One Century, One Road
Route 66, ‘The Main Street of America,’ turns 100
By Jonathan Bullington and E. Jason Wambsgans
It was created to connect us, a fused chain of existing roadways many unpaved that stretched 2,448 miles across eight states and three time zones, starting steps from Lake Michigan in downtown Chicago and ending near the Pacific Ocean and Santa Monica’s famed fishing pier.
Route 66, “The Main Street of America.”
There is perhaps no better-known highway anywhere in the world. In its 100-year history, it has offered safe passage to Dust Bowl refugees, World War II transports and vacationing families. John Steinbeck called it “the mother road, the road of flight.” Nat King Cole crooned about its kicks in a 1946 hit song. Disney and Pixar took inspiration from it for a 2006 blockbuster.
The famed highway conjured images of quirky roadside attractions, mom-and-pop diners, neon-signed motels and art deco service stations. Each mile promised freedom, escape, adventure, exploration. It introduced countless Americans to their country, to vast lands that previously existed only in the collective imagination.
Despite being decommissioned in 1985 in favor of a faster and wider interstate highway system, Route 66 continues to capture our imaginations in the remnants of its past glory that remain today.
Now, Route 66 boosters in all eight states (Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California) are gearing up to celebrate the iconic route on its centennial in 2026.
Ahead of next year’s anniversary, the Chicago Tribune will set out across Route 66 to introduce readers to the people and places it was designed to connect the entertaining characters and roadside oddities, the business owners trying to revitalize their pieces of history and the voices that had been previously obscured in the roadway’s lore.
In pursuit of the unknown, we’re starting our journey at the farthest point from home, in Santa Monica, and working our way back to Chicago.
Along the way, we’ll explore whether the highway still has the power to unite a deeply divided country and learn what it has to tell us about the current state of our nation.
What does Route 66 mean to you?
Stop No. 1: The end of the road at Santa Monica pier
Our Route 66 road trip began at the end, at the famed fishing pier jutting out into the Pacific Ocean. On a breezy Sunday afternoon, the first day of June, a steady stream of visitors waited their turns to pose with one of the pier’s most popular attractions: a Route 66 sign, perched on a pole 12 feet above the wooden planks, advertising the spot as the “end of the trail.” Read more here.
Stop No. 2: Visiting a desert ghost town
Water is the key to the future of Roy’s Motel & Cafe, the lone survivor in a Route 66 town that, at its peak, boasted 200 residents, three gas stations, three motels, two cafes, a post office, a school and a church.
Then Interstate 40 came a half-century ago and offered travelers a faster way through this remote stretch of the Mojave Desert in eastern California. “It was like they turned off the cars,” said Roy’s manager, Ken Large. “Everybody just left.” Read more here.
Stop No. 3: The Arizona Sidewinder, wild burros and a living statue
There is a roughly 8-mile section of Route 66 at the western edge of this state that is considered to be one of the most scenic and white-knuckled drives this country has to offer. It’s known as the Arizona Sidewinder, or to locals, simply, The Sidewinder. Read more here.
Stop No. 4: A rainy day at the Hackberry General Store
The mayor stretched on the couch under the air conditioner in the Hackberry General Store and looked slightly annoyed at the tourist who woke him from his nap.
In addition to his duties as the unofficial leader of the unincorporated former mining town’s 334 residents, Charlie the 10-year-old cat is also the store’s night security guard and its exterminator.
“He was dropped off as a kitten,” remembered store clerk Eva Rodriguez, 66. “He was feral, just a mess. But he decided he liked this place.” Read more here.
Stop. No. 5: Meet the Mother Road’s ‘Guardian Angel’
They came suddenly and in numbers, cars and trucks weighed down with their owners’ worldly possessions. Angel Delgadillo was a boy when those hundreds of thousands of Dust Bowl refugees drove through his tiny hometown on Route 66, heading for California and the promise of work on farms so fertile, it was said, that fruit fell from the trees.
He and his friends used to run to a nearby building at night and wait for the passing vehicles’ headlights to cast their shadows on the white stucco wall. They danced and watched their shadows change as the cars neared.
“And as a car left,” he remembered, “our shadows went with them.” Read more here.
Stop No. 6: In Albuquerque, a $13 million visitors center and a neighborhood in peril
This probably isn’t the Route 66 that most people imagine. Here, there are no restored 1950s diners or art deco gas stations-turned-gift shops.
Here, homeless encampments occupy an entire city block, and it is not uncommon to see people openly injecting drugs while sitting on a curb.
This neighborhood that surrounds this roughly 2-mile stretch of Route 66 in New Mexico’s largest city goes by two names. Read more here.
Stop No. 7: Illinois ties to the devil’s rope, an infamous gap and a Texas-sized challenge in the Panhandle
Route 66 extends nearly 180 miles across the Texas Panhandle, starting in the ghost town of Glenrio, which straddles the border between Texas and New Mexico. About 20 miles east, the town of Adrian advertises itself as the route’s midpoint, equidistant to Chicago and Los Angeles.
The road passes vast farm fields, undulating grasslands dotted with towering wind turbines and sprawling cattle ranches before entering Amarillo, the Panhandle’s largest city. At its western edge sits one of Route 66’s most photographed attractions: Cadillac Ranch. Read more here.
Stop No. 8: Feeling less alone at an Oklahoma ‘No Kings’ protest
Few, if any, thought they were going to change minds by standing on a patch of grass along Route 66 and holding signs decrying Donald Trump’s presidency. All 77 Oklahoma counties voted to return him to the White House. Here in Beckham County, at the state’s western edge, he carried 84% of the vote.
Still, many of the 40 people who gathered Saturday for Elk City’s piece of the nationwide “No Kings Day” protests said, at least for that moment, they felt less alone.
“When you live in a rural area and you’re a blue dot, you can feel very isolated,” said Shelly Larson, 61, a native Oklahoman who has been counted among the town’s 11,000 residents for the last five decades. “Just knowing there are others, it’s good for the soul.” Read more here.
Stop No. 9: Hamburgers so savory, they can make you cry
The air downtown smells of grilled onions, wafting from the flat tops of three Route 66 restaurants that have helped give this small town about 25 miles west of Oklahoma City a distinct culinary identity.
They’re called fried onion burgers. Plenty of places put onions on burgers. Few have been doing it as long, or as well, as they do here.
“They’re not like any burger,” said Lyndsay Bayne, 48, the city’s public information and marketing manager. “It’s hard to explain. You have to eat one.” Read more here.
Stop No. 10: Print day at a 145-year-old Kansas newspaper
The newspaper has existed in one form or another in this part of southeastern Kansas since 1880, three years after the town was founded around the discovery of lead in the area. Its current iteration is the result of a 1945 merger between The Galena Times Republican and The Galena Sentinel. Read more here.
Stop. No. 11: In St. Louis, a deadly twister crosses a long-standing divide
There was no warning siren, only the sudden sound of what seemed at first like a locomotive speeding through her neighborhood a mile off Route 66.
Lea Davis heard trees snapping. Glass shattering. The front door to her 122-year-old two-flat slammed open and shut. Open and shut. She thought to grab her partner, Reginald, who is blind, and run to the basement, but figured they might not make it in time. They could take shelter in the closet, she thought, or the bathtub.
“You didn’t have much time to think,” Davis, 55 remembered of that May 16 afternoon. “The only thing I could say was: Jesus, please save us. Please help us.” Read more here.
Stop. No. 12: The last (or first) 300 miles in Illinois
Our Route 66 road trip ended at the beginning, at East Jackson Boulevard and South Michigan Avenue in Chicago, where a brown sign hanging 12 feet high on a light post tells people they’ve reached the venerable road’s threshold.
While the route often conjures images of quaint small towns, its foundation, said historian and author Jim Hinckley, has always been rooted in Chicago. The existing roads and trails that would eventually become Route 66 nearly 100 years ago largely followed the railroad, with Chicago as its hub. Read more here.