By Marisa McInturff & Greg Drevenstedt
Throughout its 100‑year history, Route 66 has been constantly realigned, reshaped, and reimagined. It was an official U.S. highway for a dozen years before it was entirely paved. And just a few months ago, the starting point for what is now Historic Route 66 in Chicago was moved 2 miles to the Navy Pier (see Kickstarts on page 9).
The evolution of Route 66 parallels the remarkably history of America throughout most of the 20th century and into the 21st century: from the Depression to World War II, from the economic prosperity of the 1950s to the space race of the 1960s, from the challenges of the 1970s to the modernization of the 1980s, when U.S. Route 66 was officially decommissioned. The past few decades of evolution have been about preservation and revitalization.
Route 66 has a reputation for being one highway, a single line on the map stretching from Chicago to Santa Monica. The reality is far more interesting. For much of its life, Route 66 was not a single road but a living network of evolving alignments which have been rerouted, straightened, bypassed, and sometimes abandoned entirely as America’s transportation needs changed.
When the highway was commissioned in 1926, it stitched together existing state and local roads rather than carving an entirely new path. That meant early Route 66 was often indirect, following the contours of towns, farmland, and terrain. It bent into communities instead of skirting them, which is what made it economically powerful. Every turn brought travelers past gas stations, cafes, and motor courts that depended on the steady flow of cross‑country traffic.
But roads change, and Route 66 changed faster than most.
By the 1930s and 1940s, increasing traffic volumes and the push for faster interstate travel began to reshape the highway. Engineers straightened curves, bypassed crowded downtowns, and shifted the route onto newer pavement where available. After World War II, this process accelerated. Entire segments of U.S. 66 were relocated to improve safety and efficiency, leaving behind long stretches of “old road” that quietly slipped into local use – or simply faded away.
By the time the Interstate Highway System arrived in 1956, Route 66’s fate was sealed. Interstates 55, 44, 40, and 15 gradually replaced it, and in 1985 the highway was officially decommissioned. But even before that final designation, Route 66 had already become a patchwork of original alignments, second‑generation re‑routings, and modern bypasses all coexisting across eight states.
For today’s traveler, that layered history is exactly what makes Route 66 so compelling.
Following Route 66 isn’t as simple as picking a single road and staying on it. In many places, there are multiple alignments to choose from, each offering a different version of the story. The earliest paths often run closest to the original 1920s route with narrow, winding, and broken pavement remnants that pass directly through small towns and forgotten stretches of countryside. Later alignments tend to be smoother and faster, built to accommodate postwar traffic, with wider shoulders and fewer interruptions. Some sections are just parts of what we now know as the interstate system.
Neither version is “correct.” They are simply different chapters.
Follow an early alignment, and you’ll often find yourself on quiet backroads where time feels compressed. These are the sections where you might cross a one‑lane bridge still bearing Route 66 signage or roll across brick pavement laid nearly a century ago. The pace is slower, the navigation more deliberate, and the reward is immersion in the road’s earliest form.
Stay on a later alignment, and you’ll experience the highway as mid‑century America knew it – streamlined, practical, and built for movement. These routes often pass just outside of towns rather than through them, which means fewer preserved neon signs and historic buildings but more continuous riding and a clearer sense of how Route 66 functioned as a national corridor.
The real magic happens when the two intertwine.
In states like Illinois, Missouri, Oklahoma, and Arizona, you can still ride sections where original pavement runs parallel to later bypasses – sometimes within sight of each other. One road carries the ghost of early cross‑country travel; the other reflects the modernization that replaced it. Choosing between them is about which version of the story you want to experience.
That’s why Route 66 is often described as an archive. Every detour, spur, and abandoned segment represents a decision point in American transportation history. And for riders willing to explore beyond the most direct path, those decisions are still visible on the landscape.
Scan the QR code to view an interactive map that shows the final alignment and older alignments of Route 66.
There are plenty of places along Route 66 where you can admire history. The Auburn Brick Road is one of the few places where you can actually ride on it.
Stretching for just over a mile south of Auburn, Illinois, this preserved section of original Route 66 offers a rare opportunity to experience the Mother Road much as travelers did nearly a century ago. Built in 1921, the road remains surfaced with thousands of red bricks laid by hand.
At first glance, the road doesn’t look particularly dramatic. Central Illinois isn’t known for towering mountains, deep canyons, or endless curves. Instead, the landscape is defined by rolling farmland, wide‑open skies, and a horizon that seems to stretch forever.
Approaching Auburn from Springfield, the route follows a classic stretch of Illinois Route 4 through rich agricultural country. Grain elevators rise above small towns, tractors move methodically through fields, and the pace of life feels refreshingly unhurried. It’s easy to imagine what cross‑country travelers experienced when Route 66 served as America’s Main Street.
The brick section begins just south of town. Modern pavement abruptly gives way to rows of weathered red bricks that have carried generations of automobiles, trucks, and motorcycles westward. The transition is immediate. Tire noise changes. The handlebars transmit a subtle vibration. Even at moderate speeds, you become more aware of the machine beneath you and the history beneath the tires.
The Auburn Brick Road is listed on the National Register of Historic Places and remains one of the best‑preserved original Route 66 road segments anywhere in the country. While many historic stretches have been bypassed, widened, or paved over, this section survives largely intact thanks to preservation efforts and the dedication of local Route 66 advocates.
Most riders will find themselves making multiple passes. The road is short, but that’s hardly the point. The experience is less about distance and more about atmosphere. Pull off for photos, walk among the bricks, and take a moment to appreciate the craftsmanship that went into building roads before modern paving equipment existed.
The nearby town of Auburn embraces its Route 66 heritage, making it a convenient stop before continuing north toward Springfield or south toward Litchfield and the many roadside attractions that define this section of the Mother Road. Vintage gas stations, historic diners, and quirky roadside landmarks are never far away.
Located between Miami and Afton in northeast Oklahoma, this narrow surviving piece of original Route 66 feels like a time capsule poured in concrete. At just nine feet wide, it’s narrower than many modern traffic lanes. Ride onto it, and the first impression isn’t speed or scenery; it’s perspective. Suddenly, you understand how different early American road travel really was.
Built in the early 1920s, before Route 66 officially existed, the Ribbon Road was born from practicality and tight budgets. Engineers wanted to connect rural communities but didn’t have the money for a full‑width highway. The solution was simple: pave a single nine‑foot strip of concrete across the countryside and let drivers sort out the details. When vehicles met head‑on, somebody eased onto the dirt shoulder.
The surviving stretch begins quietly in Ottawa County, tucked into Oklahoma farmland not far from the Kansas and Missouri borders. There’s no dramatic mountain backdrop or canyon scenery here. Instead, the landscape is classic northeastern Oklahoma with rolling pastureland, scattered trees, and expansive skies.
The route flows gently through the countryside without demanding technical riding skills. But the narrow pavement changes the way you think about space. On a motorcycle, the road feels intimate in a way modern highways rarely do. You’re aware of your line placement, the abrupt pavement edge, and the ghost of a transportation system still figuring itself out.
Every mile of the Ribbon Road carries the atmosphere of early automotive America, an era when cross‑country travel was adventurous, unpredictable, and often uncomfortable. Imagine touring riders in leather helmets, dust clouds rising from shoulders, and travelers in overloaded sedans chasing California dreams down a highway that barely qualified as wide enough.
The concrete itself becomes part of the experience. You can still see the character of the original surface, the subtle imperfections and aged texture that separate it from modern blacktop efficiency. Historical markers along the route help frame what you’re seeing, but the road explains itself.
Few places on Route 66 allow riders to physically experience infrastructure from the Mother Road’s earliest years quite like this.
In its original alignment, Route 66 through New Mexico stitched together parts of two road networks. As it entered New Mexico from Texas, it followed one of the main routes of the Ozark Trail through Tucumcari and Santa Rosa then north to the small town of Las Vegas. As it continued west, it followed the National Old Trails Road, a U‑shaped path that dipped south and then north to Santa Fe through the Sangre de Cristo Mountains and then south again to Albuquerque, Los Lunas, and Isleta Pueblo before continuing west toward Arizona.
The original routing through Santa Fe was anything but a straight line. Route 66 followed an irregular S‑shaped curve, and it went over Glorieta Pass, which marks the southern terminus of the Rocky Mountains and was the site of a Civil War battle in 1862.
On Nov. 2, 1926, six months after Route 66 was officially assigned the number “66” by federal officials and just nine days before the U.S. numbered highway system was adopted and mapped, Arthur T. Hannett, the Democratic governor of New Mexico, lost a bitter gubernatorial campaign to Republican challenger Richard Dillon.
At the time, there was no direct route between Albuquerque and Santa Rosa. You either had to go north through Santa Fe or south through Encino and Mountainair. Dillon ran a profitable sheep‑shearing and meat‑production operation in Encino. With Route 66 on the horizon and not wanting increased traffic to enrich his rival, Hannett used his lame‑duck power to get revenge.
Hannett, who remained governor until Dillon took office on Jan. 1, 1927, enlisted the state highway department to survey, cut, scrape, and grade a 69‑mile road that would provide a direct east‑west route between Albuquerque and Santa Rosa. Working around the clock – through the harsh winter and not taking time off for Christmas – and despite attempts by Dillon sympathizers to sabotage equipment, the workers completed the job in just one month. The rushed project came to be known as “Hannett’s Joke.”
Route 66 followed its circuitous path through Santa Fe from 1926 until 1937. Once federal funding allowed the entire route to be paved, Route 66 officials adopted a realignment that followed the more direct east‑west route between Albuquerque and Santa Rosa, cutting off about 100 miles from the original route. The shorter alignment was gradually replaced by Interstate 40 from the 1970s until U.S. Route 66 was decommissioned in 1985.
We are grateful to Eric Scott Jeffries for providing historical insights about “Hannett’s Joke” in his Spring 2000 article in New Mexico Bar Journal.
Arizona’s Oatman Highway, which winds its way through the Black Mountains between Kingman and the California border, is one of the best‑known lost alignments of Route 66.
This original part of Route 66 was renowned as the most treacherous section of the entire 2,448‑mile highway. In particular, the 8‑mile stretch from Cool Springs to the former mining town of Oatman had a reputation for danger and hardship. Known today at the “Arizona Sidewinder,” this section of old Route 66 slithers through 191 curves, including numerous switchbacks, on a narrow roadbed with precipitous drop‑offs and no guard rails. The road climbs up to 3,550‑foot Sitgreaves Pass and then plunges down the other side. Steep grades taxed the radiators, tires, and brakes of early cars and trucks, as well as the nerves of many drivers, leading some travelers to pay experienced locals to drive their vehicles over to Oatman.
In John Steinbeck’s novel The Grapes of Wrath, Oatman Highway was the final challenge before the weary Joad family reached California: “They drove all night, and came to the mountains in the night. And they crawled the jagged ramparts in the night, and their dim lights flickered on the pale stone walls of the road. They passed the summit in the dark and came slowly down in the late night, through the shattered stone debris of Oatman; and when the daylight came they saw the Colorado river below them.”
Oatman Highway remained an obstacle to overcome on Route 66 from 1926 until 1952, when a new alignment followed a straighter, flatter path from Kingman to Yucca and on to the state line, the route now followed by Interstate 40.
Today, Oatman Highway is a bucket‑list destination for motorcyclists traveling on Route 66. Cool Springs Station and Oatman, famous for its burros, are popular stops for riders and other tourists passing through western Arizona. The road’s rough pavement, tight curves, and steep grades will challenge any rider, and from late spring through fall, daytime temperatures can easily top 100 degrees, so it pays to stay alert and be prepared.