I reach the Mother Road on a full tank of high expectations. No more uncertain turns, no more Google (bike) Maps mishaps. I’ll cruise this legendary route all the way to sunny California. Praised by musicians and the media, Route 66 will show me a fossilized look at bygone American culture I never grew up with. I’m excited to explore my own country on a famous road that — bonus — is now popular among bicyclists. Maybe I’ll make friends!

Adventure Cycling’s christening it Bicycle Route 66 pads my confidence. Directional signs and wide shoulders all the way to the ocean, right? Actually, quite the contrary. America’s Main Street immediately disappoints with decaying pavement and dangerous conditions, like a disappearing shoulder. Learning about the road’s historical importance is the only thing that saves my experience from total disappointment.

I start the morning in Clinton, Oklahoma at a Route 66 Museum. Historical perspective helps me appreciate Route 66 during the golden age of automobiles when small towns thrived on cross-continental traffic.

Growing up on the East Coast and after the highway was decommissioned, I couldn’t even have told you where Route 66 started and ended — it was just somewhere out there and not close to New York. Time for me to get educated! Clinton is the first of three Route 66 Museums. I’ll also stop in Elk City, OK and Kingman, AZ. Here’s a summary of what I learned.

Route 66 History
Reliable long distance roads have been a priority since the Jefferson Administration when the National Road was chartered in 1806 to link the Ohio River with the Atlantic Ocean. Remember the day I spent on the National Road back in West Virginia and Ohio? While maybe historic, it sucks for bicycles. The National Road reached central Illinois before it made more sense to forge west with railroads, which were making greater progress than roadways.

America’s dependence on roads didn’t diminish, and in 1893 the National Good Roads Association formed to promote construction of roads to get commerce and crops to markets and mouths more efficiently. A federal highway act passed in 1921 matched state expenditures to build highways with federal dollars 50-50. This led to a web of trails and highways, but they weren’t well organized across state lines.

America still lacked an all-weather road linking the Midwest and West Coast. Enter Route 66 a.k.a. the Mother Road, which fused 18 older highways into one continuous stretch.

After initial confusion, I realize that Route 66 is not just one path, but several depending on the alignment that shifted over the years. The road was like a winding river, changing course here and there, sometimes just a block north or south. Businesses boomed and failed accordingly.

What never changed was its origin in Grant Park, Chicago and finish in Santa Monica, California. In between stretches some 2,448 miles that symbolized the gasoline-fueled Great American Road Trip.

Commissioned on November 11, 1926, Route 66 earned nicknames such as The Mother Road, America’s Main Street, America’s Highway and Will Rogers Highway. The road inspired Bobby Troupe’s song “Get Your Kicks on Route 66” (more famously sung by Nat King Cole) and was featured in John Steinbeck’s Grapes of Wrath about Depression era Dust Bowl farmers who hit the road to California in search of better weather and jobs along what Steinbeck called “the road of flight.”

At the museum in Kingman, Arizona I stop and stare at black and white pictures of desperate families on early automobiles with sad bug-eye headlights. Chairs, chicken wire and children are piled high. The kids are dirty, in tattered clothing and rail thin. Heading west hoping for a better future, they probably didn’t find it, or their car broke down before they got there. Maybe they should have invested in a Travoy trailer. Suddenly I feel pretty fortunate to be digesting a frozen root beer and those heavenly pulled pork “redneck” nachos from Redneck’s Southern Pit BBQ (you’ll just have to wait until we get to Arizona for tasty details).

By 1937 the route was fully paved, allowing cars to go faster. The unintended consequence was more deadly accidents. States formed highway patrols to impose order. Engineering professors from Oklahoma State University developed the parking meter to encourage turnover in towns inundated with automobiles.

After WWII, railroads were unable to keep up with demand for interstate commerce. Truck traffic capitalized on Route 66 to reach consumers more efficiently and at lower costs. Quirky roadside attractions sprouted up to complement gas stations, motels and restaurants. The good times were rolling, but not fast enough.

A network of roads was needed with higher speeds and fewer access points. The Eisenhower Administration developed an interstate system without stop signs or small towns to slow down traffic. Route 66 went from model continental thoroughfare to outdated alleyway.

When in 1984 Interstate 40 bypassed the final Route 66 town of Williams, Arizona, the Mother Road was forced into retirement. A year later it was stripped of signage and decommissioned. Ever since then it has fallen into disuse despite a loyal group of revivalists and curious foreign tourists wondering what the real America is like in between our overdeveloped coastlines.

You don’t hear Americans clamoring to take a Route 66 road trip nowadays, but foreign fascination is for real. There are Route 66 driving clubs abroad. Vestiges of America's Main Street attract enthusiastic visitors from Europe, China, Australia and New Zealand. In Seligman, Arizona I spoke with a shop owner who said during the summer about 20 full-sized tour buses disgorge passengers here each day. You wouldn’t believe the tacky souvenirs that sell just because Route 66 is stamped on them. America, amen.

I guess Route 66 taps into the desire for an authentic driving experience that combines freedom and exploration with the turn of a steering wheel. It’s the same illusion automotive advertising employs to sell us the latest model vehicle in postcard-perfect settings like Monument Valley, a snowy mountain pass or other unrealistic backdrop where we’ll never ever drive. Reality-based car commercials circling around big box store parking lots must not have the same appeal.

Along Route 66 I meet tourists with charming foreign accents and wonder what the heck they’re doing in McLean, Texas or Ash Fork, Arizona where I would never stop were I not stuck moving like molasses on this bicycle.

Maybe it’s more fun in a car. Crumbling road conditions make Route 66 feel more like Route 666 on a bicycle. In the end I soften up on the old Mother Road because she captures the spirit of small town America, what’s left of it anyway. It’s also where I meet a very unlikely cyclist, and her bold story is next.