Of course there's the FALLOUT series. I think they have a similar feeling as being on the road.
Actually, most of those Post-Apocalyptic / Survival games have that feel. DayZ, Far Cry. Wander around with a vague purpose...
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But I think my favorite "travel" game, and you may disagree here, is Psychonauts. It's the closest to what it's like to meet all the free (and sometimes dangerous) people on the road. Raz, the protagonist, runs away from his circus performing family to become a psychic at Whispering Pines summer camp. Most of the characters have mental problems (which is too true for all of us, and all the folks you meet on the road). And you spend your time diving into their minds, picking their brain for stories and clues into what shaped them, and how to solve your own issues from their experiences. And, of course, being critical of and trying to figure out a government / secret institution plot while doing so. Beautiful story, and surprisingly dark, real, and hilarious for what looks on the surface to be a kid's game. The graphics seem dated now, but it's worth a play-through if you haven't gone on that mental voyage, yet...
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PSYCHONAUTS