Route 66 family trip turns 2 weeks into forever

On Route 66’s 100th anniversary, a two-week drive from Chicago to Santa Monica with three generations became less about distance and more about time—especially after a family loss reshaped what “together” meant.

When the car finally crossed into Los Angeles County and the kids started shouting about palm trees. the road trip stopped feeling like a map. For two weeks straight. Route 66 became a moving promise: that everyone would make it to the next stop. the next hug. the next view—no matter how unpredictable time could be.

The stakes were emotional before the first mile. It was Route 66’s 100th anniversary, and the plan was a once-in-a-lifetime drive from Chicago to Santa Monica, California, with kids, parents, and space enough to remember why they were all in the same vehicle at the same time.

Planning began a year out. Coordinating the interests, needs and attention spans of three generations took work, and it came with nerves. The writer tried to prepare 6-year-old Robbie and 4-year-old Tommy by watching “Cars” and discussing how Radiator Springs was left behind when the highway moved. The group drove together in parts. not to savor every mile like a trophy. but as a means to an end: memories.

Then the family’s schedule was given a sharper edge. The writer’s father lost both of his siblings in eight months. The chance to deepen relationships with parents—and for their grandsons to share time—took on new meaning as the trip approached.

Route 66’s history sat quietly in the background, even as the family chased roadside sights and small-town stops. The road was built in 1926 as “the shortest, best and most scenic route from Chicago through St. Louis to Los Angeles. ” and it is now described by the Route 66 Highway Association as a route “about the trip. not the destination.” John Steinbeck called it the “Mother Road” in his 1939 novel. “The Grapes of Wrath.” The image of freedom and “kicks” solidified after World War II. when American tourists had the money to explore.

The federal government’s push for high-speed interstates—driven in part by President Dwight Eisenhower—led to Route 66’s official demise. Even though the road was removed from the federal system in 1985, Americans kept trying 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, and Disney/Pixar’s “Cars” in 2006 added to the draw.

“Be careful. It will get into your blood,” warned Rhys Martin, manager of the National Trust for Historic Preservation’s Preserve Route 66 program.

Before the trip, even the household rhythm had been shaped by long distances. The writer and her husband, John, had once bragged about measuring time in miles. One Christmas, when the kids were sick, they drove 17 hours straight from Washington, DC, to Kansas. Route 66 demanded a different mindset—slower, more intentional, ready for surprise.

Chicago to Springfield: reflections, roadside giants, and gates that almost shut

In Chicago, pizza and a photo at “Cloud Gate,” the bean sculpture, came first—before the family snagged a picture at Route 66’s most recent starting point.

Tommy would have stayed in place all day watching the arapaima. a massive freshwater fish that can breathe air. in the Shedd Aquarium’s Amazon exhibit. Robbie befriended beluga whales. naming one “Friendly.” Robbie was already asking how long until they flew home. because he wanted to tell friends about the Bowmouth Guitarfish the family saw. It took a few more days before the boys fully grasped how long the drive would be.

To ease the early miles. John and the writer used a trick from their own childhoods: asking Robbie to count cars on a passing train. At the Gemini Giant in Wilmington. Illinois—one of dozens of roadside attractions along the route over 18-feet tall—they shifted into a rhythm of getting out of the car for stops that turned the road into a chain of moments.

They visited more giants, preserved gas stations and a Route 66 Museum. In Springfield, Illinois, they reached Lincoln’s Tomb five minutes before the cemetery gates closed, nearly getting locked inside.

The road also tested patience. They tried to put Robbie with the grandparents after lunch. but he didn’t want to be away from his brother. The old road ran alongside the modern replacement. grass and weeds breaking it up as they pulled over to stand on the older pavement for a few minutes. The wind howled as they tried to imagine the lives that had passed over it.

Across Missouri: bridges, diners, and a bucket-list window

Walking across the old Chain of Rocks Bridge gave everyone a chance to stretch and offered their first taste of the wind that would follow them across Missouri.

The boys began to settle into the reality of road travel: reading, playing with stuffed animals, and staring out the window. The family introduced a favorite game—yelling “cows” or “horses”—and as Route 66 followed hills and bluffs, they passed towns the husband hadn’t known existed.

At US 66 Outpost in Fanning, the family filled a bag with taffy. In a diner in St. James, Robbie and Tommy split a strawberry milkshake and fought over who got to sit next to Papa Bob—both times, at the table’s center of gravity.

From another table, Debra Holbrook, 70, asked for directions. Five days after learning Route 66 was on her husband’s bucket list. Holbrook said they left New Hampshire with their rescue dog. Blaze. Her garden can’t go in until after Mother’s Day. so she pointed to a six-week window and decided. “Let’s just do it.”.

Neon signs came later that day, and Tommy’s question—why they were driving everywhere—captured the constant tension between travel plans and small attention spans.

Roadside kitsch in the Midwest: reflections of “what if”

In Galena, Kansas’s 13 miles of Route 66 included Pixar’s “Cars” trail. Renee Charles. owner of the Cars on the Route tourist attraction. said Pixar animators studied Route 66 for “Cars. ” based on Tow Mater on a rusty truck with a tree growing out of it. Nearby, Gearhead Curios owner Aaron Perry described how Route 66 dreams became literal when he bought a piece of it. Perry drove it as a child to visit family. then bought the old Texaco gas station in 2018—without a roof. with trees growing through its bathroom.

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

In Afton, Oklahoma, at the Crosstar Flag and Tag attraction, the owner let the boys climb inside some old cars. For the rest of the trip, Tommy tried to open every old car they saw.

Oklahoma and Texas: switching cars, museums, and a loss that never fully leaves

In Tulsa, a long stretch of small-town life meant adults and kids swapped roles to keep everyone moving. Nana rode in the minivan with the writer as they left Tulsa. Everyone rolled their eyes when songs like “She’ll Be Comin’ Round the Mountain” started up. Eventually. the kids asked to watch TV in the car. and the writer conveniently forgot to mention the tablet—especially while passing a giant thumbtack and matchstick in Wellston. Oklahoma.

In Arcadia, they stopped at the Round Barn, the oldest attraction on the Route. Built in 1898 and painted red, it smelled of bur oak wood and dried grass.

At one point, Robbie said he wished they hadn’t gone on the trip. The moment landed hard. Five minutes later, Pops 66 Soda Ranch became his happiness again.

The road to the 1933 Pony Bridge near Bridgeport was cracked and bumpy. Scenery shifted from flat and brown to green and purple scrub-brush-covered red dirt hills. The span was closed, but they watched the transition in reverse as Route 66’s landscape changed.

Museums became the day’s ambition. Papa Bob climbed 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.

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

Their evening ended in Amarillo, a piece of the writer’s heart. Her granny lived there with her dad’s sister. Susie. and Susie’s husband. John. for the last decade of her life. The writer had delayed telling Susie they might visit because she didn’t want to raise hopes. Susie died two months before the trip was approved.

John met Robbie at his first Christmas but had never seen Tommy. The writer described it as unfair that Susie wasn’t there to stand beside them and wave goodbye as they left.

In Amarillo, Uncle John showed the boys his horse, Levi, and taught them how to feed him.

From sunrise art to pie that comes with an ending

Cadillac Ranch at sunrise became another kind of permanence. Robbie, Papa Bob, John and the writer walked along a dirt path and applied their names and the year in a layer of light blue spray paint—permanently adding their journey to the art installation.

In Adrian, Texas, Midpoint Cafe and Gift Shop brought cherry cobbler. Owner Brenda Hammit Bradley told the writer she plans to sell at the end of the year. “I love this place, but I’m 65 years old and I’m tired,” Bradley said. “I make a lot of pie and if I never saw another pie pan again. I would be a happy lady.”.

New Mexico’s Route 66 was often under the interstate or on dirt roads. The family would have taken them but didn’t, choosing to rely on a rental minivan they weren’t fully ready to test.

Tucumcari’s murals. neon signs and the Blue Swallow Motel gave the trip its color. while the Mesalands Community College’s Dinosaur Museum kept the boys entertained with fossils and bronze skeletons. The family passed Owl Rock and Dead Man’s Curve on Laguna Pueblo land and described it as heartbreaking to see the mesa blasted through to build the four-lane Route 66. which eventually became Interstate 40.

From sagebrush to stuffed animals: ice cream twice, then again

There were creatures everywhere. In Albuquerque, the Rattlesnake Museum lived up to Robbie’s expectations, especially when one rattled its tail.

The family stopped for ice cream at Dairy Queen. a childhood tradition the writer’s dad continued with his three other grandsons. but hadn’t yet done with the boys. In Gallup. dinner came with free scoops of ice cream. and they almost said no—until the writer pointed out that the day the kids got ice cream twice might become one of their favorite memories from the trip.

Arizona to the Grand Canyon: fear, bargaining, and a shuttle back

At Petrified Forest National Park, the Painted Desert became “a-maz-ing” to Robbie. John nearly drove off the road at the sight of the blue mesa.

The writer tried not to get misty-eyed as the boys chattered at Papa Bob while hiking the Crystal Forest, another first. They did the touristy thing in Winslow, Arizona, standing on the corner. They also 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 ended with a pile of crayon drawings for Nana’s refrigerator.

At the Grand Canyon. Tommy asked if it was the giant “normous Canyon.” For hours. he reassured the writer he wouldn’t jump in. then walked toward the edge. Finally, her heart couldn’t take it. She said they took the shuttle back and drove the park themselves. Her fear of heights quickly disappeared when Tommy napped.

“It really gets to you,” the father said, recalling his own last visit at age 18 when he thought he could hike down and camp until a ranger asked for his permit.

What it means to preserve: dirt road history and a woman asking a question

In Seligman, Arizona, the family saw the legacy of dirt, brick and asphalt under the existing road. The writer described it as the place where Angel Delgadillo fought to save his hometown after I-40 bypassed it, helping protect the highway nationwide.

Seated in her father’s barber chair, Mirna Delgadillo, 62, said preserving Route 66 protects history. “Do we know where we’re going, if we don’t know where we came from?” she asked.

The “sidewinder” road climbed 3,550 feet through the Black Mountains, twisting through blind hairpin turns.

In Oatman, an old gold mining town, donkeys followed tourists along boardwalks and into stores. Nana fed the donkeys grass pellets, sold for a dollar a bag, and Tommy named them. Robbie found his souvenir: a rattlesnake stuffie in a can. and Papa Bob had a can opener to spare the family hours of listening about it.

In between the play and the stops, a family comment landed like a thread pulled through everything that came after. The writer joked over the walkie-talkie about camping beneath a jagged roadside monolith. Her mom replied, “You are your father’s daughter,” adding that he said the same.

California: waves, whoopee cushions, certificates, and the end that hurts

Along the Mojave Desert, the writer said she was struck by how much of the country—cities, ghost towns, small towns, mountains and prairies—had crossed in just two weeks.

At Roy’s Motel and Cafe in Amboy, the kids started to argue. The family rolled down the window and stuck out a hand to ride the wind. At Wigwam Motel in San Bernardino, the writer said they ran around the teepees. Papa Bob jumped in the pool with them.

In the Los Angeles area, the game shifted. Instead of shouting “cow” or “horse,” the boys shouted whenever they saw a palm tree. At Fair Oaks Pharmacy in South Pasadena. they grabbed pre-lunch ice cream and the boys played with whoopee cushions and Slinkys from the writer’s childhood. Nana bought shark and snake hand puppets as gifts.

At the Santa Monica Pier ending point, the line moved quickly. They were impatient to walk out to the waves. Ian Bowen, described as the “66 to Cali operator,” filled out their certificates of completion.

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

To mark the end. Nana and Papa Bob splurged on a whale spotting tour. the same tour they took with two other grandsons 15 years earlier. The writer described Nana and the boys leaning against the railing as a fin whale exhaled. Robbie yelled, “There, it’s there!” Tommy and the writer peeked through the railing as the whale came up again.

Robbie spoke with the naturalist, who pulled bottles of krill and whale poop from pockets. Robbie then declared himself an oceanographer and announced himself as a whale expert. Tommy cozied between Nana and Papa Bob while munching from a tub of popcorn.

When Route 66 came to a close, the writer said she finally understood the emotional pull it has had on so many Americans. She described a moment that landed quietly but decisively: she didn’t want her kids to cry, but she did want them to love.

Robbie and Tommy hugged Nana and Papa Bob goodbye. As the family walked away, Robbie ran back in tears for another hug.

“I didn’t know until that moment that a hug was what I was hoping for from the trip,” the writer said. She added that she had been the emotional kid who sobbed when leaving her granny and Aunt Susie behind in Amarillo—her dad saying it was proof she loved them, and telling Robbie the same.

Route 66 anniversary Chicago to Santa Monica American road trip family travel Route 66 history neon signs Grand Canyon