The morning of July 7th, 1919, a young lieutenant colonel named Dwight Eisenhower stood on the Ellipse in Washington, D. C. , and looked over a convoy of eighty-one military vehicles that stretched out before him like a steel serpent. He was twenty-eight years old, fresh from training tank crews in Pennsylvania, and he had volunteered for this assignment because it sounded like an adventure.

The United States Army had decided to drive a full military convoy from Washington all the way to San Francisco, roughly following the route of the Lincoln Highway, to find out whether the army could actually move itself across its own country. Eisenhower climbed into his vehicle, the order was given, and the convoy rolled past the White House, heading west. It took them seven hours to cover the first fifty miles. That alone should have told them what they were in for.

To understand why the convoy was moving so slowly, you have to understand what America looked like in those years. In 1903, the country had roughly 2. 3 million miles of road. That number sounds impressive until you learn the next detail: fewer than 150 miles of those roads were paved.

Everything else was dirt, gravel, mud, planks, or whatever the local county could scrape together. Most of these roads had been built not for cars, which barely existed, but for farmers hauling grain to the nearest railway depot. The entire transportation infrastructure of the United States was oriented around the railroad. If you wanted to go from Chicago to San Francisco, you bought a ticket and sat in a Pullman car for four days.

If you wanted to travel across your home state, you probably took a train. Roads existed to get people and goods from the farm to the station. That was the entire design philosophy. Long-distance road travel wasn’t just difficult.

It was unthinkable. Then the automobile arrived, and suddenly a small group of wealthy, restless Americans started asking a dangerous question. If I own this machine, why can’t I drive it anywhere I want? One of those restless Americans was a Vermont physician named Horatio Nelson Jackson.

In May 1903, Jackson was visiting San Francisco with his wife. He was thirty-one years old, well-off, and he had the kind of personality that gets a man into trouble at dinner parties. One evening at the University Club, Jackson got into an argument with a group of men about the future of the automobile. The consensus around the table was that cars were a toy, a passing fad, a plaything for the rich that would never amount to anything practical.

Jackson disagreed. He insisted that a car could be driven across the entire United States. The men laughed. Someone proposed a wager: fifty dollars, which was real money in 1903.

Jackson accepted on the spot. He had ninety days to drive from San Francisco to New York City in an automobile. He had no mechanic, he had no map, he didn’t even own the car he was going to use. He just had his word, a borrowed sense of mission, and that burning need to prove the room wrong.

Jackson bought a used 1903 Winton touring car, a stripped-down two-seater with twenty horsepower, and nicknamed it the Vermont. He hired a mechanic named Sewall Crocker to come along, loaded the car with camping gear, spare parts, extra fuel, rifles, and a block and tackle for pulling the car out of ditches. On May 23rd, 1903, they rolled out of San Francisco heading north. They had to go north because the Sierra Nevada mountains were impassable to an automobile.

Within fifteen miles of leaving town, they blew their first tire. By the time they reached Oregon, Jackson had already learned that the real enemy wasn’t the car. It was the complete absence of anything resembling a road network. They crossed rivers that had no bridges.

They were misdirected by a woman in northern California who sent them more than a hundred miles out of their way just so her family could see their first automobile. They slept outdoors. They ran out of food. In Idaho, Jackson bought a bulldog named Bud for fifteen dollars, strapped a pair of goggles onto the dog, and Bud rode shotgun for the rest of the trip.

They forded streams. They begged gasoline from farmers. And along the way, something happened. The Winton and Oldsmobile companies back east heard about Jackson’s attempt and decided to send their own cars across the country to beat him.

Suddenly there were three cars crawling across the United States at once, all racing to be the first to make it to New York. Jackson didn’t know any of this until the Packard and Oldsmobile teams started catching up to him in Wyoming. The press began following along, telegraphing updates to newspapers in the big cities. What had started as a dinner-party bet had turned into the first great American automobile race.

Jackson, Crocker, and Bud finally pulled into New York City on July 26th, 1903, sixty-three days, twelve hours, and thirty minutes after leaving San Francisco. They were the first people to drive an automobile across the United States. Jackson never actually collected the fifty dollars. The trip had cost him somewhere around eight thousand dollars, which in today’s money is well over a quarter of a million.

He didn’t care. He had proved that the automobile was not a toy but a machine that could cross a continent. And if one Vermont doctor and his mechanic and a bulldog could do it, then eventually millions of other Americans could too. The problem was still the roads.

Jackson’s trip had worked only because he treated it as a kind of military campaign, carrying everything with him and begging the rest from strangers. Nobody could do that casually. In the decade after Jackson’s drive, a handful of other adventurers made the crossing, each one shaving a few days off the previous record. By 1916, a team of professional drivers using relay crews got the time down to five days.

But those were stunts. For the average American who owned a Ford Model T, which Henry Ford had put into mass production in 1908, driving from one state to the next was still a serious undertaking. And driving coast to coast was essentially impossible. Something had to change.

Someone had to actually build roads. The man who first saw that opportunity and seized it with both hands was a hyperactive, half-blind, chain-smoking Indiana entrepreneur named Carl Fisher. Carl Graham Fisher is one of those enormous American characters that history has allowed to fade from memory. In the span of about three decades, Fisher built an empire out of practically nothing.

He started out as a bicycle shop owner in Indianapolis in the 1890s, moved into selling cars when the automobile boom began, co-founded the Prest-O-Lite company that made the carbide headlights that allowed cars to drive at night, built the Indianapolis Motor Speedway, where the Indy 500 is still run every year, and later single-handedly developed Miami Beach from a mangrove swamp into one of the most famous resort cities in the world. He was a born promoter. He once rode a bicycle across a tightrope strung between two buildings in downtown Indianapolis to drum up business for his shop. He strapped a car to a hot-air balloon and let it float above the city.

Everything Fisher touched turned into publicity, and most of it turned into money. In 1912, Fisher got what he believed was his biggest idea yet. He wanted to build a rock highway all the way across the country from New York to San Francisco. On September 10th, 1912, he proposed the idea at a dinner meeting with his friends from the auto industry.

He called it, at first, the Coast-to-Coast Rock Highway. The pitch was simple: the automobile industry depended on good roads, and without good roads, nobody would buy cars for anything other than tooling around town. The auto companies themselves ought to pay to build a decent road as a giant marketing project to prove that long-distance driving was possible. Fisher wanted ten million dollars in donations from the automobile industry.

He got pledges from Frank Seiberling of Goodyear and Henry Joy of Packard Motor Car Company, who became the first president of the organization they formed to manage the project. The road was named the Lincoln Highway in honor of Abraham Lincoln, after Congress rejected a competing proposal to build a Lincoln Memorial Highway from Washington to Gettysburg. On July 1st, 1913, the Lincoln Highway Association was formally established, with the stated goal of building a continuous improved highway from the Atlantic to the Pacific, open to lawful traffic of all description without toll charges. On October 31st, 1913, the Lincoln Highway was formally dedicated.

It became America’s first national memorial to Lincoln, predating the Lincoln Memorial in Washington by nine years. Here is where the story gets a little bit absurd. The Lincoln Highway was not really a road, not in the sense we would recognize today. It was a route.

The association picked out a path from Times Square in New York City to Lincoln Park in San Francisco, running through thirteen states and measuring 3,389 miles end-to-end. But the actual road surface for most of that distance was whatever had already existed: dirt tracks, wagon ruts, short sections of gravel. The association put up signs with the Lincoln Highway logo, a red, white, and blue stripe with the letter L in the middle, and painted that logo onto poles, barns, and fence posts along the way so that drivers could follow the route. In some places, especially out west, the highway was literally just a line drawn on a map through empty desert.

The Lincoln Highway’s own publicity materials cheerfully warned motorists to carry chains, shovels, extra tires, cans of gasoline, drinking water, and a good deal of patience. Still, the idea caught fire. Within a few years, the Lincoln Highway had become the most famous road in America, and other promoters started piling on with their own named highways. Carl Fisher himself immediately launched a second one, the Dixie Highway, running from Michigan down to Miami.

Then came the Jefferson Highway from New Orleans to Winnipeg, the Yellowstone Trail from Plymouth, Massachusetts to Seattle, the Old Spanish Trail from St. Augustine to San Diego, the National Old Trails Road, the Bankhead Highway, the Atlantic Highway. By the mid-1920s, there were hundreds of these named auto trails crisscrossing the country, each one promoted by its own private association, each one with its own distinct colored stripes painted onto roadside objects, and each one competing for the attention of American motorists and the dollars of the small towns along the way. The result was a system that worked beautifully right up until the moment you tried to actually use it.

Imagine driving along a telephone pole with eight different colored bands painted on it, each representing a different highway, each pointing in a slightly different direction. Imagine trying to figure out whether the yellow stripe meant the Yellowstone Trail or the Jefferson Highway or something else entirely. Imagine arriving in a small Iowa town and asking a local which road to take to get to Omaha, only to be told that it depended on which highway association you had joined. The whole system was chaos.

Worse, many of these trail associations were little more than scams. They would collect dues from towns in exchange for routing the highway through them. Some of these highways existed only on paper, mapped out across territory that had no actual roads at all. In 1925, the chief engineer of the US Bureau of Public Roads wrote in disgust that in nine cases out of ten, these transcontinental highway associations are common nuisances and nothing else.

Meanwhile, the federal government was slowly starting to take notice. In 1916, President Woodrow Wilson signed the Federal Aid Road Act, which for the first time provided fifty percent federal matching funds to help states improve their roads. The money was modest and the stated purpose was mostly to help the Postal Service deliver rural mail more reliably. But it was the first step toward a federal role in building the American road network.

Then came World War I. The war shifted enormous amounts of goods onto the nation’s rail lines, overwhelming them, and the army started experimenting with moving supplies on rubber tires using trucks. The experience taught military planners that American roads were a national security disaster waiting to happen. If you couldn’t move an army across your own country, you were in trouble.

That realization set up the summer of 1919. In Pennsylvania, the roads were tolerable. In Ohio, they were worse. In Indiana and Illinois, they were deeply rutted dirt.

In Iowa and Nebraska, the convoy slowed to a crawl. Bridges collapsed under the weight of the heavier trucks and had to be rebuilt by advance teams before the convoy could pass. Trucks sank into mud up to their axles and had to be winched out, sometimes for hours at a stretch. In one particularly nightmarish stretch of Utah, the vehicles hit a patch of quicksand, and it took the soldiers seven hours to drag the convoy through just 200 yards of road.

They crossed deserts where they ran out of water and had to ration it among the men. They logged more than 230 serious incidents of mechanical failure, accidents, or vehicles getting stuck. They arrived in San Francisco on September 6th, 1919, after sixty-two bone-jarring days on the road. The total distance covered was 3,251 miles.

The average speed was about six miles per hour. The convoy was six days behind schedule. Eisenhower wrote a detailed report when he got home. He was polite but blunt.

The roads were terrible. The bridges were worse. The country’s ability to move its own military across itself was essentially zero. He noted that the men of the convoy had become firm believers in the need for a national system of good highways.

He filed the report and more or less filed away the experience as well, since he had a career to focus on and no obvious way to translate his frustration into action. But he would remember it very clearly for the rest of his life. And eventually, decades later, he would do something about it. The 1919 convoy helped push Congress to pass the Federal Aid Highway Act of 1921, a significant expansion of the 1916 bill.

The 1921 Act limited federal aid to a specific network of major roads, no more than seven percent of each state’s road mileage, and required that at least three-sevenths of that network had to be interstate in character, meaning it had to connect to roads in neighboring states. For the first time, the federal government was effectively mapping out a national highway network, even if the states were still doing the actual building. By the mid-1920s, the chaos of the named highway system had become unbearable. State highway officials were drowning in requests from private associations to route their trails through particular towns.

Motorists were getting hopelessly lost on roads that had six different colored stripes. Something had to be done. In 1924, the American Association of State Highway Officials decided to design a national grid of numbered highways that would replace the named trails entirely. A joint board of twenty-one state highway officials and three Federal Bureau of Public Roads officials spent most of 1925 working out the details.

On November 11th, 1926, the United States numbered highway system was formally adopted. Every major road in the country would get a number. Odd numbers would run north-south, with low numbers in the east and high numbers in the west. Even numbers would run east-west, with low numbers in the north and high numbers in the south.

The signs would all look the same: a simple black and white shield with the US and the route number. No more colored stripes, no more guessing, no more scam trail associations collecting dues. Just a logical nationwide grid of numbered roads. The Lincoln Highway, which had been the most famous road in the country for thirteen years, was absorbed into the new system.

Most of it became US Route 30. The Lincoln Highway Association was dissolved in 1927, its mission essentially accomplished. The Dixie Highway was broken up among several US numbered routes. The Jefferson Highway disappeared into US 71 and US 61.

The named highway era was over. But out of that same 1926 reorganization emerged a road that would become the most famous highway in the world. In the planning stages, an Oklahoma Highway Commissioner named Cyrus Avery pushed hard for a diagonal route running from Chicago to Los Angeles, down through Missouri, Oklahoma, Texas, New Mexico, Arizona, and into California. Avery wanted the number 60 for his highway because he thought a round number would carry more prestige.

He lost that fight to another road that eventually became US 60, running from Virginia to Arizona. Avery and his allies settled on the next available round-sounding number, which happened to be 66. Nobody at the time thought it was a particularly important choice. US Route 66 was officially commissioned on November 11th, 1926.

It ran 2,448 miles from Chicago to Santa Monica. In 1926, large sections of it were still gravel or dirt. It would not be completely paved until 1938, making it the first fully paved US highway in the country. But from the moment it was born, Route 66 started to work its way into the American imagination.

It cut diagonally across the country at exactly the angle that nineteenth-century migrants had followed to reach California. It wound through small towns that had no other reason to exist. It ran through the heart of the Dust Bowl. When the Depression hit in 1929 and the plains dried up and blew away in the mid-1930s, hundreds of thousands of farming families from Oklahoma, Arkansas, Texas, and Kansas loaded their belongings into old Model Ts and Model As and headed west on Route 66, chasing the dream of agricultural work in California.

John Steinbeck immortalized them in The Grapes of Wrath in 1939, where he called Route 66 the Mother Road, the road of flight. The nickname stuck. In 1946, songwriter Bobby Troup wrote the song that would make Route 66 permanently famous, telling listeners that if they ever plan to motor west, they should travel the highway that was best and get their kicks on Route 66. Nat King Cole recorded it that same year.

The road became a myth before most Americans had even driven on it. But Route 66 was still, in the end, a two-lane road. So was almost every other long-distance highway in America. If you were driving across the country in the 1930s, you were doing it on roads that passed directly through the main street of every town along the way.

You were stopping at red lights. You were slowing down for school zones. You were waiting behind farm trucks. You were sharing the pavement with horse-drawn wagons in some rural areas.

A coast-to-coast trip that today takes about three days of hard driving took the better part of two weeks. The economy that grew up around these highways was something that no previous generation had ever seen. If you were going to drive across the country, you needed places to eat, places to sleep, and places to fill up your tank. In the earliest years, people simply pulled off the road and camped.

They slept in tents in farmers’ fields. They cooked on open fires. By the early 1920s, so many motorists were doing this that farmers started complaining about the mess, and towns began establishing free municipal auto camps, usually near the center of town, where travelers could pull in, park, and spend the night. The town got the tourist dollars.

The farmers got their fields back. By the mid-1920s, private entrepreneurs figured out there was money to be made. The free municipal camps gave way to cabin camps, where you paid a dollar or two to stay in a tiny wooden cabin that was essentially a one-room shed. The cabin camps gave way to tourist courts, which were nicer cabins, usually arranged in a horseshoe or U shape around a central courtyard, with individual parking spots next to each unit.

The tourist courts became motor courts, which were essentially the same thing but with slightly better amenities, like running water and electric lights. By the late 1930s, the motor court had evolved into what we would recognize today as a motel, a word coined in 1925 by a California hotel owner named Arthur Heineman, who ran out of room on his sign for the words Milestone Motor Hotel and shortened it to Milestone Motel. By the 1940s, the American roadside was lined with thousands of these places, each one competing for the attention of passing drivers through increasingly elaborate neon signs, themed architecture, and roadside billboards. The same thing was happening with food.

The diner, the roadhouse, the drive-in, and eventually the fast food chain all evolved out of the need to feed motorists quickly and cheaply. Gas stations grew from being single pumps in front of general stores into dedicated service stations with uniformed attendants who would pump your gas, check your oil, wash your windows, and inflate your tires while you waited. Entire industries grew up overnight around the automobile. Rand McNally, which had been printing railroad maps for decades, started printing highway maps and selling them at gas stations, often giving them away for free as promotional items.

The American Automobile Association became the single most important source of trip planning information for American motorists, publishing triptychs that walked you through your route turn by turn. Through the Great Depression, road building actually accelerated because the federal government saw highway construction as the perfect way to put unemployed men back to work. The Civilian Conservation Corps and the Works Progress Administration poured millions of man-hours into paving roads, building bridges, carving mountain passes, and improving the shoulders of existing highways. Some of the most beautiful stretches of American road, like the Blue Ridge Parkway and the Going-to-the-Sun Road in Glacier National Park, were built during this period.

And then, on October 1st, 1940, something arrived in Pennsylvania that would change the entire conversation. The Pennsylvania Turnpike opened to traffic at one minute past midnight. It was 160 miles long, running from Carlisle in the east to Irwin in the west, cutting across the rugged Allegheny Mountains. It had been built using seven tunnels originally dug in the 1880s for the never-completed South Pennsylvania Railroad, which the industrialist William Vanderbilt had tried to build to compete with the Pennsylvania Railroad.

Vanderbilt had been forced to abandon the project under pressure from J. P. Morgan, and the half-finished tunnels had sat empty for more than fifty years, filling with water and overgrown with vegetation. In the late 1930s, Pennsylvania engineers realized they could use those abandoned tunnels as the backbone of a brand new kind of road.

What they built was unlike anything that had ever existed in America. The Pennsylvania Turnpike was a four-lane divided highway with a grassy median separating the eastbound and westbound traffic. It had no intersections, no stop signs, no traffic lights, no driveways. You entered the road at one of eleven designated interchanges and exited at another.

In between, you could drive as fast as your car would go. There were no speed limits on the Turnpike when it first opened. There were service plazas where you could pull off for gas and food without ever leaving the highway. The road had been designed by engineers who had traveled to Europe and studied the German Autobahn, which Adolf Hitler had been constructing since 1933 as part of his economic recovery program.

The Pennsylvania Turnpike was America’s answer, and the response was immediate and overwhelming. In the first week it was open, more than 150,000 vehicles drove on it. In the first year, five million cars used it, generating three million dollars in toll revenue. The Turnpike was advertised as America’s first superhighway, and the slogan was not an exaggeration.

But the Pennsylvania Turnpike was still just one road in one state. Across the rest of the country, drivers were still bouncing along two-lane highways and crawling through the main street of every town between them and their destination. World War II put most civilian road building on hold. During the war, though, something happened that would quietly set the stage for the biggest transformation of all.

Dwight Eisenhower, now a four-star general commanding the Allied Forces in Europe, got his first look at the German Autobahn system. He saw how fast military convoys could move on it. He saw how it bypassed cities instead of running through them. He saw how it was divided, limited access, and built to last.

He remembered 1919. He remembered sixty-two days to cross his own country. He remembered the quicksand, the broken bridges, and the trucks sinking in Nebraska mud. And he started to think.

When Eisenhower became president in January 1953, he began laying the groundwork for what would eventually become the Interstate Highway System. He formed internal committees, consulted with governors, and lobbied Congress. In his 1954 and 1956 State of the Union addresses, he called explicitly for a modern Interstate Highway System. The idea had actually been on the table for years.

The Federal Aid Highway Act of 1944 had authorized the creation of a 40,000-mile national system of Interstate Highways, but Congress had never actually funded the construction. For twelve years, the system existed only on paper. Eisenhower wanted to make it real. The debate in Washington wasn’t about whether to build the roads.

Nearly everyone agreed they were needed. The debate was about how to pay for them. The administration proposed a bond issue. Congress rejected it.

Instead, two Democratic lawmakers, Senator Albert Gore Sr. of Tennessee and Representative Hale Boggs of Louisiana, along with Representative George Fallon of Maryland, pushed through a bill that would fund the roads through a federal gasoline tax, with the money flowing into a dedicated highway trust fund that could only be spent on highway construction. On June 26th, 1956, both the House and the Senate approved the final bill. Three days later, on June 29th, 1956, Eisenhower, who was recovering from surgery at Walter Reed Army Hospital, signed the Federal Aid Highway Act of 1956 into law.

The official name of the system was the National Interstate and Defense Highways, with defense included partly because some of the funding came from defense appropriations and partly because the Interstate System was expected to serve as a military mobility network in case of war. The bill authorized the construction of 41,000 miles of new highway, with the federal government paying ninety percent of the cost. It was projected to cost about twenty-five billion dollars and to take thirteen years to complete. In reality, it would take thirty-five years to finish and would cost roughly 128.

9 billion dollars by the time the official system was declared complete in 1992. It would become the largest public works project in human history up to that point. The Interstate System didn’t just change how Americans drove. It changed everything about American life.

The small towns that had thrived along Route 66 and the Lincoln Highway and the dozens of other named roads suddenly found themselves bypassed, cut off from the stream of traffic that had kept them alive. Entire main streets dried up almost as quickly as the Dust Bowl towns had thirty years earlier. The motor courts and tourist cabins that had defined American road travel for a generation were replaced by chain motels built directly at Interstate exits. Local diners gave way to McDonald’s and Howard Johnson’s.

The idiosyncratic, hand-painted, neon-lit roadside Americana of the pre-Interstate era began a slow, decades-long disappearance that is still going on today. Route 66 itself was gradually bypassed, segment by segment, as Interstate 40 and other interstates took over the long-distance traffic. In 1985, the road was officially decommissioned from the United States Highway System, erased from the official maps, surviving today only as a nostalgia trail for tourists who want to experience what crossing America used to feel like. What was gained was almost incomprehensible.

By the 1960s, you could drive from New York to Los Angeles in about four days of hard driving, cruising at seventy miles per hour on four-lane divided roads with no stop signs, no intersections, and no delays. By the 1970s, a majority of American families had taken at least one cross-country road trip. The country shrank. Distances that had defined the American experience for three centuries suddenly didn’t matter in the same way anymore.

Freight that used to move by rail started moving by truck. Suburbs exploded because workers could now live twenty or thirty miles from the city and drive to work on highways that bypassed the slow surface streets. The entire geography of American life was redrawn around the exit ramp. What was lost was harder to see, but it was real.

The small-town, slow-paced, local character of American road travel was mostly extinguished. The experience of actually passing through the places you were traveling between, instead of flying past them at freeway speed, became a specialty item that road trip enthusiasts had to deliberately seek out. The weird, improvisational, do-it-yourself culture of the early auto trails, where a trip across the country was a serious adventure, was replaced by a smoother, faster, blander version that treated the land in between as something to be endured rather than experienced. The interstates made the country more efficient, more connected, and in some ways, much duller.

All of that pre-Interstate history, from Horatio Jackson’s bulldog Bud to Carl Fisher’s Lincoln Highway, to Eisenhower’s convoy in the Nebraska mud, to the Pennsylvania Turnpike’s midnight opening in 1940, happened in the span of a single human lifetime. A person born in 1900 would have grown up in a world where crossing the country by automobile was essentially impossible. By the time that same person was in their fifties, they could get on a four-lane divided highway and drive from New York to Chicago in a single day. By the time they were in their eighties, they could drive from coast to coast in less than a week.

The transformation was so fast and so total that most Americans barely noticed it happening. We tend to think of the Interstate System as something that has always been there, like the Mississippi River or the Rocky Mountains. It hasn’t. It is one of the most recent and most dramatic transformations in the history of the country.

And the people who made it happen, from the tire magnates and the eccentric Vermont doctors to the Oklahoma highway commissioners and the army lieutenants, deserve to be remembered.