The sun-bleached semitrucks began to drag and shift towards the right lane as the road inclined. I sped up the narrow highway into the dry California hills, then down into a bare valley. An ancient Air Force base sprawled far off to my right and flocks of tumbleweeds huddled in the median on my left. The twilight sky was baby blue and the baked road a light mauve, the colors of whimsical nostalgia, like a ’50s diner. I was chasing the remnants and pockmarks of Route 66.

In popular imagination, road trips are a powerful matrix of freedom. Endless roads, sprawling prairies, and, if traveling by motorcycle (or so I hear), “the wind in your hair and the bugs in your teeth.” You can turn down just about any road and stop just about anywhere.

I had recently been spat out of college and into the “real world,” where freedom apparently abounded. But, a little reluctantly, I found myself less interested in claiming this concept for myself and far more in need of attaching myself to something, finding something I could root myself to. For orientation, I chose to trace the final miles of the American pilgrimage to California, to join the decades-long caravan headed west on Route 66.

For as much as road trips have historically been associated with freedom, they are riddled with constraints. You can’t really rule the road – the road rules you, grants you a very finite number of directions in which to travel. There are few activities you can do while driving. If you’re a passenger, your entertainment is confined to what you can do sitting down. If you run out of money, you’re effectively trapped. But the association with freedom persists – even when the meaning of “freedom” changes.

In his On the Road with Saint Augustine: A Real-World Spirituality for Restless Hearts, James K. A. Smith picks at the current zeitgeist of what freedom feels like: “We might be surprised by how many people are hoping someone will give them boundaries, the gift of restraint, channeling their desires and thereby shoring up a sense of self. Indeed, there may be a generational dynamic to this, where boomers – whose revolution of negative freedom remade the world – imagine younger generations wanting the same but instead hear those young people asking for the gift of constraint, the charity of boundaries.” As I planned out what side trips I’d take to hunt iconic vistas or desert sculptures, I found the white spaces between the blue roads on the atlas surprisingly comforting, the un-roaded regions I was commanded to peacefully surrender – finally and mercifully, someone was telling me somewhere I couldn’t go, something I couldn’t do.

The theme of freedom is as ubiquitous in American road-trip literature as grain silos are in Midwest speed-trap towns. But what it means is clearly not universal to all times and peoples and places. Frederick Jackson Turner’s “Frontier Thesis” explained to Americans in the late nineteenth century why they were naturally destined to expand, to live on ever-fluid borders at the edge of “civilization.” Though there’s clearly a distinction between roaming national parks in a minivan on spring break and one-way migration via covered wagon, freedom and expansion are also still closely associated. If someone in search of a homestead to farm obtains land at the expense of a native of the western United States, is there freedom in this complex? The settler would likely think so. Those from the regions who found themselves suddenly confined to reservations or forcibly set on the road to Oklahoma Territory would clearly think not. What people think of as “freeing” is sometimes not neutral or universally positive. Martin Luther King, Jr found road trips a fitting example of one of the things that makes “the cup of endurance run over” in his “Letter from Birmingham Jail”: “When you take a cross-country drive and find it necessary to sleep night after night in the uncomfortable corners of your automobile because no motel will accept you….” Freedom must be considered not only as a personal right, but also as a possible condition of a society – if some of us are free and some of us are not, then collectively we are not free. Increased options on one person’s behalf at the expense of others results in no net gain.

In popular imagination, road trips are a powerful matrix of freedom.

This idea of freedom-as-expansion, of burning the existing boundaries, seems to sometimes turn into something closer to a curse than a gift or natural urge on a personal level as well. The “freedom of the road” tried on by Jack Kerouac’s somewhat squalid characters in On the Road or by Christopher McCandless, who traveled into the wild of Alaska to avoid “Society,” ended in disillusionment. Dean Moriarty drifts at high speed through new cities and relationships until he spins out into a void of banal hedonism. Chris McCandless scrawled in his diary, just before he died alone in an abandoned bus, “Happiness is only real when shared.” For those running from themselves instead of to a real place with a real chance of a richer life, the dizzying flight sometimes becomes disorienting, degenerating. Smith muses, “When you’ve been eaten up by your own freedom, and realize the loss of guardrails only meant ending up in the ditch, you start to wonder whether freedom is all it’s cracked up to be – or whether freedom might be something other than the absence of constraint and the multiplication of options.”

By choosing to limit my own road options to Route 66 and looking for the traces of people who had followed it for their own reasons, I noticed that I really felt no lack of freedom. The derelict water parks and spray-painted buses, in spite of prompting some undeserved nostalgia for a time I never lived in, served as good fodder for imagining the families who fled to California’s promised land. Watching the sun set over Joshua trees gave me time to reflect that the Judeo-Christian tradition has been on the road for millennia. In his Faith on the Road: A Short Theology of Travel and Justice, Joerg Rieger observes that if you took out the stories in the Bible that deal with travel, there would be little left. The story of Israel began with Abraham, a traveling emigrant, leaving his home and family. Refugee Israelites followed the path set by a pillar of fire and cloud for decades. It is estimated that Jesus walked twenty miles a day during his ministry in Galilee. Rieger contends that “Christianity is not primarily a matter of pews and buildings; Christianity is a matter of the road.”

The National Park Service characterizes Route 66 as “a symbol of the American people’s heritage of travel and their legacy of seeking a better life.” And many really did find lives that were better in the ways that they hoped. John Steinbeck, in his 1939 classic, The Grapes of Wrath, explained that “66 is the path of a people in flight, refugees from dust and shrinking ownership, from the desert’s slow northward invasion, from the twisting winds that howl up out of Texas, from the floods that bring no richness to the land and steal what little richness is there … 66 is the mother road, the road of flight.”

I finished my road trip through southern California with a few more souvenirs (justifying this miniscule materialism as “embodiment” or a harkening to original Christian tradition of pilgrimage mementos) and a few more questions about what American “freedom” has felt like to those who stood on the outside of it, those who were made into the boundaries to be overcome. I also felt a little more deeply rooted to a long, long tradition of travel, and I learned that freedom can sometimes be found by choosing the right bounds, by acknowledging the constraints of the road.