Just like you, dear reader, we at Jalopnik live for the love of cars, motorcycles and airplanes. The race tracks, the roar of multi-cylinder machines, the speed and the smell of burnt clutches and melting rubber are more stimulating than a double espresso. Okay, maybe not espresso, we love that stuff, but you get the idea, right? Heck, we even have a bucket list of roads we’d like to drive. With this passion comes the love of speed, and that speed turns the landscape into a blur and bends time between turns. Some of us prefer to take our foot off the gas and trade the track for a quiet back road, finding joy in the journey itself.
This one is for the love of open roads and, most specifically, some of the oldest American arterial roads still in use. These are trails that once carried Native Americans, mail riders, settlers, stagecoaches and later automobiles. But America’s highway system was carved out, debated, and paved a mile at a time until it became the vast network we drive today. Muddy wagon paths eventually became the blueprint for modern roads, and each era added its own layer of history. The U.S. highway system now handles nearly 8 billion vehicle miles per day.
Some of the oldest roads have been widened, paved, diverted and renamed. Running through bustling cities and sleepy suburbs, they quietly remind us that the foundations of American travel were laid centuries ago. Here’s a sneak peek at some of the oldest roads in America that are still open to daily traffic, and each is a living time capsule for modern wheels.
Old Mine Road
It is believed that Old Mine Road was built first by Native Americans and then by Dutch settlers in the 17th century. It is one of the oldest commercial routes in North America. This is a 100-mile route that runs from Pahaquarry, New Jersey, to Kingston, New York. What started as a colonial ore transport trail now runs through the Delaware Water Gap National Recreation Area. In New Jersey, it still retains its pre-Revolutionary charm, with overgrown shoulders, sagging barns and the occasional colonial relic hiding in the woods.
The road has seen its share of drama. A doomed plan to build the Tocks Island Dam in the 1970s left nearby towns empty, forcing 4,000 families to move under the federal government’s relocation program. The dam was never built, but the ghosts persist, and entire communities have been displaced because of a reservoir that was never filled. Today, the National Park Service keeps the corridor undeveloped, allowing the forest to reclaim what industry has abandoned.
There are many ultimate summer road trips we’d love to take around the world, but here at home there are hidden gems like the Old Mine Road. Driving the Old Mine Road feels like leafing through the oldest chapters of American travel. The surface shifts from smooth asphalt to gravel and is littered with craters, so you’ll need something bigger than a Miata to survive the potholes. For those willing to crawl through the bends, the reward is silence, solitude and a history that predates the car’s horsepower.
King’s Highway-Boston Post Road
The King’s Highway was commissioned by King Charles II in the 1650s and completed around 1735. This was America’s first highway, stretching nearly 1,300 miles from Charleston, South Carolina, to Boston, Massachusetts. The section between Boston and New York opened in 1673 and also served as the colonies’ first postal highway, earning it the name Boston Post Road. It’s fitting that the King’s Highway, and specifically the Boston Post Road, is considered the oldest stretch of road in the United States.
The Boston Post Road wound through the mountains of Western Massachusetts, skirting the shores of Long Island Sound and cutting through the green expanse of the Connecticut River Valley. What started as dirt and hoof prints eventually evolved into the modern highway spine of the Northeast. Although the dirt roads have been replaced with smoother pavement, the route still encompasses the same landscape that Native Americans and early settlers once traversed centuries ago.
The Upper Post Road ran from New Haven through Hartford and Springfield to Boston and was lined with taverns for weary travelers. The Lower Post Road, now US Route 1, ran along the coast through Providence before turning toward Boston. Today, the Middle Post Road is followed by Routes 16 and 109; this was the shortest section, and once the most dangerous, thanks to King Philip’s War.
Old Albany Post Road
Officially established in 1669, the Albany Post Road followed Native American trails once used by the Wappinger and Wicopee tribes, connecting what was then New Amsterdam (New York) to Albany. In 1703, under the reign of Queen Anne, the British turned it into a ‘public highway’, naming it the Queen’s Road, a fitting royal title for a route that still refuses to be tamed.
This winding 6-mile stretch in Philipstown, New York, is over 350 years old and has never been paved. It is the oldest road in New York and the second oldest road in the United States, after the Boston Post Road. This particular section of historical significance is called the Old Albany Post Road and has seen everything from George Washington’s troops to Benjamin Franklin’s landmarks, which still stand on the tree-covered roadsides today.
The locals consider it sacred ground. The Old Road Society of Philipstown, New York, an all-volunteer group founded in 1982, has fought to preserve the dirt road for decades, fighting every well-meaning official with a bucket of asphalt. Their mission is clearly to keep the past intact, potholes and all. Most of the original Albany Post Road has been incorporated into modern roadways, but this 6-mile dirt section remains and was recognized and added to the National Register of Historic Places in 1982.
Mohegan Road-Connecticut Route 32
Long before Connecticut had freeways and traffic jams, there was Mohegan Road. First constructed in 1670 between New London and Norwich, Connecticut along the east bank of the Thames River, it was previously a well-trodden Indian trail used for more than a century. The settlers simply widened it, gave it a name, and turned it into one of New England’s first true highways.
In 1792, Mohegan Road rose to become New England’s first turnpike, and only the second turnpike in the entire United States. Travelers rolled their wagons over the tracks and the route became a commercial lifeline for Connecticut’s growing towns. When the era of numbered highways dawned, the road was merged into the New England Interstate system, reborn as Route 32 in 1922.
Today, Route 32 still follows much of that original colonial route, winding through the forests and small towns of eastern Connecticut, from the coast of New London to the hills of Willimantic. It is difficult to imagine that this modern two-lane route once carried ox carts and mail riders. Three centuries later, it’s still doing what it was built to do: connecting people, commerce and a piece of New England’s oldest road history. Sometimes driving the back roads is more satisfying than flying down the highway, and when those roads hold a bit of history, it’s just the icing on the cake of a perfect drive.
Farm Highway – Connecticut Route 108
Before it was simply a numbered connector in southern Connecticut, Route 108 had one of the longest pedigrees in the state. The story begins in 1696, when the Farm Highway, today’s Nichols Avenue portion of Route 108, became Trumbull’s first highway. Built to connect farms and settlements between Norwalk and New Haven, it is considered Connecticut’s third-oldest documented highway, behind only the Mohegan and Boston Post Roads.
Two centuries later, into the 1920s, the number 108 didn’t even belong to Trumbull. At the time, State Highway 108 ran along the New State Road and Tolland Turnpike between US 6 and Route 83 in Manchester before continuing north into Massachusetts. The modern Route 108 as we know it didn’t go into service until January 1, 1932 and didn’t get much love at first. The road ran just 5.45 miles from a cul-de-sac in the village of Huntington to Perry and White Streets in Shelton, with no real connections to other state routes – it was basically a lonely local shortcut with a fancy track.
Things slowly improved. A 1951 bill pushed for an extension from Shelton to Penny Avenue in Trumbull, followed by an extension south in 1952. It briefly disappeared from the maps in 1957, but did not appear until 1960. In 1963, Route 108 finally earned its respect when an additional 3 miles were added from Route 8 to US 1 via Nichols Avenue, upgrading it from a forgotten farm road to a legitimate thoroughfare.
Three centuries later, Route 108 remains proof that some roads survive history, and while it may not be one of the best places you’d want to take your car, it’s still an essential part of America’s road network past.
#oldest #roads #Jalopnik


