The Loneliest Road – San Francisco to the Chesapeake Bay, 3,200 miles

Running coast-to-coast through the heart of America from sea to shining sea, US-50 passes through a dozen different states and four state capitals, as well as the nation’s capital, Washington, D.C. Along the route are some of the country’s most magnificent landscapes: the Sierra Nevada and the Appalachian and Rocky Mountains, the endless farmlands of the Great Plains, and the desiccated deserts of Utah and Nevada. It follows the footsteps of pioneers, and gives a reverse time line of national development. Heading west to east, you can travel back in history from the cutting-edge high tech of contemporary Silicon Valley, across the Wild West frontier of the mid-1800s, and through lands the likes of Daniel Boone and countless others pioneered in the 1700s, before arriving at the Atlantic Ocean near some of the oldest and best-preserved colonial-era landscapes in the United States

All the way across the country, US-50 passes through literally hundreds of timeworn small towns, the great majority of which have survived despite the modern onslaught of Wal-Marts and fast-food franchises. Blue Highways author William Least Heat-Moon writes about US-50, “for the unhurried, this little-known highway is the best national road across the middle of the United States.” The route offers such a compelling cross-section of the nation that Time magazine devoted nearly an entire issue (July 7, 1997) to telling the story of the road it called the ‘Backbone of America’

From its start at San Francisco, the route cuts across California’s midsection, passing the state capital at Sacramento before following the route of the old Pony Express up into the Sierra Nevada to the shores of Lake Tahoe and into Nevada. The Nevada portion of the route, dubbed ‘The Loneliest Road in America’ by travel writers and tourist boards, is one of the most compelling long-distance drives in the country—provided you find miles and miles of little more than mountains, sagebrush, and blue sky compelling. The Great Basin desert continues across half of Utah, but then the route climbs over the Wasatch Front and onto the national park–packed red-rock country of the Colorado Plateau

Continuing east, you cross the Continental Divide atop the Rockies, then follow the Arkansas River along the historic Santa Fe Trail. For fans of vanishing Americana, the route really comes into its own here across the Great Plains, with its hypnotically repetitive landscape of water towers, windmills, railroad tracks, and one small town after another

After bisecting Missouri from Kansas City to St. Louis, US-50 crosses the Mississippi River into a much older and more settled landscape, through the agricultural heartlands of Illinois, Indiana, and Ohio. After climbing into the Appalachian backwoods of West Virginia, US-50 emerges suddenly into the wealth and power of downtown Washington, D.C., before passing through the still perfectly picturesque fishing and farming communities of Maryland’s Eastern Shore. Plan your journey here

The Road to Nowhere – Westhope, North Dakota to Brownsville, Texas, 1834 miles

Once the only entirely paved route from Canada to Mexico (as hard-to-find postcards along the route still say), US-83 is still the shortest—from Westhope, North Dakota, dead south to Brownsville, Texas, and beyond to Matamoros, Mexico, seemingly without turning once. Its grim nickname, ‘The Road to Nowhere’, is alternately unfair and then not severe enough, for the route navigates some of the widest and most aesthetically challenged landscapes in the country: the yawn-inducing rolling grasslands of the northern Great Plains, the beefy expanses of western Nebraska and Kansas, and the mesmerizing heat of the Texas/Oklahoma Panhandle, before following the lower Rio Grande south to the Gulf of Mexico. Yet on US-83 you’ll also take in some phenomenal country: verdant farmland dotted with really small towns, endlessly shifting prairie grassland, winding Missouri River roadways, and plain, isolated, where-the-hell-am-I agricultural expanses

Following roughly along the 100th Meridian, US-83 marks the historic divide between the ‘civilized’ eastern United States and the arid western deserts. Physiography aside, this route’s cultural landscape centres around small but self-sufficient farm or cattle communities that date back to the last days of the Wild West and that are far enough off the tourist trail to retain an unselfconscious, aw-shucks quaintness. For endless miles in every direction, telephone and power poles provide some of the only signs of life between the highway and the distant horizon, though the towns—where average speeds drop suddenly from 70 mph to radar-enforced 25 mph or slower—are spaced just often enough along the highway to serve your food-and-fuel needs

Best of all, US-83 manages to trans navigate this broad, odd nation, albeit north-to-south, without once grazing a conventional tourist attraction. Here in the nation’s heartland, conversations over a daybreak breakfast, afternoons spent cooling off by municipal swimming pools, and twilight American Legion baseball games provide the stuff of truly memorable Road Trip diversions, and for that reason alone, US-83 remains a must-do long-distance byway. Plan your journey here