On the road: stories from an American adventure
Part One: The American Dream
Mission Street is where it all began. Stepping off the train in Frisco’s colourful Castro district one Friday in June, I was overcome by a colourful mix of street vendors, taquerías, and a blazing summer heat. Whilst Castro could be mistaken by some for a Mexico City neighbourhood, there was a distinctly American feeling in the air. An air of freedom and of opportunity. The American Dream rages on. And what an adventure it would be.
As I climbed up 19th Street and headed towards the house of a close friend from college, I caught my first glimpse of San Francisco’s magnificent skyline whilst crossing through the manicured Mission Dolores Park. Cast before the bright blue sky, the beautiful skyline hit me hard. It’s all happening. My excitement ramped up and the view was truly something — it’s the kind of view that, when looked at long enough, gives you an immense sense of confidence and self-assurance. You can do anything.
San Francisco is a relatively low-rise city. Other than a cluster of skyscrapers in Downtown, local planning policy has purposefully kept the city low-rise to preserve its unique charm. Whilst some applaud this move, it is not without its costs: housing for many has spiralled out of reach and rents are some of the highest in the country. Dominating the skyline is the city’s newest addition, the Salesforce Tower, whose elegant form serves to draw the eye towards the bay and afar.
The weekend, like the city in which it was lived, was intense and amazing. Between swims under the Golden Gate Bridge and parties on the 40th floor of a downtown high-rise apartment, I explored the city’s rich culture, took in vivid murals and spent time with some amazing people. The city, like so many other places in America, has a powerful sports culture which penetrated throughout. Monday, after pre-gaming with a pretty fun bunch of guys who were all interning in the city that summer, was spent at a Warrior’s rally where thousands of San Franciscans flooded into the streets to chant ‘Go Warriors.’
Before I knew it though, the weekend was up and it was time to head further East. A line had been traced on the map from SF To Denver. All that was left was to take it.
After almost missing my flight due to a series of events which I won’t go into here, I breathed a sigh of relief when the plane finally took off the tarmac and we shot through the air 38,000 feet above sea level. Following a brief layover in Vegas, I made it to the Mid-West for the first time and spent four excellent days attending a conference where, along with a few dozen other young people, we discussed and debated many issues relating to economics, philosophy, and personal development. Already — the trip had been a success.
Part Two: On the Road
From then on is where the real adventure began. I had always wanted to road-trip across the USA. To criss-cross the country as Kerouac had done so many years before me, and to get a sense of the real America that so few people ever got to see. There was one problem: I don’t have a car, nor do I have a driving license. One option was the bus, but that was both expensive, boring, and wouldn’t allow me to truly achieve what I wanted to get from going on the road. The other option was, of course, to hitchhike — and that’s exactly what I did.
Whilst many people warned against it, a friend of mine had recently hitched about 300 miles worth of rides throughout southern Portugal, and it showed me it was possible. Then there’s the fear of serial killers or theft that dissuades most people. Though a quick Bayesian analysis of the situation convinced me it was pretty unlikely and that most people are actually not serial killers.
So leaving early one Sunday morning, I trudged over to the highway and set off out of the great state of Colorado. One thing about America is that the country is truly immense. Just Denver itself took over three and a half hours to walk across in order to get to the highway. Without an automobile, you’re well and truly stuck. Though I was in luck: within twenty minutes of being stood on the highway, a kind gentleman picked me up and dropped me approximately 60 miles down the highway in the direction I was trying to get to. I’d done plenty of research and so knew the spots where I was most likely to get rides. And from there, I was in even more luck. Barely had I put my bag down that an incredible woman, who herself had lived a great share of adventures, pulled over and told me she was driving all the way up to Nebraska and would I like a ride.
And what a ride it was. Gliding through the beautiful Colorado plains, snow-topped mountains in the background, we spoke non-stop about the American experience, discussed what it means to live, and shared stories from our travels and adventures. It felt that I had barely stepped into her vehicle that we had already crossed the border into Nebraska and the sun was beginning to set. Our energy totally resonated, and I wished at that point that she were going the whole way.
Though sadly it could not be, and after that amazing ride, I was back on the highway — the great expanse of America before me. There was tarmac; there were cars. What completed the equation and got me from A to B is a mix of confidence and a belief in the goodness of individuals. That is not to say that success came instantly though. As sun turned to moon and the minutes ticked away on my watch, the prospect of me staying the night in this tiny Nebraska town of 2000 looked increasingly likely. It would not be, however.
Just as I was about to give up, I approached a driver who had stopped and asked if he was heading towards Illinois. By some cosmic coincidence, he replied that he most certainly was and, after a weekend hiking in Colorado, was just driving back to his home in Chicago. I was exhilarated, and although it took me a couple of minutes to convince him that I was great company to drive with, it would be a great ride. We shared our stories and the driver, who I will call Conrad, told me about his love for nature and how he had, over the course of his lifetime, run five marathons and counting. Although by that point my eyes struggled to stay open (it was around 11pm by that time), he told me some pretty incredible stories about his journey to America and what it takes to run marathon after marathon. The mind is absolute.
We crossed a great many states that night — including the entirety of Nebraska and Iowa. As I woke up that morning, the dawn of a new day gleamed before me, and we had already entered Illinois. Before I knew it, Conrad wished me goodbye and dropped me off at a Chicago METRA station, where for $5 I completed the first part of my trip and had arrived in the Windy City.
Part Three: Windy City
Chicago was a dream. Big, busy, and bold, the city truly epitomises everything that America is — the good and the bad. At its core is The Loop, a thriving business district where the entrepreneurial spirit that built the United States continues to live on. Chicago is a place for thinking big, for achieving one’s dreams. Its architects certainly did: after the Great Fire of Chicago, it was carte blanche for architectural experimentation. This led to some of the most iconic buildings, including the first skyscraper in America, being built in that city. One building that particularly piqued my attention was Mies van der Rohe’s Federal Center, a modern and sleek complex of office buildings in the centre of downtown. Marina City, Willis Tower, and the John Hancock Center were also glorious to look at. Chicago has found an ingenious way to keep the city clean and to keep waste out of sight, due to a network of service roads and underground streets that channel through traffic under our feet. It’s an example of excellent urban design and architecture.
I stayed in the city for one full day as I wanted to see all the sights and get a true feel for it. Putting my bags down at a moderately priced but beautiful hotel on the City’s Near North side, I trekked out and spent the next day and a half visiting Michigan Avenue, the Gold Coast, the Loop, Navy Pier, and Lake Michigan. The mouth-watering pizza I bought that night at the suggestion of Lonely Planet’s Chicago guidebook was a welcome change from the rather unhealthy food had eaten over the past twenty-four hours. On the road, there aren’t too many choices.
Part Four: Freedom
The next morning, refreshed and ready to hit the road again, I set off and rode the train down to Gary, Indiana — thinking it would be a good place to get rides out East.
It was a pretty good place — I got a ride relatively fast — but the first person who picked me up told me I was insane to be standing in that town and that it’s not somewhere I would want to be after dark. Lesson learnt — I guess? He left me at a service station a couple of highway exits along. By that time, it was already about three o’clock and I felt a little tired from the many many kilometres I had walked the previous day.
Having been rebuffed by a man driving a big black SUV, I was a bit annoyed and sat on a bench outside the 7/11, drinking a slushie and resting for a while — unsure of what would follow. Though once again, I was in luck. A truck driver who had been having lunch told me he saw me, thought I looked stranded, and wondered if I needed a ride anywhere. I replied that I wasn’t stranded per se, but was travelling across the country and trying to get to Washington DC as soon as possible. He agreed to take me as far as he could, and before I knew it, we were off!
The truck driver, who I’ll call Kenneth, explained he was heading all the way from Chicago to Buffalo, New York, and had driven trucks for the past decade or so after his time in the Army and police. It wouldn’t be the first soldier turned police officer I met — someone with exactly the same background picked me up later in Pennsylvania.
We had a great time driving across the country. The heat was still blazing outside, and the sky was perfectly blue — not a cloud in sight. As we rumbled on through the state of Indiana and later Ohio, I saw the landscape slowly changing, becoming greener and more mountainous as we went through. Ohio felt like it went on forever. It was field after field after field. And though it’s become common to make jokes about ‘flyover country’ (even I do it, lol), contemporary America would not be possible without these great expanses which go to feed the country.
Throughout the ride, Kenneth and I chatted about everything — life up in Illinois, plans for the 4th of July weekend, American politics, all the different states he had visited, people he had met, and so many other stories. He was a great companion to drive through the state of Ohio with. The truck was also immense — I’d never been inside a semi-truck, though it was extremely large, with two beds in the back, a fridge, and even a microwave.
The sun had set by the time we got to Cleveland, Ohio, and so I only got to see the city by night. That whole region continues to have a lot of natural beauty — with lake Erie, snowy mountains not too far, and great forests and landscapes. Though politically, there are reforms to be made. Cleveland, Detroit, and the whole chain of cities sometimes called the ‘Rust Belt’ had their best years around a century ago, when American manufacturing was king and people flocked from across the world to be a part of it. Though globalisation, restrictions on immigration, high taxes, and bad policy has led to a stagnant or even declining population in many parts of these states. The very thing that made these cities prosper, the manufacturing of the automobile, also led to their decline as people gained the ability to move to the suburbs more easily. Though all is not lost — these places continue to be well connected, have good infrastructure, and belong to one of the greatest economy on earth.
After spending the night on the top bunk of the semitruck (whilst stopped — of course), I waved goodbye to Kenneth in Erie, Pennsylvania, and there began an epic three-day trek through that enormous state.
Though it was Thursday, the plan was still to go to DC where a close friend was doing a great internship that summer. It seemed possible — it was about a 7-hour drive and it was 10am in the morning. The first few rides went by quickly — first down I79 a couple of exits with a self-identifying Christian who told me he’d studied economics, started two businesses, and hitchhiked three times across the country in his twenties. I would have loved to speak to him further, but he was only driving locally and had already gone far out of his way to drop me off.
Northern Pennsylvania can be described as a luscious green place full of forests and beautiful scenery. The next ride came very quickly and was another Pennsylvania native who’d agreed to drive me a little further down the highway. When you’re hitchhiking, you always want to be careful not to accept short rides if you’re in a great spot and it would bring you to a very sparse area. Though I had no trouble getting out further down the highway and getting a subsequent ride with a man going all the way to Pittsburgh. He was slightly eccentric — wearing a strange plastic lens under his glasses that made him look like a character from Blade Runner. He told me how he had travelled the world as a photographer and had very fond memories from his travels in India, where he’d evidently had great success with women and once spent three days straight partying with some Parisians he’d met over there. It was a fantastic story.
Another thing that these kinds of travels show you is that truly everyone has their own story and has something interesting to them. Whilst we interact with the universe through our own ego, so does everyone else and it’s important not to discard others and show respect. Doing so can only make your life more enjoyable as you meet others and discover new ways of thinking and interacting with the world.
Arrived outside Pittsburgh, I had a little issue. Three major highways converged, including the Pennsylvania turnpike, and it would be impossible to get onto the turnpike itself at that point. Though without getting onto the turnpike, it would be tough to get to DC that evening. I had to find a way across the city as soon as possible. Thankfully, a woman stopped shortly after I stuck out my thumb and said that whilst she was driving home from work, she could drop me anywhere. I had no idea that it would take two hours to drive across. First, I accidentally told her the wrong highway as I’d read ‘Washington’ on a sign and mistaken for Washington DC, when it was referring to Washington, Pennsylvania. Having realised at the last minute, she said it was fine and that she would drive me across to the right highway. Though arrived at that highway, the ramp was terrible and had construction work going on, so it would be very difficult to hitchhike there. Again, she agreed to drive me further up. Though by that point the woman, who’d only recently moved there, got lost herself and we spent two hours navigating the city trying to find the right on-ramp. Whilst I got to see the city and the famous point where the three rivers merge, the likelihood of reaching DC by dusk seemed to be slipping away like sand through my fingers.
And before I knew it, after the final ride of the day with the aforementioned other ex-soldier turned police officer on his way to go fishing, I found myself stuck in a tiny Pennsylvania town off the turnpike. Try as I might, I stood three hours trying to get out of there — but there was no-one and those who did pass never stopped. At that point, I was faced with a choice — either sleep under the stars, or sleep in the town’s only motel. I tried the former, but quickly decided to shell out the (outrageous) $100 for the motel room.
The next day, there didn’t seem to be much more of a possibility that I would get out of that town. As I stood by the highway for 10 minutes, I felt a drop of rain and could tell it was going to pour down all day. So I quickly ran into a small diner, and that very second, a loud thunder of torrential rain erupted from outside. I thought I was well and truly stuck, and I had no desire to stay in Donegal, Pennsylvania for another night.
In times like those, it may seem evident to give up and find another way out of town. Though the reality is that even if I had wanted to take a Greyhound out, there was not a single public transportation option within 200 miles of where I was, and there certainly weren’t any taxis. And besides my situation, I felt the great sense of freedom, youth, and adventure pulsing through my veins. I knew that I could do anything, that I’d already made it that far, and that the boundless road still lay ahead.
I persevered, changed my tactic, decided to ask people at the gas station as soon as it stopped raining for a bit, and was in luck: the first person I asked told me he was going all the way to Harrisburg, PA, and could drop me off there. I sure was happy to be out of Donegal, no-matter hour beautiful the landscape beyond looked from that quaint town. Hopping in the car, I arrived in Harrisburg a few hours later, having completely bypassed the rain and bad weather. Like all of America it was a wonderful drive, winding through the mountains on that endless road.
I blasted Foxygen’s ‘On Blue Mountain’ through my headphones whilst literally driving through Blue Mountain, Pennsylvania, and once again felt the energy and life of the road throughout my body. It’s in times like these that one can truly understand what Dean Moriarty means by IT. Some other great tunes and artists from the road include Leon Bridges’ amazing soul mixes, Omar Apollo’s newest singles, and a whole mix of other pop, R&B and indie singers.
Arriving in Harrisburg, I was so close and knew it was possible to make it in a couple of hours. By that point I had shifted my goal to New York City, where another friend was spending the summer whilst interning in the City. Though again, after getting two short rides to the other side of town, I had no luck and waited endlessly at a highway intersection. At times, it felt frustrating waiting. Why is no-one stopping? I look clean and friendly. What is the problem? Though as soon as I got annoyed, I remember that I had chosen to do this and that it was all part of the great adventure. It’s the uncertainty and accompanying opportunities that make it interesting.
My theory is that people are just more cautious on the east coast. At a highway rest station, I asked a couple to drop me one exit further as it was a better place to catch a ride, and they asked to see my ID and bags. This was, of course, fine with me, but it provides further evidence in favour of my theory. It’s both a symbol of the tremors that have spread throughout the United States in recent years and a sign of the growing distrust that Americans now have towards one another. It also reflects a shift towards a general increase in the aversion towards risk. The risk of homicide or theft has statistically not gone up, but people’s perception and fear of these incidents have, perhaps induced by the 24-hour news cycle and social media algorithms which promote negative events to keep the publics’ eyes glued to their screens for longer. It’s only gotten worse since covid, when people greatly overestimated and feared what was for most a very small threat. I personally think it is a shame and that life’s most precious moments come from stepping outside one’s comfort zone.
One thing I considered is that I was just in the wrong spot. The highway ramp where I stood was quite quiet, and I reckoned there was a greater likelihood of being picked up if I walked back one exit where a large truck stop and gas station was located. At about 6pm, I therefore picked up my bag and began the hour long walk to the next exit, crossing through tall fields, tranquil forest, and past big family homes. It was pretty incredible that whilst millions of people drove past this side of America each year on the nation’s busy highways, almost nobody left to explore what lay beyond. I did explore though, in what was a very peaceful walk. That night, I once again stopped in a motel, 200 miles out from my destination. I was so close yet still so far.
Saturday would be the day in which I got to New York City. From Harrisburg, I quickly got a ride out to Allenstown where I knew that worst case scenario, I could always get a bus later that day. From Allenstown, I got a number of short rides across town, then someone offered to drop me right on the border of Pennsylvania, in Easton. Knowing how close I was getting, I accepted. 100 miles and 1 hour and a half from New York City, it felt to me as if I could almost reach out and touch it. I also knew that the final ride would have to go from PA straight through New Jersey since, for some bizarre reason, it’s illegal to hitchhike in NJ.
Thankfully, it didn’t take long to get that final ride. Having waited approximately 30 minutes, a Dominican pulled over and I dashed towards his car. I was overjoyed when he said he was going to Queens and could drop me in Manhattan on the way.
Seeing the Manhattan skyline emerge from the New Jersey turnpike was like crossing over into heaven. At that point, I knew I had made it and had reached my goal. The feeling was unbelievable. Hopping out his car off 42nd Street, I thanked him (more grateful than he could ever know) and dialled my friends to meet up. I was in Manhattan, the greatest city on earth, and my time on the road was over.
Despite all the warnings that hitchhiking was no longer possible, I had done it. A smile beamed off my face, both from being in the city and from that great sense of achievement.
Being on the road is one of those moments where you’re hyper-aware that there is no manual to life. There is no-one to hold your hand. No-one to tell you where to stand or how to approach people. There’s no punishment for withdrawing from others or being afraid. All that happens is that you stay where you are and make no progress. Going on the road forces you to take responsibility, to find creative ways to solve problems, and experiment with different techniques. It’s an experience that you can only grow from, and despite the long waits and uncertainty, I have zero regrets. I truly believe that everyone should do it at least once.
Part Five: goodbye for now
The last few days have flown by. New York City is one of those places that is impossible not to love. Despite some of the crazy people, the rats and constant noise, it’s a place of opportunity, of life and of exploration. When in Mexico last year, I wrote about how the American Dream still exists if we simply reframe it as the search for opportunity and adventure rather than an impossible consumer quest. This mad journey has only served to confirm this.
The weekend was splendid, spent with the best people and in the best places. On Saturday, joined with my best friends from SciencesPo, I walked across the Brooklyn bridge where together we had lunch at the TimeOut market and watched the sunset. Monday was the 4th July and I headed over to DC that evening for two days in which I got to visit the Capitol building and ate some great food. A certain friend, on whom I can always count on to have fascinating discussions, and I caught up over coffee this morning, then I walked over to the UN building where another friend (and future roommate) toured me around. It was a tremendous way to end this great American adventure.
As I write this, I am gliding thousands of feet above the Atlantic back towards Europe where another set of adventures await. For now, it’s à la prochaine, to you, America. I can’t wait to see what the future holds in this magical land.
Note: names have been changed to preserve the person’s identity.
