Classic American Road Trips — and One That Is Turning 100
- kaceyrose9
- 5 days ago
- 4 min read
Who doesn't love a summer road trip?
Route 66 turns 100 this year. Established November 11, 1926, the Mother Road stretches from Chicago to Santa Monica across eight states and nearly 4,000 kilometers of American mythology. John Steinbeck called it "the mother road, the road of flight" in The Grapes of Wrath. The Okies drove it west during the Dust Bowl, chasing a California that didn't always deliver what it promised. Later it became the road of postwar optimism — diners, drive-ins, neon signs, the American open road as dream rather than necessity. The centennial is being celebrated all year long with events, festivals, and car shows from Illinois to California. You don't have to drive the whole thing to feel its pull. Even a stretch of it, through the red rock country of New Mexico or the high desert of Arizona, is enough to understand why it captured the American, and foreign, imagination for a century.
But Route 66 is just the beginning. America has roads that most people have never heard of that are as beautiful as anything in the world. Here are six classic American road trips that I've taken myself and would send anyone on.
Highway 50 — The Loneliest Road in America
Life Magazine called it the loneliest road in America in 1986 and actively discouraged drivers from taking it. That warning became the best advertisement it ever received.
Highway 50 crosses Nevada from east to west through ghost towns, ancient lake beds, and mountain ranges with limited services for hundreds of miles. The ghost towns aren't metaphorical. Places like Austin and Eureka boomed with silver mining in the 1860s and then emptied almost as fast as they filled. The landscape they left behind is the American West before anyone arrived to tame it. Plan for a multiday trip if you want to truly experience it, and make sure to stop at Great Basin National Park for some of the darkest skies and best stargazing in the continental United States. Details at travelnevada.com/road-trips/loneliest-road-in-america.
The Turquoise Trail National Scenic Byway — New Mexico
Most people drive the interstate between Albuquerque and Santa Fe without realizing there is an older, stranger, more beautiful road running parallel to it.
The Turquoise Trail winds through old mining towns — Madrid, Cerrillos, Tijeras — that feel suspended in another century. Cerrillos was a turquoise mining center for indigenous peoples long before the Spanish arrived, and the Spanish arrived in the 1500s. Madrid was a coal mining town that went bust in the 1950s and was reborn as an artists' colony in the 1970s. Today it's galleries, studios, and one of the best roadhouses in New Mexico. About an hour of driving that feels like an entirely different world. turquoisetrail.org is worth reading before you go.
Beartooth Highway — Montana and Wyoming
Considered by many the most beautiful road in America, and I would not argue with them.
The highway climbs to nearly 11,000 feet through the Beartooth Mountains above Yellowstone, past alpine lakes, glaciated peaks, and tundra that feels more Scandinavian than American. It was built in the 1930s as a New Deal project, carved into some of the oldest exposed rock on earth — granite and gneiss dating back nearly four billion years. Charles Kuralt once called it the most beautiful drive in America, and he drove a lot of roads. It's only open in summer and closes early when the weather turns. Start in Red Lodge, Montana — a former coal mining town with a genuinely good main street — and drive west toward Cooke City. Pull over constantly.
The Overseas Highway — Florida Keys
113 miles of driving over water from Miami to Key West across 42 bridges, the Atlantic on one side and the Gulf of Mexico on the other. The Keys were connected to the mainland by Henry Flagler's Overseas Railroad in 1912, an engineering feat so audacious it was called the Eighth Wonder of the World. The Labor Day Hurricane of 1935 destroyed the railroad, and the highway was built on what remained of the old rail bridges. You're driving on history. Stop at Bahia Honda State Park for one of the best beaches in Florida, or make an earlier stop in Islamorada, the sportfishing capital of the world and considerably quieter than Key West. Arrive in Key West at dusk. The sunset ritual at Mallory Square is worth it.
Going-to-the-Sun Road — Glacier National Park, Montana
50 miles through Glacier National Park over the Continental Divide, open only in the summer months. The road was carved into the mountainside through the 1920s and 1930s, completed in 1932 by workers using hand tools on sheer cliff faces. The Blackfeet Nation has lived in and around these mountains since long before any road was built. The park sits on land ceded under a treaty that many consider deeply unjust, a history worth knowing as you drive through one of the most beautiful landscapes on the continent. The glaciers that gave the park its name are disappearing. Some scientists estimate they could be gone within decades, which gives the whole experience a particular weight.
One More Worth Mentioning — The Cascade Loop, Washington State
400 miles through the North Cascades, apple orchards, wine country, and old mining towns that most Americans have never heard of. The North Cascades are among the most glaciated mountains in the contiguous United States, home to more glaciers than any other range outside Alaska. The Indigenous peoples of this region — the Wenatchi, the Methow, the Sauk-Suiattle — have fished its rivers and crossed its passes for thousands of years. Plan this as a multiday trip with stops and hiking, and get your permits in advance. cascadeloop.com has excellent suggestions for pacing and planning.
America is extraordinary when seen from the road. These are six trips to start. Add yours in the comments — I'm always collecting recommendations.
Planning a road trip or need help with where to stay along the way? That's exactly what I'm here for.
HAPPY FLAG DAY!
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