What Kerouac’s Wilderness Teaches Us About Parenting

On the third day of our mother-son road trip in Northern California, Scout and I stare each other down in the parking lot of Mount Tamalpais State Park, near the Pacific.

We’re hot, tired, and hating each other.

That last part’s not true. We love each other.

But the heat, Scout’s stinky feet, and my excessive nagging make us edgy. He reacts by shutting down; I react by asking why he isn’t showing more enjoyment. If this continues, we might start shouting.

Then, out of nowhere, angels.

A father and son, twin-like in their resemblances to John Travolta. They pull alongside us in a carbon-belching Volvo. Stepping out and addressing me, older Travolta practically sings, “What a day! My son and I are on a father-son road trip! We just did Tomales Bay. You ever done it? If not, you should!”

I beam congenially at him, but my competitive spirit has ignited. “How weird that you’re on a father-son trip,” I say. “Because we’re on a mother-son trip!” Then, to myself: But ours is amazing. Because we’re not just on a trip, we’re on a pilgrimage.

Our journey stems from a book I read and loved and gave Scout just after his 15th birthday: The Dharma Bums, Jack Kerouac’s classic Beat Generation novel, published in 1958. It tells the semifictional story of a merry band of society-shunning writers and the beautiful friendship between Ray Smith (who represents Kerouac) and Japhy Ryder (the poet Gary Snyder, whose work I worshipped). Japhy teaches Ray about Buddhism, hiking, mountain climbing, and how to become a fire lookout. (Full disclosure: It also contains plenty of R-rated events, but since Scout has watched his fair share of Game of Thrones, I thought he could handle it. Plus, it generated a lot of conversation.)

After reading the book, Scout had this assessment: “It adds spirituality to the things I love doing. You know, hanging out, backpacking.” He then said that he’d like to visit some key places Kerouac details in the book to see if Dharma Bums spirit still exists. I wanted to do a trip with Scout, because in kid-rearing, time speeds up exponentially the second they hit high school. And it’s hard not to worry about the limited opportunities left to share what you think are the greatest beauties of the world before you blink and they graduate.

Now 16, Scout is a quiet, creative, endurance-sport-loving, mandolin-playing—and worried—kid. His lesser concerns focus on why he can’t ski race faster and if his younger brother will get his driver’s license before he does. He is happiest on weekends, when he’s at home, running on the dozens of miles of singletrack winding through the woods in our small Colorado town. But what keeps Scout up at night are questions about his future. He wants to excel physically and academically, have friends, and enjoy life. In other words, he’s like most kids.

But ever since he was young, people have said, “That Scout. He’s on his own planet.” They usually follow up with, “I wish I could be on Scout’s planet.” For instance, he’s a little Elizabeth Gilbert’s Last American Man in his sensibilities and wishes. Among his favorite pastimes is dreaming of the gaiters he’ll hand-sew before whipping up some elk-meat pemmican to gnaw during the solo climbing trips he’s planning in the Himalayas.

As you might imagine, not all that many kids share Scout’s exuberance for such activities. And there are times when I question my husband Shawn’s and my choice to raise him with such an outdoorsy, Emersonian aesthetic. We put prime importance on outdoor sports and self-reliance. We live inside a national forest. We love it when our neighborhood bears leave paw prints on our pickup. We worship the natural world and worry about the environment. So does Scout.

Which is all the more reason to go on a Dharma Bums adventure. I’m acutely aware that this could be the last mother-son trip we ever do. Substantiating my hunch is the fact that our friends recently invited Scout to work on their fishing boat—in Alaska—next summer. That has heightened several existential questions: Have I set Scout up for the best possible adulthood? And: What if I haven’t? And: If not, what can I still do?

A road trip retracing Kerouac’s steps, from San Francisco to Berkeley to Marin County and on to Yosemite, with some city exploration, hiking, climbing, and camping along the way, just him and me, is at least…something. We planned a week at the end of July, shortly before Scout would start his junior year of high school.

After meeting the father-son Travoltas, I felt a renewed sense of the coolness of our journey. Scout seemed to as well. We were, after all, about to start the first hike we’d ever done with a trailhead at the top of a mountain. From the parking lot, we walked down, to the ocean.

Our first night in California, we walked the North Beach district of San Francisco. The stars were out, and a cool breeze blew in from the Pacific. We headed toward City Lights Booksellers, on Columbus Avenue. Lawrence Ferlinghetti founded City Lights in 1953, and it has long been a home for writers like Kerouac who pushed social norms.

I was older than Scout when I fell in love with The Dharma Bums. I picked it up in my early twenties, during my second attempt at college. When I found the novel, I connected with Ray’s hobo aesthetic and hunger for spiritual seeking. But the narrative I loved most was the one in which Japhy springs Ray from the “grooming schools for the middle-class non-identity” and takes him “prowling in the wilderness” on a climb up Mount Matterhorn in the Sierra. I hungered to find “the ecstasy of the stars,” like they did, and I marveled at how someone as inexperienced as Ray could so easily get deep into the wilderness under Japhy’s tutelage.

Once they start hiking, Ray is overcome with childlike amazement. But a hundred feet from the top of Matterhorn, he aborts the mission. “The whole purpose of mountain climbing to me isn’t to just show off you can get to the top,” Japhy says. “It’s getting out into this wild country.” Scenes like this, and Ray’s calls for a “rucksack revolution,” in which “thousands or even millions of young Americans” take up wandering, allegedly inspired just that. Even cooler, 60 years after The Dharma Bums was published, the book is inspiring Scout.

Now at City Lights, we lounge in the Poetry Room, scouring Beat-related titles. When it’s time to cash out, Scout expands his Kerouac collection, plunking The Dharma Bums precursor, On the Road, onto the counter.

After touring the Beat Museum and walking Kerouac Alley, we head to Berkeley, where we see the ghosts of homes where Kerouac and Snyder once lived, we stand on the exact location of the Free Speech movement’s birth, and we score two scalped tickets to see Scout’s favorite soft-political, barefoot, ukulele-strumming crooner, Jack Johnson, at the Greek Theater.

But soon, city claustrophobia sets in, so we head to Mount Tam to hike.

As we drop down the trail toward the bright blue Pacific, a Dharma Bums word pops into my head: compassion. As in compassion for everything, what Ray strives for in the book. I’m not going to pretend I have any real understanding of what this means. I bring it up only because, having just read about it, I feel it for Scout as we walk toward Stinson Beach. We’re on the Dharma Bums trail, yet he still seems out of sorts.

I get his sometimes unexplainable descent into despair. Another reason I conceded to the trip is because it’s so hard being a teen. It feels obtuse to list all the challenges today’s kids face, so I’ll highlight Scout’s personal list: disappearing snow, vanishing coral reefs, the island of plastic in the North Atlantic, and not knowing where he “fits.” That last item hits me hardest, because I know how hard it has always been for Scout to believe he fits in.

It’s been top-of-mind ever since we departed for our trip.

But I’m kind of speechless when I ask him what he wants to be when he grows up, and he replies, “Honestly? A pirate.”

“Ok. What else?”

“Cowboy.”

“Or…?”

“Writer.” (Shit.)

But he also lands on slightly more dependable career choices, informed by his childhood: Forester. Mountain guide. Outdoor educator.

After we reach the beach, we snack on oat bars and Scout body surfs. Then we hike back to the parking lot of Mount Tam. Even though it’s approaching dusk, we decide to hightail it to the Sierra Nevada, where we’ve planned a multiday backpacking trip. It’s not to Matterhorn Mountain—too much snow—but the Quartz Mountain Trail, which accesses a gorgeous chain of lakes just inside the Yosemite’s southwestern boundary. Scout is navigating.

“Can you ask Siri to help?” I ask as we hit the highway.

“Sure, Ma,” he says.

“Then why aren’t you?”

“One sec, Ma.”

Instead of doing the easiest and most accurate thing, he types “Yosemite” into MapQuest. Then he tries to zoom in on his cracked iPhone screen and navigate us there himself. It leads to hours of lost time we could have used to find a campground close to the park. But unpreparedness makes us more bum-like. We drive until hallucinogens of leaping deer make me pull over, and then we hastily set up camp—inside our rental car. It’s amazing how comfortably two adult-sized people can sleep fully stretched out in a Toyota Yaris. We get a solid five hours before waking up and heading to Yosemite.

Thanks to Scout’s navigating, we approach Yosemite from the west. The Quartz Mountain Trailhead is on the far southeastern side, so we have to drive through the park. We arrive and find it clogged with motorhomes, tourists, and iPhone photographers shooting towering rock.

Still, I’m happy we are driving through, because anyone who knows Scout knows that he should have been born during the golden age of the Yosemite Camp 4 dirtbag climbing revolution. Yet seeing as he is the tiniest bit passive, he only quietly mentioned, when we were still in trip planning, how vitally important it was that he visit this holy site. Scout did bring his climbing shoes, which I assumed he’d use if we found some choice granite, and now that we’re in the park, with the option to go to Yosemite Valley or continue on to the Quartz Mountain Trail, he wants to drive beneath the granite gods of up-until-now only images in photographs and documentaries: El Cap, Sentinel Dome, and Half Dome.

Approaching Camp 4, Scout shouts, “That’s it!”

I slow the car. We see it. We need to get going.

But at the intersection that will eject us onto the highway leading to the Quartz Trail, Scout asks, “Can we go back? I mean, I don’t want to mess with the schedule. It’s just…”

There’s no question. Something is different in Scout. I see it.

He hasn't shown this kind of excitement yet on our trip. All of a sudden, inspired by the enormous, gleaming walls of El Cap and the vision he has of himself one day climbing it, Scout takes the moment into his hands.

He jumps out, digs in his pack, and finds his chalk bag and shoes. Then, as I watch, Scout lopes away from the car and into the trees. He’s not going to climb the Nose or Dawn Wall, but he’s letting himself run, disappearing into the distance, where he’ll find a boulder. He’ll let himself climb, forgetting about me and about feeling uncomfortable and about his future. And when he returns, he’ll be flushed. Flushed with something that’s only his to name, but it’s clearly a new emotion on this trip, and maybe in his life.

It’s so good that I almost want to end our story with it. But we have one more item on our tick list: our backpacking trip to Chain Lakes. We bid goodbye to the park. We start our hike. And something has changed.

All the way to camp, Scout leads the way. When I start to feel down—because I do, letting myself churn over the scary world awaiting my son—he elevates me in the same way I try to elevate him. When we get to the first lake, I'm tired, so Scout sets up camp, cooks, and then sits with me, looking at the water.

There’s an island out in the middle, shaded by trees and dotted with boulders. Features on the island are reflected perfectly in the water. As we stare, Scout says, “There’s the thing, the reflection of the thing, and no thing.”

I don’t know if this is right, but it sounds like a Japanese koan, a riddle or puzzle Zen Buddhists use to untangle truths about the world and themselves.

It must be something he picked up from Japhy or Ray, who are literally here with us. I lift them out of my pack, and we read a little Dharma Bums before drifting into a soft, quiet, wilderness-induced sleep.

The next morning, neither of us feel like staying here, because we were so jazzed by the last place. First, we hike to a lake, and I watch Scout leap from enormous glacial rocks into the Sierra snowmelt–filled water. We sit together, eat lunch, and then pack up and leave. We hike out, returning to Yosemite Valley and the moment where Scout embraced his power. We head to Camp 4 and climb for a good long while to the top of Yosemite Falls.

There, standing beside Scout and looking out onto the gleaming valley, I can almost see his future.

Tracy Ross is an NMA award winning writer, author of The Source of All Things. She lives with her family at 8,000 feet in the mountains above Boulder, Colorado. Dylan Fant (@dylanfantillustration) is an illustrator living in Burlington, Vermont.