The economist Karl Polanyi, in his excellent book The Great Transformation (1944), pointed out that a true Free Market system, so beloved by American economists, needs a number of ingredients, including "free" (i.e. unfettered) capital, material and labor. The requirement that causes social dislocation is for "Free Labor," defined as the ability and willingness of workers to move to wherever the jobs are, and for pay that's determined by supply and demand, so there are neither labor shortages nor surpluses. This need is the major reason why the public eventually demands laws to protect us from the ravages of a Free Market. Once people own property, labor becomes sticky, and about the only place you'll find the economist's ideal is among migrant Mexican workers in California fields.
There are other causes for itinerance, of course. Historically, exile, whether of a group (all the diasporas) or an individual, is a key factor. Wandering could also be heroic, as in Odysseus's 20-year voyage towards home. But the American industrial revolution and westward expansion of the 19th century was unusual because people were less likely to be leaving somewhere than moving toward anticipated opportunity. This migration greatly increased after completion of the first transcontinental railroad in 1869. Anyone who dared catch a moving freight car could use free transportation to head west and further the Free Labor ideal.
Incidentally, "Hobo," "Tramp," and "Bum" are often used interchangeably, but by the 1920s, usage had stabilized, as quoted in Norm Cohen's Long Steel Rail: "A hobo is a migratory worker. A tramp is a migratory non-worker. A bum is a stationary non-worker." You can see why an itinerant would prefer to be called a hobo.
There were lots of songs, even romantic ones, associated with hoboing. The commonest ones have a restlessness theme that seems typically American. Laurie Lewis was mining an old vein, but her song, Restless Rambling Heart (1978) expresses the feeling in modern terms:
I guess the grass is always greener and the sun shines brighter
And the fish are always jumping on the far side of the hill.
The mountains are crying, the prairies are sighing,
And the ocean is waiting to talk to me,
And my restless, rambling heart just won't be still.
The Georgia Hobo is my favorite among a large number of related recorded versions (28 from 1925 - 1937, according to Meade, Spottswood & Meade's Country Music Sources) that deal with resisting the temptation, usually offered by a woman in Danville, VA, to settle down. The first printed version, The Reckless Hobo, was in a 1913 song booklet sold by itinerant blind musician Dick Burnett, who'd learned it from "someone from the west." Another blind musician who lived nearby, George Reneau, heard Burnett's version and modified it for a 1925 recording. The Cofer Brothers (Paul and Leon) from Georgia changed it yet again (or perhaps learned a related version) and recorded The Georgia Hobo in 1927 (OK 45099, reissued on Yazoo CD 2036, Hard Times Come Again No More, Vol. 1). I particularly like this version because it moves right along in an unsentimental fashion. The Seaboard Air Line was a railroad in the southeastern US. Before air travel, "air line" meant the shortest distance between two points. But it's hard to believe this 20th century Odysseus is really going to be satisfied back in Georgia.
1. Standing on the corner, a-smokin' a cheap cigar,
Waiting for a freight train, to catch an empty car;
You get on the tender, and I will ride the blind;
We'll go back to Georgia on the Seaboard Air Line.
2. I got off at Danville, got stuck on a Danville girl;
I'll tell you, boys, she was out of sight, she wore those Danville curls;
Wore her hair in fashion, and dressed in fashion, too,
But when I heard the freight train blow, to the depot I did go.
3. Walked up to the conductor, and I gave him a game of talk;
He says, "Your money or ticket will take you to New York."
"Have no money or ticket, pity me for I am poor."
"Get outa here, you dirty bum," and he slammed the boxcar door.
4. Well I was broken hearted, for I had no place to stay;
No money in my pocket, and I had to go that day;
All the freights had left me, and friends there I had none,
I bowed my head so humble, and this is what I done:
5. Passed around my derby, "Now, boys, you all chip in;
Ten thousand miles away from home, a-riding an old freight train;
My pocketbook is empty, my heart is full of pain;
If I ever get back to Georgia, I'll never bum again."