This 2015 documentary begins by profiling the unconventional life of Conor Girard, aka Roaming Bear, a young musician who has eschewed the comfort and security of his upper middle class upbringing to enjoy the "freer-n-finer things in life" as a vagabond, traversing the country by way of hopping freight trains and hitchhiking. More often than not he sleeps under the stars, and frequently resorts to dumpster diving for sustenance.
Shortly after we get a feel for the world of Roaming Bear, we meet his soon-to-be travel companion Mikey, who is about to embark on his first such adventure, with Bear as his guide. Together they pull up stakes from the suburbs of Chicago with their sights set on Olympic National Park on the west coast of Washington. Their shared journey comprises the bulk of the film, and once we are fully immersed, a multi-textured and endearing story unfolds as we meet their families, their friends, and many colorful strangers along the way. Initially, the filmmakers seem to be simply romanticizing the itinerant lifestyle, but as the story progresses, they show us moments of self-doubt from both travelers. Through both confessional scenes and observed conversations, we're given direct insight into how they each process the blessings and uncertainties that come with such a life.
The fact that they both come from a relatively privileged upbringing, with a family safety net still in place, makes for a noteworthy irony: the boring, safe, ordinary life they sought to escape is also what makes it possible to take on such a risky journey, knowing that if they want out, they can have a lifeline thrown their way. That this point can be made softly without making us think any less of them speaks well to the filmmakers' skill in crafting this narrative.