the cry of the heart is to get near to nature.” It’s fun to imagine where Della and Trouble might have gone next. Perhaps someone reading this account will provide a clue …

For more stories like this, visit the Harley-Davidson Museum® in Milwaukee. As a H.O.G.® member, your admission is always free!