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Originally, a hobo was an itinerant worker. Hobos travelled from town to town doing seasonal jobs that only lasted a short amount of time. The term dates back to at least the great depression where most hobos got from town to town by illegally riding freight trains. In some parts of the world, the term hobo has come to be a generic term for a homeless person.
A hitchhiker is someone who travels around by begging lifts from drivers that they meet (or flag down). They might be traveling for work or for recreation.
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