Celebratory Adventures: Three Generations of
Cross Country Road Trips
To tell this road trip story appropriately, I’m enlisting two other authors: my father (who now goes by “Grandpop”) and my daughter (who I call “kiddo”). Together, we three make up the crew who took cross country road trips to celebrate our graduations.
Yes, you read that correctly: three consecutive generations of my family celebrated their graduations by taking cross country road trips! To a certain degree (dad joke alert!), it makes sense. My passion for road trips came from my father, and it was natural for me to pass that love on to my daughter.
GRANDPOP: My son is right – I’ve always loved to travel. I have a lifelong passion for road trips. The first one occurred in 1960, when I was 12. My parents flew us from Maryland to California, and we drove to several other western states. It was an incredible trip and I fell in love with San Francisco and the West!
At age 18, immediately after graduating from high school, I drove around the perimeter of the United States, even venturing into Canada and Mexico. My cousin Eddie and I were on the road for 47 days and 47 nights: 8,500 miles in Eddie’s Oldsmobile Cutlass. The trip of a lifetime!
Take Back Roads:  I struggle with how to best frame this story: do I start at the chronological beginning, with my father’s trips? Or do I start with my own trip and the paradigm-shifting experiences I had on it?
I think I’ll start with something that happened much more recently. Something that isn’t directly related to any of our three generations’ celebratory trips.
My father came to visit us in California this August. It was the first time that any family member other than my kiddo had come from back east to see our new home.
Anyway, it was my father’s first night in California, and we three (my wife, my recently boomeranged daughter, and myself) were hanging out with him in his hotel room as he was getting settled in. He was sober – we’d had drinks – but he was in the grandest of spirits. Spinning yarns, boisterously laughing, and generally doing a great job of being the free-wheeling center of everyone’s attention. He was completely free of from being reined in – sorry mom! – and had naturally settled into the role of entertainer.
He talked very openly that night, completely impromptu, about his cross-country journeys so many years ago and how they impacted him. It was a very poignant moment for me, because for the first time in quite a long time, I felt like I could completely understand and relate to my father.
That’s how powerful these cross-country journeys can be, when you’re able to be open to the experiences that they have to show you.
Grandpop: That night, I felt closer to my son, daughter-in-law, and granddaughter than I have ever felt. And I was in awe of their courage to make the cross country move they did.
Kiddo:Â Â And looking back on it, this once in a lifetime experience (now twice!) left me with so much life experience that I feel confident to travel on my own … and even to move cross country myself!
Also, having that significant amount of time with my father has been very special to me.
Since he moved to California, I only got to see him maybe once per year, for about a week or so.  Getting to spend every second of our cross country road trips together led to amazing conversations and getting to know my father better!  If I have kids in the future, I want to continue this tradition and take our own cross country road trips together!
Driving Cross Country in the 1960s
TBR: Now feels like the appropriate time to tell the tale of my father’s epic cross country road trips, taken smack in the middle of the Age of Aquarius. Yes, that’s right: He was actually in San Francisco in the late 60’s, having driven cross country (twice!) to get there!
He’s told me very cultivated snippets of stories here and there as I was growing up: Who he went with, what they visited, where he worked for the brief period he lived out here. All that did was give me a tantalizing glimpse of what I knew had to only be a very small portion of his story. Living in the Bay Area now, I can only imagine what it was like here then.
GRANDPOP: The west was wild and wide open in 1966. I’ll never forget the first time we drove across Golden Gate Bridge. The enormity of the orange stanchions that anchor the bridge. The gorgeous blue water of the Bay. I even paused to remember that my own father (TBR’s grandfather) wanted more than anything in the world to go to Sausalito… to this day, I’m still not sure exactly why… but it’s clear that the love for the Bay Area runs deep in our family!
Grandpop cont’d: We traveled to 27 states and 12 national parks (about half the national parks in the country at the time). We saw two dozen species of wild animals I didn’t even know existed. We spent time on eight university campuses, including Tuskegee University – a powerful and poignant place to visit during the Civil Rights Movement. The country was changing so intensely, in so many ways, that it was incredibly fitting to experience it during our own life-altering post-graduation moments!
We slept in a tent for 25 nights, stayed with relatives for another 14, slept in our car for two, and just six nights in a motel! It’s hard to fathom given the cultural freedoms of the time, but we didn’t drink, we didn’t smoke cigarettes, and the real kicker: we didn’t even know marijuana existed. (what do you think, friends? Should we believe Grandpop?)
Take Back Roads: Unlike the curated version he’s sharing here publicly, Grandpop opened up far more fully during his visit here this summer. It was incredibly refreshing and remarkably enjoyable to experience. Hearing him share deeply personal stories and the emotions they inspired will be a memory I carry with me for the rest of my life.
I can say this:Â his road trips clearly left indelible marks on him, even after almost 60 years.
There’s another story from his recent visit that ties in well here.
We were in San Francisco for the day, and what a glorious day that was. Imagine the most wonderful weather you’ve ever experienced. A breezy summer afternoon, with little humidity, abundant sunshine and a few puffy white clouds against a royal blue sky.
Now envision an exuberant floral bounty, dazzling with life: not a tropical scene, but almost as if the plants in a Dr Seuss story came to life. Audacious colors in dizzying shapes and sizes framed San Francisco’s instantly recognizable architecture, all of it set against the backsplash of the rugged Pacific Coastline and distant Golden Gate Bridge.
Yet what is most intensely seared into my memory was the moment we had while driving up one of San Francisco’s notoriously steep and twisted hills. We were talking about the differences in daily life between California vs Pennsylvania. He interjected with a pronouncement about how proud he was that I had a courage he never possessed. He’d had the opportunity to move to California during his trip, but he couldn’t find the courage to actually take the leap.
Looking back over my life, I see how much my parents – my father in particular – encouraged me to travel at every opportunity. They equipped me with the knowledge I needed to travel far afield. They fostered an open mind to absorb new experiences and the self-confidence to explore different cultures. Most importantly, they gave me the freedom to leave: I could chase after every whim and pipe dream I could imagine.
And now, I’ve passed that feeling – that confidence and freedom – on to my own kid.  I’ve always said that my greatest goal as a parent is to help my child become a fiercely independent adult. Travel – and road trips in particular – are a foundational piece of that puzzle.
Celebrating Graduation with a Cross Country Road Trip
Take Back Roads: Thus, it makes sense that an endeavor like a cross country road trip would be a great way to celebrate a monumental time of transition in life like graduation. Road trips in their very nature are built around leaving and exploring, just like graduation. Road trips are almost always well-planned (or at least, well-envisioned) adventures that are the very pinnacle of learning and growth. They provide a great capstone for the educational journey, taking the mind and body on one of its most extensive explorations of the human experience.
GRANDPOP: My road trip was planned for 48 days. It ended up being 47 … but who’s counting! I did a lot of the planning. My father helped, especially editing my early approach to our plan, offering some excellent suggestions based on his own worldly experiences. Eddie and I followed the resultant itinerary fairly closely… Although we did venture off the beaten path from time to time.
TBR: There are so many stories I could write about from my own celebratory road trip in 1999. My best friend from Austria – Dietmar – flew over to the United States after his own high school graduation (we were in the same grade). He went through the process to get an American driver’s license. Under the tutelage of my defensive-driving mother, he drove us on short exploratory trips to gain firsthand experience driving in America… which was just as hair-raising as you might expect!
Incredibly, they still let us take their car for our five week, 9,000+ mile circuitous road trip around America.
Grandpop:Â Â Edward’s father gave us the use of his old Cutlass for our seven weeks on the road. I felt like I was just paying it forward when I did that for Scott and Dietmar!
Kiddo:  And then my dad and I took his Ford truck on our first cross country adventure, after my high school graduation! The generational tradition of taking family vehicles continues!
TBR: As you can imagine, we two recently graduated hellions on a road trip – with no parents in sight! – found our fair share of mischief. Not as bad as you might imagine, but not as innocent as my parents imagination, either!
GRANDPOP: My trip after high school was comparably bland. Edward and I only had one argument, and caused basically no mischief! Anyway, I wanted to visit the Astrodome in Houston. It was new, and I’ve always been a baseball fanatic. Edward wanted to push on to get toward our next campground, so we argued. I sat on the curb outside the Astrodome, unsure of what to do. I thought about quitting.  I called my father and he gave me simple but great advice: Stay on this trip. It will be the trip of a lifetime. Boy, was he right!
TBR: Now, as the creator and host of Take Back Roads, it pains me to admit this: the majority of our road trip was taken on the interstate. Yes, there were stretches of the trip that were on the back roads, but back then, the driving was something to get through. For most of our trip in 1999, we took the highway. I can only imagine the scenery we missed!
Kiddo:  Our trips were a blend of both. For the long flat stretches across the middle of the country, we took mostly interstate to save time. Once we got to the beautiful mountains in Colorado and Wyoming, we only drove on back roads!
TBR: I’ve tried to think of driving experiences from my 1999 road trip that stand out in my memory. Aside from the sheer misery of boredom that is driving across west Texas, there isn’t a single driving-related back road experience that I can recall.
But there was a singular paradigm-shifting moment in the early stages of our trip that changed our mindset for that adventure, and for every travel experience I’ve had since then.
Exploratory Detours and Side Quests
Take Back Roads: I would love to have a charming story about a captivating experience we had while tackling an amazing road trip side quest. We didn’t – our first detour was enjoyable enough, though it turned out to be not all that interesting. We kicked up a lot of dust on the sun-dried farm roads, fed some beautiful horses and saw lots of lush pastures.
But what we found was the real gem: a change in perspective – both on road trips and in life. The real key to success isn’t executing a properly mapped-out plan; it’s the ability to be flexible and free when the situation calls for it.
We were slogging our way across the unending Midwestern cornfields when something off in the distance caught our attention. No clue what it was now – time and age have deleted that file from the hard drive. But it captured us, and we quickly decided in that moment that our destination could wait.
We were going on a side quest.
As I already mentioned, the end result of that first detour wasn’t altogether memorable. But we both loved it. The freedom we felt – the freedom to ignore the plan and follow our hearts – when we experienced that feeling fully for the first time in either of our lives… it changed us both forever.
You might even say that the rest of my life has been a never-ending string of side quests and impromptu adventures. Hell, even the reason I moved cross country was because of a side-quest-turned-camping-adventure on our way to Joshua Tree in 2017!
I’m not going to bore you with stories about all the things we did on our trip in 1999. We did stupid teenage boy shit. While playfighting at 75mph somewhere in Kansas, Dietmar bumped the shifter into reverse and we thought our trip was over before it had even started. We saw crazy shit, too – heading down 101 to Santa Cruz, we saw two cars collide in front of us then slam into the bridge supports on either side while we passed through unharmed in the middle.
We flirted with girls and walked through drive-throughs and tried to get into bars (failed pro tip – “places by military bases don’t card as much” turned out to be a lie). We stayed in hostels and stayed with friends and even stayed in a hotel on the Strip in Las Vegas (our lone splurge of the entire trip). We ate cases of Ramen we carted in the trunk and had more canned tuna than I care to recount.
In talking with Grandpop and Kiddo about our cross country road trips, a unifying theme runs throughout: More than anything, we learned how to be the captains of our ship. The leaders of our lives. To be independent. To navigate the world around us. We learned how to learn just by being open to all the myriad things life has to show us. We learned how to say yes to adventure, say yes to experience, and say yes to exploration.
Just say yes, friends. That’s the real moral of this story. You never know where the road may take you when you just say yes.
I so enjoyed your story. I didn’t know many of these things about Grandpop!
What a wonderful read! You need to publish a book!