Voices from the Road

How a 1992 road trip spurred a lifetime of chasing experiences over comforts

The desire to just “go” was always there in me, buried—yet in motion, building, like magma under the earth’s crust. It just needed an outlet, a time to finally erupt and push me to get on the road. 

During my childhood, the notion of travel teased me nearly every day. I was an Army baby, but my dad got out of the service when I was 2 years old. Thus, I heard my older siblings and parents talk about being stationed in Germany, North Carolina, California, and elsewhere. As if that weren’t already enough, I grew up in an Army post town. So, my Army classmates often talked about their time in Hawaii, Europe, and other great places. 

The one travel outlet I had was my dad’s VW campervan. We camped all over New England, but also took long road trips to see family in Wisconsin, Texas, and Washington, D.C. He put more than 230,000 miles on that camper. 

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So, from a very young age, I was instilled with an unending yearning to go

In college, my dream of “the drive” continued to build. Magazines like Smithsonian only fueled that fire further with stories about unique, out-of-the-way corners of the U.S. By my high school senior year, many of my classmates talked about taking a big trip to Europe. But while they looked east, I was looking west. 

four people with their hands on their head in front of a mountain overlook

Flights and hotels were well out of my means, but I knew I could drive. I did have a car; my dad’s old VW Golf with about 90,000 miles on it. Further, we have a big, wide, diverse, miraculous country and I wanted to see it—the Colorado mountains, the California Coast, the architecture of Chicago, museums, public lands… I wanted to touch them, taste them, smell them, feel them. I couldn’t wait. 

As summer began, I went to work. I took a job as a bouncer, then found work as a local reporter for a regional paper. I lived for another year in my mom’s house and saved my pennies. 

Reminiscing on the ‘90s

Planning a trip like this in 1992 certainly wasn’t like it is today, when everyone has access to online trip planning resources. I did three key things in those pre-internet days. 

First, I called AAA. As a member, I knew I was eligible for free state driving guides, and I asked for them. The woman on the phone said, “Sure. Which ones do you want?” I replied, “All of them.” A week later, a big box arrived, filled with 50 state guides. 

I also wrote (an actual, stamped letter) to the editor-in-chief of Smithsonian Magazine. I never thought he’d reply, but, inspired as I was by their stories, I had to at least try and ask his advice on where I should go during this rambling road trip. 

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Not only did he reply, but he circulated my letter to the entire editorial staff and each one sent a sheet back with a short list of suggestions, often with notes like “Sounds like SO much fun!” and “I want to go too!”

a typewritten letter on smithsonian magazine stationery

I also joined American Youth Hostels. In the country, I knew I could camp. But in cities, I’d need some lodging options and AYH was the answer. I added their national hostel guidebook to the box of state guides.  

Headed west 

Finally, after a false start or two, I woke up one morning and told my mom I was leaving. I pulled out of her driveway, drove through my central Massachusetts hometown, and hopped on Route 2, headed west. 

I started ticking off sites and attractions: Fort Ticonderoga, Cooperstown, Niagara Falls, and other sites in New York. I cut through Ohio, and I settled in for a few days in Chicago, tearing through museums and soaking in the city’s incredible architecture. Up next was St. Louis, where I stayed in a Noah’s Ark-themed hostel, toured the Budweiser bottling plant and fabulous botanical garden, and met a farming couple who’d been displaced from their homes by recent flooding. I then blazed through Missouri and Kansas in a single day, eager to get to the Rockies.

In Colorado, I hiked Rocky Mountain National Park, met a woman who was there for a belly dancing workshop, checked out ghost towns, explored Aspen, had a few fantastic days at Mesa Verde National Park (complete with all-you-can-eat pancake breakfasts) and, in the process, learned a little something about altitude sickness. 

I settled into a pattern of driving for a day, then enjoying the next destination for a few days. I was spending about $20 per day (it was 1993 after all), most of it on gas. I rarely ate out, instead heating cans of Chef Boyardee beef raviolis on a camp stove.

After Colorado, I pressed onto Reno, Nevada, to visit high school friends working at hotels there. I crashed on their couch and was quickly introduced to the most, ahem, “cost effective” joints in the city. From Reno, I spent time in Yosemite, then went on to San Francisco, California. I learned the hard way that the city’s ample hostels booked up at least a year in advance and spent a rough night trying to sleep in my car. Undaunted, I set my sights on Pacific Coast Highway and a beautiful hostel that was an old light house. 

I drove that iconic highway with a smile on my face, hitting long-imagined spots like Big Sur and Hearst Castle. A few days in San Diego allowed me to see more high school friends; one of the benefits of going to a school filled with military kids is that they often disperse all over the country after graduation. There were adventures in the Grand Canyon; more high school friends to see in Phoenix, Arizona; family in El Paso, Texas; and one last stop in San Antonio, Texas, where I enjoyed the River Walk amid the fabulously coiffed attendees of a hairdressers’ convention. 

I then beelined straight to Washington, D.C., sleeping in my car (or trying to) one last night in Arkansas. I arrived in D.C. ready to move into a house with two college friends and signed a lease the next day. 

My entire budget for 2.5 months on the road was about $1,800 (again, in 1993 dollars). 

I’m proud that I made the decision, at that point in my life, to hold off on starting a career and making money, and instead get out to see just a bit of this big, miraculous country—and to do it alone. It was that spirit that eventually led me into travel writing, a field I’m still in, having eschewed a lifetime focused on securing comforts for one built on immersion into tangible, often amazing, even story-worthy experiences. 

Chez’s road trip

Meet the Roadtripper

Chez Chesak