How A Cross-Country Road Trip Inspired By Kerouac And Steinbeck Helped Me Figure Out My Life

Everyone suffers from an identity crisis or two in their lifetime, and mine occurred when I was 21 years old, about to enter my senior year of college without any clue as to what I wanted to do or where I wanted to go after graduation. I was confused, clueless, and downright terrified about my murky future. Instead of talking it over with my friends and family or connecting with a career counselor, I decided the best way for me to figure out what I wanted in life was to venture out into the world and see what it had to offer. Like I do with my most troubling dilemmas, I turned to my personal library for the answers, and let books inspire the cross-country road trip that helped me figure out just who I wanted to be and where I want to go in life. I had no idea just how much the trip — and the books — would change my life.

It was August of 2011 when I decided to pack a bag full of clothes, granola bars, and a few of my favorite paperbacks and head out, yes, on the road. I had been reading about the adventures of some of my favorite authors and characters since I was young, and it was time for me to have a few of my own. From my bookcase, I pulled down John Steinbeck's Travels with Charley, Hunter S. Thompson's Fear and Loathing is Las Vegas, and, of course, Jack Kerouac's On the Road, and flipped through the familiar pages, mapping out a cross-country road trip based on the places in the books. Each book meant something special to me, and I thought that by retracing the literal steps within the novels, I could shed some light on the literal steps I should be taking. After all, it wouldn't be the first time that these four books shaped a part of my life. Fear and Loathing got me interested in journalism early in my youth, while Travels with Charley inspired me to become a travel-lover. On the Road was the book that convinced me I wanted to become a writer. These novels influenced me throughout my life, and I hoped to tap into the power once again for this trip.

For two weeks, my worn out paperbacks and I climbed on and off Greyhound buses from Boston to San Francisco and everywhere in between, exploring the country and the people in it. If traveling by bus was good enough for Jack Kerouac and his character, Sal Paradise, it would be good enough for me. I used the countless hours riding down long highway roads to reread my novels, make pro and con lists about each city I visited, and write my own story. Instead of crashing in hotel rooms, I took late night buses that let me rest and showered at YMCAs and rest stops wherever I went. It might not have been the most glamorous mode of transportation, but it gave me more than enough time to see the country the way it should be seen: on the ground.


John Steinbeck's Niagara Falls

I departed from Boston, and my travels first brought me north, where Steinbeck's Niagara Falls trip beckoned me to New York state. I was amazed by the sheer size of the beautiful waterfall before me, as well as the magnificent diversity of the people visiting it. There were solo travelers, like me, with little more than a backpack and a bus ticket, big families enjoying the last of their summer vacations, and plenty of young couples holding hands, kissing by the falls. A few couple even got engaged. My trip had barely started, and already I could see that the options for my future were endless. If I came back here again, which one of these people would I be?

I was amazed by the sheer size of the beautiful waterfall before me as well as the magnificent diversity of the people visiting it. 

I only spent a few hours in New York State before heading west, Chicago bound. 

Jack Kerouac's Chicago

Chicago was the city of Sal Paradise's crazy jazz nights, the place where the drinks were strong, the music was loud, and the people were beautiful. The Chicago I found was changed drastically, but you could still hear the faint sound of jazz over the entire city. There were saxophonists in the park, trumpet players by the lake, and I even met a trombone player on Navy Pier. The city I stood in seemed dirtier, a bit sadder, and maybe more broken than the lively scenes in On the Road, but Chicago still had plenty to offer. It was the first city on my trip, and it was a place of art, culture, and diversity — three things I craved badly in my small-town style life back home. I soaked up the sun by the water, took a water taxi to get a better view of the city's skyscrapers, and found a hole-in-the wall pizza place that featured a jazz pianist by the back bar door. The city seemed like the kind of place that, at any turn, you could stumble into a magical place and discover something entirely new. I was beginning to think I had my answer — that city life was for me. But after seeing what Chicago had to offer, it was time to move on. Who knew what else I could find out there.

Steinbeck's Montana

John Steinbeck's travels drew me further west, through Montana where the mountains were big and the towns were tiny. It was the kind of place where you realize how small you are compared to the rest of the world. 

John Steinbeck's travels drew me further west, through Montana where the mountains were big and the towns were tiny. It was the kind of place where you realize how small you are compared to the rest of the world. 

I stopped at a family-run bowling alley that was also a grocery store, bar, and gym, and had a beer while discussing life in the mountains with the elderly proprietor. I was from a small town, too, I told him. Whereas I couldn't wait to leave my hometown, this man hoped he'd be buried in his. Would I miss my old life if I decided to start a brand new one? I wondered if I would miss the place everyone knew my name, because like this man told me, there's no better feeling than familiarity.

Steinbeck's Seattle

Steinbeck's book kept propelling me toward the ocean, so I made the trip to Seattle. I wanted to walk the old port district and see the author's old stomping grounds, take in the sounds, sights, and smells of the public market, and soak up the place where so many creative people, including Steinbeck, have found inspiration. Seattle felt fresh and new. There were a million museums, galleries, and landmarks to visit, but just walking the streets and meeting the people gave me plenty of insight into the city's secrets. Seattle seemed to be the kind of place where city meets country, where metropolitan meets wilderness. The only thing taller than the skyscrapers were the mountains around them, and the ocean seemed to stretch out into a wild and unknown territory. I was finally starting to feel like I had found the best of both worlds. I was finally starting to feel like I wouldn't have to pick between a big city and a small town if I could find a community like I did here. To celebrate, I cracked open Fear and Loathing in Las Vegas, and tore off into the night towards those bright desert lights.

Seattle seemed to be the kind of place where city meets country, where metropolitan meets wilderness. The only thing taller than the skyscrapers were the mountains around them, and the ocean seemed to stretch out into a wild and unknown territory.

Because every Sal Paradise needs a Dean Moriarty and every Raoul Duke needs a Dr. Gonzo, I didn't do Las Vegas alone. Instead, I met my best friend Erika there for her 21st birthday celebration. We stayed in the Venetian, took in some shows, and, of course, gambled our way down the strip. It was a lavish, it was wild, and it was undoubtedly alcohol fueled. It reminded us how young and free we still really were. It was proof that, if you wanted to seek it out, adventure was there waiting for you. And when you were ready to leave, you could watch the neon signs fade in the rear view.

The Beat Generation's San Francisco

From there, I was headed to the city so many, including Kerouac and Steinbeck, had written about: San Francisco. I walked the very hilly streets of San Francisco, venturing into Chinatown to buy souvenirs, stopping off by Fisherman's Warf for drinks and fresh seafood, and exploring the neighborhoods Jack Kerouac and his fellow beats ruled in the '50s. I stopped buy the site of the Six Gallery reading, the very place where Allen Ginsberg first read Howl, and I shamelessly spent over and hour in City Lights Bookstore, where I bought yet another copy of On the Road and Howl. San Francisco was the stuff of my literary nerd dreams, and I soaked up every windy moment of it before getting back on the bus for the three day drive back to the east coast.

I walked the very hilly streets of San Francisco, venturing into Chinatown to buy souvenirs, stopping off by Fisherman's Warf for drinks and fresh seafood, and exploring the neighborhoods Jack Kerouac and his fellow beats ruled in the '50s.

New York City

After nearly 72 hours and four different buses, I found myself back on the coast I started, but in a brand new city: New York. Every author, not just the ones whose books I carried in my backpack, had something to say about New York City. Some hated it, some loved it, but everyone agreed that there was nothing quite like it. I didn't have enough time to truly enjoy all the city has to offer, but I went beyond Times Square and walked through Central Park, Museum Mile, the Upper East Side (if only I brought Harriet the Spy with me!), until I reached the East River and had the city at my back. It felt good to be in a city. It was comforting to be closer to home, and it seemed like all five boroughs were just waiting for me to discover them. 

In the end, I graduated from college and moved to New York City. I like to think there's something symbolic about the fact that I ended my road trip in the place I decided to make my home. But the truth is, my trip didn't give me a clear answer about anything. Instead, it showed me how vast the country is, and how many options I truly had before me. I spent the last year in college using everything I'd experienced to guide my job and city hunt. But if my trip taught me anything, it's that nothing is simple. Life is about trying new things, even if you like the old. It's about being open to new chances, new people, and new experiences. And, unlike the old saying, it's about understanding when to come home, and knowing that you always can.

I like to think there's something symbolic about the fact that I ended my road trip in the place I decided to make my home. But the truth is, my trip didn't give me a clear answer about anything. Instead, it showed me how vast the country is and how many options I truly had before me.

I went to New York, and I loved it. I worked in publishing, and I loved that, too. then, after two and a half years, I left. Because no matter how much I loved the city and my job, I knew there were other things for me to try. Now I'm a writer in Massachusetts, and in five years, I may be an editor in Seattle. I know now that life, at least my life, is meant to be one of continual change and new experiences. 

For me, life will always be better on the road.

Images: Sadie Trombetta

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