American road trip: Three generations, two cars, 2,000 miles on Route 66

It was a once-in-a-lifetime opportunity to drive Route 66 from Chicago to Santa Monica, California, with my kids and my parents as part of USA TODAY's American Journeys series.

I was nervous about taking young kids on such a long trip, but everyone agreed that an article about the great American family road trip taken on the Mother Road's 100th anniversary had to include my family.

Then my father lost both of his siblings in eight months. The chance to deepen my relationship with my parents and theirs with their grandsons as we drove two-thirds of the country held new meaning.

I tried to prepare Robbie, 6, and Tommy, 4, by watching "Cars" and talking about how Radiator Springs got left behind when the highway moved.

Planning began a year out. Balancing the interests, needs and attention spans of three generations took coordination. We'd each driven parts of the route, but always as a means to an end, not something to savor. 

My husband, John, and I used to brag about measuring time in miles. One Christmas, when the kids were sick, we drove 17 hours straight from Washington, DC, to Kansas. Route 66 demands a different mindset.

Built in 1926 as “the shortest, best and most scenic route from Chicago through St. Louis to Los Angeles," according to the Route 66 Highway Association, the road is now about the trip, not the destination.

Route 66 was a path to new opportunity during the Great Depression and the Dust Bowl. John Steinbeck called it "Mother Road" in his 1939 novel, “The Grapes of Wrath." The Route's image as a place of freedom and "kicks" solidified after World War II, as American tourists had the money to explore their country. Meanwhile, President Dwight Eisenhower began pushing for the creation of high-speed interstates, a move that led to the Route's official demise.

Even though the federal government officially removed the road from the federal system in 1985, Americans moved to preserve and expand it. Hundreds of thousands now travel Route 66 each year, including foreign travelers, honeymooners, retirees in RVs and families trying to connect. COVID-19 made Route 66 more attractive for domestic travelers, Rhys Martin, manager of the National Trust for Historic Preservation’s Preserve Route 66 program, told me. So did Disney/Pixar’s Cars in 2006.

"Be careful. It will get into your blood,” he warned.

I was just hoping to build memories.

The six of us had never been together this long. My career pulled my husband and me thousands of miles from both sets of our parents. We fit in a few days or even a week a few times a year, just long enough to reconnect before separating again. 

At two weeks out, my excitement competed with my anxiety. At night, I'd stare into the darkness; was it smart to put all of us through this trip?

Chicago and the Land of Giants

Chicago-style pizza and a photo of our reflections in the bean sculpture "Cloud Gate" were necessary before we snagged a photo at Route 66’s most recent starting point.

Tommy would have lain on his belly all day and watched the arapaima ‒ a massive freshwater fish that can breathe air ‒ in the Shedd Aquarium's Amazon exhibit. Robbie befriended the beluga whales, naming one “Friendly.” 

Robbie was already asking how long until we flew home because he wanted to tell his friends about the Bowmouth Guitarfish we saw. It took a few more days before either boy grasped just how long the drive would be.

Early on, John and I pulled a trick from our own childhoods, asking Robbie to count cars on a passing train.

After stopping at the Gemini Giant in Wilmington, Illinois ‒ one of dozens of the more than 18-feet-tall roadside attractions along the route ‒ we fell into a rhythm of hopping in and out of the car: more giants, preserved gas stations, a Route 66 Museum. We made it to Lincoln’s Tomb in Springfield, Illinois, five minutes before the cemetery gates closed and we nearly got locked inside.

We tried to put Robbie with the grandparents after lunch, but he didn’t want to be away from his brother.

The old road runs right along the modern replacement, grass and weeds gradually breaking it up. We pulled over to stand on it for a few minutes. The wind howled in our ears as we tried to picture the lives that passed over it.

Missouri curves

Walking across the old Chain of Rocks Bridge gave everyone a chance to stretch their legs. It also gave us our first taste of the wind that would follow us across the state. 

The boys started to settle into the reality of a road trip: reading, playing with stuffed animals and staring out the window. We introduced our favorite road trip game, yelling “cows” or “horses.”

As Route 66 followed hills and bluffs, we passed towns my Missouri-native husband didn’t know existed. The boys filled a bag with taffy from US 66 Outpost in Fanning, home to the world’s second-largest rocking chair.

At a diner in St. James, the boys split a strawberry milkshake. They fought over who got to sit next to Papa Bob. Both did.

From the next table, Debra Holbrook, 70, asked us for directions. Five days after learning Route 66 was on her husband’s bucket list, they left New Hampshire with their rescue dog, Blaze. 

“My garden can’t go in till after Mother’s Day, so I figured, 'Hey, there’s this six-week window,'" she said. “I said, 'Let’s just do it.'”

Past bedtime, we raced to the hotel in Springfield and got our first glimpse of the Route’s legendary neon signs. Tommy plaintively asked, "Why are you driving everywhere?" 

Roadside kitsch

Pixar animators studying Route 66 for "Cars" based Tow Mater on a rusty truck with a tree growing out of it in Galena, which sits on Kansas' 13 miles of Route 66, said Renee Charles, owner of the Cars on the Route tourist attraction.

Down the street, Gearhead Curios owner Aaron Perry said he dreamed of owning a piece of Route 66 after driving it to visit family as a child. The old Texaco gas station he bought in 2018 had no roof. Trees grew through its bathroom.

“I tell people Route 66 is the dreams, the what ifs, the what was, the what could be,” he said.

At the Crosstar Flag and Tag attraction in Afton, Oklahoma, the owner allowed the boys to climb inside some of the cars. For the rest of the trip, Tommy tried to open every old car he saw. 

Small town charms

We decided that if the boys wouldn’t switch cars, the adults would. Nana rode in the minivan with me as we left Tulsa. We got eyerolls when we sang "She'll Be Comin' Round the Mountain." It had been a long time since we sang together. 

The kids finally asked to watch TV in the car. I conveniently forgot to mention the tablet as we passed a giant thumbtack and matchstick in Wellston, Oklahoma. In Arcadia, we stopped at the oldest attraction on the Route. Built in 1898 and painted red, the Round Barn smelled of bur oak wood and dried grass.

Robbie said he wished we hadn't gone on the trip. My heart sank. Five minutes later, he happily skipped his way into Pops 66 Soda Ranch for his first soda.

The road to see the longest bridge on the Route, the 1933 Pony Bridge near Bridgeport, was cracked and bumpy. Suddenly, the scenery changed from flat and brown to green and purple scrub brush-covered red dirt hills. The span was closed, so we got to watch the transition in reverse.

Family on the road

Three museums in a day was ambitious. Papa Bob hopped into a training cockpit at the Stafford Air and Space Museum in Weatherford. At the Oklahoma Route 66 Museum in Clinton, the boys read, touched and heard the story of the road, decade by decade.

The woman at the front desk of the Devil’s Rope Museum in McLean, Texas, was thrilled Bob Wire was visiting the barbed wire exhibits. She even checked his driver’s license.

We ended the day in Amarillo, which holds a piece of my heart. My granny lived there with my dad’s sister, Susie, and her husband, John, for the last decade of her life. I had put off telling Susie we might visit because I didn’t want to get her hopes up. John and Susie met Robbie at his first Christmas but had never seen Tommy. Susie died two months before my trip was approved.

Uncle John showed the boys his horse, Levi, and taught them how to feed him. It felt unfair that Susie wasn’t standing beside him and waving goodbye as we left.

Cadillac Ranch as the sun rose

The clouds over Cadillac Ranch at sunrise will stay with me forever. Robbie, Papa Bob, John and I walked along the dirt path and applied our names and the year in a layer of light blue spray paint, permanently adding our journey to the art installation.

I begrudgingly shared bites of my cherry cobbler at the Midpoint Cafe and Gift Shop in Adrian, Texas. Owner Brenda Hammit Bradley told me she plans to sell at the end of the year, “I love this place, but I'm 65 years old and I'm tired. I make a lot of pie and if I never saw another pie pan again, I would be a happy lady."

Much of New Mexico’s Route 66 is under the interstate or on dirt roads, which we would have taken if I trusted the rental minivan to survive.

Tucumcari’s murals, neon signs and the Blue Swallow Motel were delightful. The scent of sagebrush wafted over it all. The fossils and bronze skeletons in the Mesalands Community College's Dinosaur Museum kept the boys entertained.

We had ice cream twice

The dozens of creatures at Albuquerque’s Rattlesnake Museum lived up to Robbie's expectations, especially when one rattled its tail.

We passed Owl Rock and Dead Man’s Curve on Laguna Pueblo land. It was heartbreaking to see the mesa that was blasted through to build the four-lane Route 66, which eventually became Interstate 40. Dramatic pink mesas popular in cowboy movies dominated the skyline as far as we could see.

We stopped for an afternoon ice cream at Dairy Queen, a childhood tradition my dad continued with his three other grandsons, but hadn't yet done with my boys.

In Gallup, dinner came with free scoops of ice cream. We almost said no. But who knows, the day the kids got ice cream twice might be their favorite memory from the trip.

Hiking with Papa Bob

Robbie declared Petrified Forest National Park's Painted Desert "a-maz-ing." John almost drove off the road at the sight of the blue mesa.

I tried not to get misty-eyed as the boys chattered at Papa Bob while hiking the Crystal Forest, another first.

We did the touristy thing and stood on the corner in Winslow, Arizona, and then scrambled to find a restaurant open on Easter while humming the Eagles' “Take It Easy.” At the La Posada Hotel restaurant, the boys embraced Nana's favorite grandkid game of "don’t wipe off my kisses." Every meal ends with a pile of crayon drawings for her refrigerator.

Grand Canyon

The Grand Canyon is breathtaking and also terrifying with a 4-year-old along.

Taking it in for the first time, Tommy asked, "Is this the giant 'normous Canyon?" For the next few hours, he reassured me he would not jump in. Then he walked toward the edge.

Finally, my heart couldn’t take it. We took the shuttle back and drove the park ourselves. My newfound fear of heights quickly disappeared when Tommy napped.

Even in my mind's eye, the view still takes my breath away.

"It really gets to you," my dad said.

He last visited at age 18, thinking he could hike down and camp until a ranger asked for his permit.

Multiple people have told me about falling in love with Route 66 and driving it over and over. For me, it opened something wider. I want to explore what else I’ve missed. I hope this trip creates that restless feeling for my boys, too. What's over the next hill? What stories are waiting? I hope they take me along.

The sidewinder

In Seligman, Arizona, you can see Route 66's legacy of dirt, brick and asphalt under the existing road. This is where Angel Delgadillo fought to save his hometown after I-40 bypassed it. He helped protect the highway nationwide. Seated in her father’s barber chair, Mirna Delgadillo, 62, said preserving Route 66 protects our history.

“Do we know where we’re going, if we don’t know where we came from?” she said.

The “sidewinder” is the kind of road you hope exists somewhere. It climbs 3,550 feet through the Black Mountains, twisting through blind hairpin turns.

In Oatman, an old gold mining town, donkeys followed tourists along the boardwalks and into stores. Just like the boys, Nana was as giddy to feed the donkeys grass pellets that sold for a dollar a bag. Tommy named them. Robbie found his souvenir for the day, a rattlesnake stuffie in a can. Thankfully, Papa Bob had a can opener, sparing us hours of hearing about it.

I joked over the walkie-talkie about camping beneath a jagged roadside monolith.

“You are your father’s daughter,” my mom replied. “He just said the same thing.”

California desert

When Nana played her kisses game at breakfast, Robbie made sure she knew he didn’t wipe them. Tommy laughed, doing the opposite.

On the lonely stretch of road along the Mojave Desert, I was struck by how much of the country ‒ cities, ghost towns, small towns, mountains and prairies ‒ we had crossed in just two weeks.

Past Roy's Motel and Cafe in Amboy, the kids started to argue. So we rolled down the window and they both stuck a little hand out to ride the wind. The boys ran around the teepees at the Wigwam Motel in San Bernardino. We hopped into the pool with Papa Bob, another first.

Dipping our toes in the Pacific

In the Los Angeles area, the game of shouting out when we saw a cow or horse became shouting out whenever the boys saw a palm tree.

We grabbed pre-lunch ice cream at the Fair Oaks Pharmacy in South Pasadena and the boys played with whoopee cushions and Slinkys from my childhood. Nana bought shark and snake hand puppets as gifts for them.

The line at the Santa Monica Pier ending point moved quickly. We were all impatient to walk out to the waves. 66 to Cali operator Ian Bowen filled out our certificates of completion.

Dipping our toes in the Pacific Ocean turned into an hour of the boys playing in the waves fully dressed.

Tears goodbye

To mark the end of our trip, Nana and Papa Bob splurged on a whale spotting tour, the same one they took with two other grandsons 15 years earlier.

Nana and the boys were leaning against the railing as a fin whale exhaled. Robbie yelled: "There, it's there!" Tommy and I peeked through the railing as it came up again.

Robbie spoke with the naturalist, who pulled bottles of krill and whale poop from his pockets. Then my want-to-be oceanographer declared himself a whale expert. Tommy cozied up between Nana and Papa Bob, munching from a tub of popcorn.

As our journey across Route 66 came to an end, I began to understand the emotional pull it has had on so many Americans.

You never want your kids to cry. You do want them to love. Robbie and Tommy hugged Nana and Papa Bob goodbye. As we walked away, Robbie ran back to them in tears for another hug.

I didn't know until that moment that a hug was what I was hoping for from the trip.

I was always the emotional kid who sobbed when we left my granny and Aunt Susie behind in Amarillo. My dad would say it was proof I loved them. I told Robbie the same.