**đźš—Road Trip, the call of a generation
A Cross‑Country Daydream from Route 66 to Route 20**
America’s Love Affair With the Open Road
With gas prices climbing and no relief in sight, it’s fair to wonder whether the classic American road trip is slowly becoming an endangered species. Then again, air travel isn’t exactly a walk in the park these days either.
Still, before we declare the road trip obsolete, it’s worth pausing to appreciate the romance, freedom, and pure Americana that grew out of our national love affair with the automobile.
The Mother Road: Route 66
One iconic road immediately comes to mind — and I’m pleased to say I’ve explored a small slice of it.
Route 66, the legendary “Mother Road,” was established in 1926 and stretched 2,448 miles from Chicago to Santa Monica. It wound through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona, carrying generations of dreamers westward.
Though officially decommissioned, roughly 85% of the route is still drivable. Vintage neon signs, retro diners, quirky roadside attractions, and weathered motels still line the way, offering a nostalgic glimpse into a bygone era.
America’s Longest Road: Route 20
If Route 66 is the most famous, Route 20 is the heavyweight champion. At 3,365 miles, it’s the longest
road in the United States — and it starts right here in Boston.
A Route 20 adventure would take you through 12 states and across the entire country, ending in Newport, Oregon. Along the way, you could:
- Stroll the Boston Esplanade
- Visit the Basketball Hall of Fame in Springfield
- Wander the Finger Lakes of New York
- Detour to Niagara Falls
- Swing up to Lake Placid, home of the 1980 “Miracle on Ice”
Then it’s onward through Pennsylvania and into Ohio, where Cedar Point awaits with some of the best roller coasters in the nation. Once you catch your breath, Route 20 rolls into Indiana and the Indiana Dunes National Park.
Across the Heartland and Into Big Sky Country
In Illinois, Route 20 carries you straight through Chicago before crossing the Mississippi River into Iowa.
Then comes Wyoming — Big Sky Country at its finest. You’ll pass through Lost Springs, the least populated municipality in America, and you’re just a side trip away from Yellowstone. Keep an eye out for bison; they don’t yield.
Montana only gets about ten miles of Route 20, but it’s close enough to tempt you toward the famous Going‑to‑the‑Sun Road, a bucket‑list drive if ever there was one.
The Final Push to the Pacific
Idaho brings a breather in Boise before the home stretch. The last state is Oregon, but don’t be fooled — there are still 451 miles to go before you reach Newport and the Pacific Ocean.
Quite the road trip indeed.
And Then… Maybe the Overseas Highway?
Once I’ve conquered Route 20, maybe I’ll head south to Florida for the Overseas Highway — 113 miles and 42 bridges ending at the Southernmost Point in Key West. A completely different kind of road trip, but just as iconic.
So… Is the Road Trip Doomed?
Maybe gas prices will rise. Maybe travel will keep changing. But the American road trip isn’t just about miles or money — it’s about freedom, curiosity, and the irresistible pull of the horizon.
As long as there are roads to follow and stories to chase, I don’t think the great American road trip is going anywhere.