Born in Racine, Wisconsin, Della was 29 years old and making her living in Waco as a manicurist when a young family member suggested she take up motorcycle riding as a way to see more of the local scenery she enjoyed so much. That fall, she had bought a new 1913 Harley-Davidson single-cylinder bike and took up riding around town. The next spring she traded it in for a twin, and had a sidecar bolted to it, in preparation for a months-long tour.
Her first destination was the July 3 motorcycle races in Dodge City, Kansas. With today's modern roads it would be a one or two-day trip but things were different in 1915. An extremely wet winter and spring made roads across Texas and Oklahoma badly rutted mires of mud and sand. And if that weren't enough, there was the added danger of hidden stumps, logs and rocks in the so-called roads. All those miles of sand beds and rugged hills took their toll on both the rider and the motorcycle.
Despite a collision with a stump which knocked her sidecar out of line, Della made it to the paved streets of Oklahoma City without a major mishap. The 75 miles of macadam in the city were a welcome relief to Della, but upon entering Kansas, heavy rains made the roads such a quagmire she had to install tire chains. Finally, even chains couldn't provide enough traction and with Trouble in the sidecar, Della struck out through four miles of Kansas wheatfields before finding a usable road. She made it to Dodge City in time for the race, one of the premier motorcycle events of the time.
Deciding to see the country along the way North, the pair headed through the beautiful scenery of Missouri. With good weather and fine roads, they made good time as they raced up one hill and down another. The trip to Chicago and then to the Harley-Davidson factory in Milwaukee was comparatively quick and uneventful.
After leaving Milwaukee, they headed south into Indiana where authorities stopped her twice because of the dog. There was a quarantine in Indiana because of hoof and mouth disease and Della had to promise that her dog wouldn't leave the sidecar before they could proceed. Nevertheless, upon arriving in Goshen, Indiana, they were invited to participate in a local parade giving them the opportunity to see the city, so it wasn't until autumn 1914 that she started across toward the East Coast.
From Waco to Milwaukee to New York City with numerous side trips, Della and Trouble logged 5,378 miles and their motorcycle performed flawlessly. As Della stated after completing the journey, "I had a glorious trip. I am in perfect health and my desire is stronger than ever to keep going."
She would reach New York City in the dead of winter and as she celebrated her achievement in New York, Europe was already engaged in World War I, which meant her plans to travel around the world no longer seemed possible.
So, she booked passage to Florida instead. From Florida her next port of call was Havana, where she met with other local riders and toured all over the island. Then she hopped another boat and visited Panama and "America's master work," the recently opened Panama Canal.
Della next landed on the island of Jamaica, part of the British Empire at the time and still very much an unspoiled tropical paradise, where she motored to the top of the highest peak. Della's last stop on her Caribbean tour was an extended stay in Puerto Rico
She returned to the USA via Tampa, then to Atlanta, and proceeded to visit the Carolinas, Washington, D.C., and Philadelphia before reaching New York City once again – racking up 10,778 miles.
According to the Texaco Star story, Della departed New York for Los Angeles in 1916, but history says Effie and Avis http://justacarguy.blogspot.com/2018/05/mother-and-daughter-on-their-way-to-pan.html were the first women to make that trip, so, she missed setting a record by months.
Della settled in Los Angeles afterward, and census records have her in Compton in 1926 – working as a manicurist again, as well as a shop clerk. After 1926 she vanishes from the voter roles, so nobody really knows what became of her, but for those glorious few years in the teens she lived the adventure of a lifetime.
https://www.femaleriders.co.uk/single-post/2017/08/21/Della-Crewe-%E2%80%93-5378-mile-trip-in-1914-Where-She-Goes-Trouble-Follows
http://www.forensicgenealogy.info/contest_405_results.html