You may be a car enthusiast who enjoys the blissful experience of driving, or simply someone who enjoys spending time behind the wheel watching the white lines flash by. Almost every driver knows that feeling of being on the open highway: that moment when the world narrows into the road ahead and the journey itself becomes the place you want to be. And it’s not just a matter of romanticizing old-fashioned driving. It turns out that young people actually enjoy driving just as much as older generations. The US was practically built on that feeling. From the first unpaved cart paths to the smooth asphalt of modern highways, our highways are more than just infrastructure. They are a legacy of freedom.
With over 27,000 miles of asphalt arterial roads, the American Interstate Highway System is one of the largest highway networks in the world. It literally moves the economy by connecting cities, small towns and coastlines, while also serving as a national defense asset. Before their creation, America’s highways were a patchwork of rugged, disconnected routes. That changed in 1956, when President Dwight D. Eisenhower signed the Federal-Aid Highway Act, inspired by his grueling 1919 cross-country convoy and after seeing the efficiency of Germany’s Autobahn system. The result was a standardized high-speed highway system that redefines the way America drives, acts and mobilizes.
And that makes the eldest special. They were built before America had borders on a map or uniform road signs. Some still cling to their original alignment, which winds through both the countryside and the cities. Here are five of the oldest highways in the US that still help people pursue the American Dream.
The Boston Post Road – US Route 1
The Boston Post Road returns here because not only is it one of the oldest roads in the US, it is America’s first highway, the foundation for everything that followed. The Boston Post Road was America’s first true mail route, a colonial network that connected Boston to New York City in 1673. Built atop Native American trails that predated European settlement, it became the backbone of early communication and trade. By the 18th century, postal workers carried letters, including the Boston News-Letter, the nation’s first newspaper, along the bumpy paths. In 1753, Benjamin Franklin, then deputy postmaster, crossed the road himself and installed milestones to standardize postal rates. In 1783, it was America’s first long-distance stagecoach service, transforming from a modest courier route into a full-fledged highway that was faster, safer and vital to a growing country.
Today, the bones of that 17th-century route still live beneath the modern American highway system. When America began numbering its roads in the 1920s, two major stretches of the Boston Post Road were reborn as U.S. Route 1 and U.S. Route 20, while other stretches still exist as U.S. Routes 5, 16, and 44. The Upper, Lower, and Middle Post Roads that were once colonial dirt roads have now become some of New England’s busiest thoroughfares, carrying commuters, freight, and weekend tourists along the same path that once carried mail on horseback.
The national road – American route 40
If you want to go back to the beginning of America’s love affair with highways, start with the National Road – the nation’s first federal highway project. Construction began in 1811 in Cumberland, Maryland, and by the mid-1800s the road extended all the way to Vandalia, Illinois. People used it as a path to the border in the west. Wagon trains and stagecoaches passed through, as did some of the very first automobile owners, all heading west over the stone and sand surfaces.
The National Road has had several names over the years, including the Cumberland Road, the National Pike, and more. As the western border began to grow, it became the main crossroads for all trade and settlement in the area. Shops and taverns appeared next to it and it wasn’t long before it was nicknamed “America’s Main Street.” By the time 1912 arrived, the route had been incorporated into the National Old Trails Road, virtually reviving it with the automobile boom of the 1920s. As cars began to replace the wagons, the feds began pouring significant money into improving the rough stone surface of the road with smooth asphalt.
In 1926, what was left of the old National Road was officially incorporated into U.S. Route 40, a road that began in Atlantic City, New Jersey and extended all the way to San Francisco, California. Even two hundred years later, it may not be the most expensive highway to drive on, but the National Road is still there and its old stones are a reminder that the country’s history continues to stretch on for miles.
The Lincoln Highway – US Route 30
Carl G Fisher was a car enthusiast and entrepreneur with a dream. He wanted to see the day when Americans could take to the open road and travel on their own terms. There was a problem with that vision, however: Less than half of his proposed 3,000-mile route used roads that already existed, so engineers had to create large stretches from scratch. The result included some pretty fancy infrastructure: 40-foot-wide, 12-inch-thick concrete slabs with sloping curves and guardrails designed to keep cars hurtling along at a thrilling 35 mph. Thus the Lincoln Highway was born, and pieces of older roads like the Lancaster Turnpike, Conestoga Road, and the Mormon Trail were stitched together to create the first true transcontinental highway designed from the ground up for cars.
When it opened, the slogan “See America First” became a bit of a rallying cry. It wasn’t long before gas stations, motor courts and roadside restaurants sprang up to cater to the new road trippers, and suddenly traveling became an adventure in itself. The Lincoln Highway was finally completed in 1925, the same year that marked the end of the era of said roads. The new numbered highway system turned much of the old Lincoln Highway into US Route 30.
In 1928, concrete markers with a large “L” were placed almost every mile along the route. However, not many of those markings have survived. In 2000, Pennsylvania’s Lincoln Highway Heritage Corridor revived the spirit by putting up 150 new markers, which still serve as a reminder that this was the place where the great American road trip was born.
The Dixie Highway – US Route 25, 41 and others
In 1915, the Dixie Highway began as a large, complicated network that ran from Chicago all the way to Miami. The whole idea was to connect the rugged north with the sun-drenched south. Carl G. Fisher, the same man who invented the Lincoln Highway, got things going, and a wave of new drivers jumped at the chance to trade train rides for the freedom of their own cars. Local governments and community groups took on the work in their own backyards, turning the highway into a patchwork: some sections consisted of smooth pavement, while others were just dirt roads linked together under the name Dixie Highway.
The Dixie Highway became Florida’s main artery for early tourism. Snowbirds flocked south, produce moved north, and roadside towns came alive with gas stations, motels and quirky roadside stops hoping to catch the attention of passing motorists. By the late 1920s, the Dixie Highway faded into the background as the new American highway system took over. Today, US 41, US 25, and US 1, among others, make up what remains of the Dixie.
Many abandoned highways are collapsing under modern infrastructure. However, if you drive through Georgia, Tennessee or Florida, you will see parts of the old road. They are narrow, two-lane stretches that feel like a time warp, full of dust, sunshine and the unmistakable smell of engines warming under the southern sky.
The Pacific Coast Highway – California State Route 1
California’s Pacific Coast Highway, or as most like to call it, PCH, doesn’t have centuries of history attached to it, but it has a spirit that feels endless. The road came together in 1934, composed of old coastal routes between Orange and Mendocino counties, and became the most scenic route in the country. Building it was no easy feat. During the Depression, crews blasted through cliffs, weaved through canyons and built bridges like the Bixby Rainbow Bridge, which still stands proudly in Big Sur.
The PCH stretches nearly 700 miles, running from south to north across the state, winding through places like Los Angeles and San Francisco—even crossing the Golden Gate Bridge. If you throw in US Route 101, you get a virtually uninterrupted path along the entire Pacific coastline.
The first section of the highway ran between Ventura and Santa Barbara, where wooden causeways used to carry cars above the swampy lowlands. But the real showstopper is the stretch between Big Sur, Carmel and San Simeon, where Hearst Castle is located. It took engineers 18 years to excavate the 75-mile stretch, with 33 bridges clinging to cliffs and winding around mountains. Of course there are landslides and blood-curdling turns, but that doesn’t stop adventurous drivers. Unlike the nation’s busiest highways, the PCH is still one of the best road trips you can take in America. It’s a reminder that the ride itself can be just as good as anywhere you go.
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