6 days on Route 66 provides 2319 miles of mostly old-fashioned fun

As I struggled to lift the iron cylinder head off the Chevelle’s big-block V-8, the last thing on my mind was driving this old Chevy across the country. But I had to admit, my kid had a great idea. “We should drive it on Route 66,” he said, “for spring break.”

Sam, my younger son, is nine. The longest car trip he’s taken is a 10-hour ride to Grandma’s in New Jersey when he got to watch his favorite movies on an endless loop. He doesn’t yet know how fun-filled, multi-day car trips so often descend into misery—with extreme boredom and petty spats—that Hollywood famously parodied the activity in 1983’s National Lampoon’s Vacation. Sam doesn’t realize that his teenage siblings and mother probably don’t want to spend our only annual family sojourn jammed inside a four-wheeled metal can.

The pieces started falling into place when the female contingent of our five-person family fell out. That left Sam, me, and 15-year-old John, who was just old enough to act as relief driver.

The holdout was me, the guy who does at least a handful of solo road trips every year. When I was a kid in the 1980s, my family of five drove up and down the East Coast in a 1979 Chevy Suburban since we couldn’t afford to fly. Sure, there were some bright spots, but the stories we now tell from those excursions are more often about my parent’s epic fights or the time the Suburban vapor-locked on Interstate 95. We now laugh at the pain, but are those the memories I want to create with my sons?

Obviously, no, but here was my chance to include my boys in something I love to do and show them the country outside Ann Arbor, Michigan, perhaps applying lessons from my childhood trips. Plus, this journey was a damn good reason to get our old Chevy back together. Let’s roll.

Near the beginning of an eastward journey on Route 66, the author’s sons take in Arizona’s majestic Humphreys Peak.
Near the beginning of an eastward journey on Route 66, the author’s sons take in Arizona’s majestic Humphreys Peak. James Lipman

Since we had only a week’s vacation, driving Route 66 to the West Coast and back was out of the question. Instead, we decided to ship the car to Phoenix, visit the Grand Canyon, and then drive home on as much of the road called “America’s Main Street” as we could handle. Spring break 2018 was the last week of March, eight weeks away, and the Chevelle’s motor was in pieces. A mad rush ensued.

The three of us had taken the engine apart to hop it up with a new camshaft, aluminum heads, headers, and other bits hoping to knock at least a second off the car’s 15.02-second quarter-mile time. Again, an idea from Sam that John and I were eager to indulge. We thought we had the entire winter to finish the job, but then the Route 66 idea popped up. My lack of engine expertise was, to say the least, slowing things down.

So it was a great relief when, a few weeks before departure, the 427 thundered to life, the exhaust bellowing out of the open headers and rattling the neighbor’s windows. The boys and I woofed and hollered like we’d just won the Super Bowl. The untested Chevelle soon rumbled into a trailer and headed west to Phoenix. A shop called Vintage Iron had agreed to fabricate a new exhaust system and store the car until we arrived.

Then my 77-year-old mother called and said she wanted in. Oh, boy. In her youth, Mom was as tough as they come, but 10 years ago, she came terrifyingly close to losing a cancer battle. Furthermore, my Brooklyn-born mom is no wallflower, and we are prone to lock horns. I wanted her to lay eyes on the Grand Canyon for the first time, but I worried about her health, and selfishly, I thought her attendance could add tension. But she’s my mom; how could I say no? I brokered a deal: Meet us at the canyon and hang until Albuquerque.

Finally, on Friday afternoon, March 23, we made it to Vintage Iron. The guys there had rectified several potential trouble spots, but now that the Chevy had an exhaust, they discovered—just before we arrived—a loud ticking noise in the engine. What, I wondered, had I screwed up? As my sons and I stood at the front of the car listening to the tick-tick-tick-tick, the mechanic asked, “What do you want to do?”

I wanted to scream. Hanging around to investigate the noise meant ditching the hard-to-get hotel reservations at the Grand Canyon and opening the proverbial can of worms. That was probably the prudent move. But the noise sounded to me like a loose valve lifter, a diagnosis I confirmed with the mechanic. This loose lifter could, I reasoned, harmlessly tick all the way to Michigan. Or there could be a more sinister problem that could blow the engine. I thought that was highly unlikely, and even if it did happen, I have Hagerty roadside assistance, and we’d have a story to tell. We piled in and left.

Chevelle wagon back seat john checks his shots
John checks his shots James Lipman
Nine-year-old Sam Webster, left, came up with the idea for the Route 66 family road trip and is evidence that kids still love cars.
Nine-year-old Sam Webster, left, came up with the idea for the Route 66 family road trip and is evidence that kids still love cars. James Lipman

There is almost no traffic on Route 66. chevelle wagon
There is almost no traffic on Route 66. James Lipman

“Is the ticking louder?” I asked John. Four days after Phoenix, we were running 80 mph on a congested, dark, and rainy highway outside Tulsa, Oklahoma. I was fairly sure the engine was about to blow.

This long stretch of highway was under construction, the two lanes lined with concrete barriers, no shoulders. The lack of an escape route, fatigue, and the stress of keeping up with traffic sent my mind to dark places. What if the engine quit and I had to coast to a stop in the middle of traffic? Would the other cars see our relatively low and dim taillights? Why hadn’t I recognized that our modified car—it has a five-speed manual, not the original automatic—didn’t have flashers? How could I have been so reckless?

Finally, salvation: The hotel, booked a few hours earlier for the sole reason that it had an indoor pool, came into view. I splashed in with the kids just a few minutes before it closed at 10, washing away the day’s stress and reminding myself to avoid the have-to-get-theres.

So far, a keep-it-loose strategy had worked perfectly. After standing on the edge of the Grand Canyon, watching Mom nearly tear up at the grandeur, we had meandered our way eastward using a couple of guidebooks and stopping at places we’d heard about.

Sam wanted to stop at Mary’s Café outside Flagstaff because it was featured in an episode of Roadkill (the Roadkillers went there because the café was a seminal stop in the 1971 movie Two-Lane Blacktop). Sure. While kicking a soccer ball around a park, we met a woman walking her dog who told us not to miss Walnut Canyon National Monument and its mile-long trail among the cliff dwellings. She was right; it is spectacular.

We walked inside carefully crafted stone rooms that were built under natural limestone ledges. The original tribe stayed for hundreds of years and then, for reasons not completely clear, simply left the village behind. Route 66 is filled with similar ghost towns and villages that are empty except for a few holdouts. The decaying motels and unlit neon signs might be viewed as depressing artifacts of an era left behind. Walnut Canyon was a reminder that humans are migratory creatures and nothing is forever.

Chevelle on road drone above shot
James Lipman

We arrived in Holbrook, Arizona, with hours of sunlight to spare and checked into the Wigwam Motel, a landmark on Route 66 because the rooms are a cluster of simulated tepees. Every 20 minutes or so a freight train rumbles by behind the complex, so we made souvenirs by putting coins on the tracks and explored the nearby freight yard. John, the teenager, had barely touched his phone since we left the airport, a small triumph in my book.

The following day, our third, we hopscotched to the Albuquerque airport, said goodbye to Mom, and then considered our options over milkshakes at the Route 66 Diner. I hoped to visit the Unser car museum or at least take a tram ride up nearby Sandia Peak, but I was roundly outvoted. Sam was hot for Amarillo, and John simply wanted to keep moving.

That was a challenge. Much of Route 66 is bypassed, unmarked, or slowly deteriorating back into the earth. Staying on it demands constant vigilance as it frequently crosses I-40 and most guidebooks are geared toward westward travel. There’s also the frustration of rolling at 45 mph parallel to the interstate where we could be going nearly double the speed.

Little did we know we had a four-foot Zen master with us. Sam, our purist, kept us on the Mother Road, reminding us to stick our elbows out the open windows, watch the desert roll by, and let the wind rustle our hair. That kid is a true advocate for living in the moment, and John and I followed his lead. We sang the songs on our communal playlist, which we piped through the car’s stereo, secure in the knowledge that no one else could see or hear us.

I’d pull over from time to time and offer John the wheel. In the beginning, he gladly took it, but he couldn’t come to grips with the Chevelle’s antiquated steering. Consequently, his lane changes were jerky. On one unavoidable highway stretch, I looked up from my book and realized John was going 80 mph while passing an equally fast semitrailer on the outside of a downhill curve. He kept oversteering, turning the wheel too much and then overcorrecting. Suddenly, we were in trouble, weaving back and forth at speed and in traffic.

None of us breathed the next few seconds as the road straightened out and John got his bearings. I never said a word, not wanting to add to the pressure I saw on his face. John took the next exit and got out of the car. “I don’t want to risk it,” he said when I later tried to get him back on the proverbial horse, showing a far greater sense of responsibility then I had at his age. Later, I figured out the problem: There’s a beat or two delay between the time you turn the Chevy’s steering wheel and when the car responds. I learned to drive on similar Chevys, but John trained on video games and his mom’s minivan. So when he turned the Chevelle’s wheel and nothing happened, he simply turned more.

Established in 1926, Route 66 originally ran from Chicago to Los Angeles. It carried many families to jobs in California during the Great Depression.
Established in 1926, Route 66 originally ran from Chicago to Los Angeles. It carried many families to jobs in California during the Great Depression. James Lipman

I should have given him better instruction, or at least told him to lift off the gas on that curve. My laissez-faire parenting has its downsides. For a second I wondered if we should have rented a newer car, which probably would have been cheaper. But the Chevelle kept us from being invisible travelers and introduced us to people we would not have otherwise met. In Tucumcari, New Mexico, a bearded city worker stopped to ask about the car and then solved the mystery of a creepy abandoned building we had just spelunked. It was, he told us, a creamery with a once hopping ice-cream stand. Gas stops turned into mini–cars-and-coffee gatherings. Finding a key for the Chevy would later give us one of our favorite memories, but first, there was Texas.

The Route 66 motels in Amarillo looked sketchy, so we broke our roadside-motel rule and slept in a high-rise in the sparse downtown. The next morning, while debating what to do that day, I called the operator using the room speakerphone:

“Hi, does the hotel have a pool?” I asked.
“No,” the deadpan female voice replied.
“Are there any public pools nearby?”
“Well, we’re just passing through. Anything we should see while we’re here?”
“Hmm, not really.”
“So,” I said, “we should just pack up and get the hell outta here?”
“Pretty much.”

The boys fell to the floor in laughter.

We ignored that advice and stopped at Cadillac Ranch before leaving Amarillo. The 10 old Caddys stuck halfway into the ground were, to me, anticlimactic, but Sam found great joy spray-painting the stripped bodies, a perk recommended by an Amarillo waitress who wore eye makeup in layers, like Tammy Faye Bakker’s. This kind woman gave us latex gloves as we left her diner, a welcomed gesture after our hotelier told us to scram.

The road trippers in Mary’s Café, an Arizona restaurant featured in the 1971 film Two Lane Blacktop. It’s one of the few little-changed diners along Route 66.
The road trippers in Mary’s Café, an Arizona restaurant featured in the 1971 film Two Lane Blacktop. It’s one of the few little-changed diners along Route 66. James Lipman

The morning of our fourth day on the road was overcast and chilly, the first time we wore our coats. Route 66 to the east was getting more interesting because it was farther from I-40, and the concrete surface and molded curbs looked original. Sam read in the back seat as the miles rolled under us. By midday, I noticed John sneaking more peeks at his phone.

Although there are parts about smartphones I love, I sometimes wish we could put that genie back in the bottle, especially when I’m with my kids. It’s hard to compete with a device that chirps at a teenager constantly to urge him to chat with his friends. We did, however, have a gentleman’s agreement that went something like this: Take some time in the afternoon to catch up, but don’t let the phone be the boss. That seemed to work for a while, but now that I was doing all the driving, John was bored. And frankly, the slow pace on Route 66 lulled me, too.

In Erick, Oklahoma (pop. 1052), 150 miles west of Oklahoma City, a freshly painted sign advertised an airport. I reflexively followed it because it seemed so out of placein the tiny forlorn town. Maybe there was something that could reenergize us, like a plane ride. Instead, we found a desolate and thin asphalt strip surrounded by cotton fields and a couple of tired hangars. We parked on the runway and got out a football and ran around like madmen for an hour, trying not to trip in the gopher holes.

This recreation lightened the mood, and we sat on the hood to debate our options. John revealed his boredom and wanted to go home. Sam announced he’d stay on the road for another month, easy. As the drizzle slowly chased away the body heat we’d just generated—with more rain to come—I admitted that I was closer to John’s camp. With my kids, I’ve learned the leave-them-wanting-more strategy rarely fails, so I suggested a night in Tulsa, then St. Louis, and then home. We all agreed and then I remembered a tip I once read to keep kids entertained during long car trips: a Harry Potter audiobook. I immediately downloaded one to my phone, which kept us all entertained as we headed east to Tulsa and our date with that scary section of interstate.

Once free of Tulsa, we followed Route 66 for one last stretch to Baxter Springs, Kansas, where Jesse James supposedly robbed a bank. We’d been meaning to get a spare key from the start but kept forgetting. A 60-year-old woman at the local hardware store cut the new key while her twin sister stocked shelves nearby. After 10 minutes and $2.73, she handed over the key and told us in a warm Midwestern accent to bring our “vee-hick-cle” by so she could check it out. I can’t tell you why, but we all smiled at this pronunciation and tried to mimic the accent for the rest of the trip. And still do today. (The key worked.)

A cheap mechanical oil-pressure gauge was hastily installed before departure.
A cheap mechanical oil-pressure gauge was hastily installed before departure. James Lipman
Freight trains were a constant companion along Route 66, which was home to hundreds of “diners,” built in the shape of railroad cars. Some of those originals still exist.
Freight trains were a constant companion along Route 66, which was home to hundreds of “diners,” built in the shape of railroad cars. Some of those originals still exist. James Lipman

Blue chevelle from above drone doors open
James Lipman

A massive rainstorm scuttled our plans to ascend the St. Louis Arch. Instead, we made one last stop at an indoor go-kart track in Indianapolis and then let Mr. Potter take us home, six days and 2319 miles since we started.

There’s a lot of parental pressure to make family vacations like nonstop Walt Disney World amaze-fests. Disney would have been easier and probably cheaper, but I saw a greater opportunity in our journey. I wanted my kids to feel the satisfaction of self-determination: We had a dream and put in the sweat equity to make it happen. Success or failure was up to us. For me, this trip was a smashing success as soon as we drove away from Phoenix. We already had a vibrant and uncommon experience together, bonding by way of a big-block Chevy. I hope some portion of their brains, wedged between video games and sports, felt something similar. But who knows?

In the years ahead, what are the memories that will stick with them? Will it be the evening we rolled along the Arizona desert with the sun setting behind us, singing Black Sabbath’s Iron Man? Will it be the Amarillo hardware store where we bought header bolts to replace the two that mysteriously backed out? Did they appreciate how terrific it was that we found fun in a desolate airfield and never got on each other’s nerves? Or will they look back and think of the rough last few hours before we got home, driving in the constant rain and wishing for our beds? Perhaps their memories don’t matter so much because I know our imperfect trip taught them far more than Disney ever could. I was curious to know how they felt about the journey, especially John, but I was afraid to ask. The boys would dutifully respond positively, not wanting to disappoint their old man who they knew went through a lot to make the trip happen.

As the days went by, though, I got some clues. I overheard John, who is on the reticent side, talking to his cousin on the phone, telling stories from the road and laughing. Sam asked me to help him make a slideshow for his class. The three of us continue to retell the inside jokes that only long hours in a car make funny. And then, a week after we returned, I tucked Sam in and noticed three flattened coins on his bedside table. He smiled and said, “They’re from Arizona.”

The article first appeared in Hagerty Drivers Club magazine. Click here to subscribe to our magazine and join the club. 

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    What gearhead would not love this splendid story. The Webster family is my kind of family. I am sure future adventures await them.

    Loved it!!! Route 66 is gradually disappearing – we’ve used it for parts of a trip from SoCal to Albuquerque. Just like an old country road but some group has painted “Route 66” on the asphalt at a few spots.

    What a wonderful story, I hung on every word!! You men had a trip of a lifetime! I too am a family man with 2 boys. I redid a 70 vw beetle( baja’d) with them both, Mathew(older) was my mechanic helper, and Nicholas( car owner and paint and body younger sibling) and we would take “Herbie” on many adventures. I hope they take those memories with them forever as I do. There isn’t much we wouldn’t do for our boys and bonding moments , so thanks for sharing your story and if your ever in Washington state look me up!

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