There is certainly a glamorous element to hoboing, but often hoboes caused problems for railroads.
Consider an episode that took place on the Lousiville & Nashville Railroad in October 1911. Two hoboes entered an empty baggage car on train No. 104 as it departed from Memphis, “fastening themselves” inside.
The men refused anyone, including the train’s conductor, to enter the car, according to a newspaper report. The happening did not stop the train from steaming toward Clarksville, Tennessee.
When the train arrived in Clarksville, the conductor, a man named Sellers (possibly famed conductor Francis “Frank” Marion), sought help from the local police. He then broke the glass on an end door of the car in a bid to enter and apprehend the pair.
As the conductor and police offers were about to enter the car, the hoboes opened a side door and jumped out, hoping to escape. Authorities “nabbed” the men before they secured their freedom.
Officials threw the men in the hoosegow. The next morning a local judge arraigned the men, said to be from Eddyville, Ky., and fined them each $5, according to a report in the Clarksville Leaf-Chronicle newspaper from the time.