06/12/2025
It’s wonderful that her little dog, Trouble, got to go with her on the adventure
In 1914, when most women were expected to stay close to home, Della Crewe packed her belongings, donned a long leather coat, and set off to see America—not in a car, not by train, but on a Harley-Davidson with a sidecar and her Boston terrier, Trouble, nestled right beside her. She wasn’t wealthy. She wasn’t sponsored. She simply believed women could go wherever they pleased, however they pleased. And she did.
Starting in Waco, Texas, Della traveled thousands of miles through cities and across rough backroads, facing harsh weather, mechanical breakdowns, and more than a few skeptical glances. But she kept going, undeterred. Her journey was a declaration: women didn’t have to wait for permission to explore the world. She posed for photographs in front of Harley dealerships, Trouble often dressed in goggles and a little sweater, the two of them looking completely at ease on the open road.
Della Crewe’s story may not be widely known, but her spirit lives on in every woman who refuses to be boxed in by convention. At a time when women couldn’t even vote, she was crossing the country on her own terms—with grit, independence, and a loyal dog riding shotgun.