The rich and diverse hobo history of America started in the mid-to-late 1800s and continues even today. As Civil War veterans returned to everyday society, many set off on trains looking for work as the country rebuilt itself. Decades later, the Great Depression expanded these practices and economic needs to travel for work, increasing the number of vagrant workers who moved across America in search of income and new lifestyle opportunities. According to Todd DePastino, the author of Citizen Hobo: How a Century of Homelessness Shaped America, that's when the image of the hobo was fixed in the American consciousness.

The hobo lifestyle is still intact in modern times, though it has changed over the years. Today's homeless individuals tend to skew younger than their historical counterparts - and their motivations and practices often extend far beyond economic disparity. Although many hobo practices that developed during the early 20th century are still used, modern hobo culture has adapted alongside American society, thanks in part to technology and changing forms of communication.