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My Top 10 Insights From Traveling Route 66

When I was a child growing up in Chicago, I learned of the great "Mother Road" that takes you from Grant Park to the Santa Monica Pier -- and it was my dream to drive all of its 2,448 miles.
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It's great to be back in San Francisco, after a three-week vacation -- where I flew to Chicago, and then drove all the way back to California via Historic Route 66. When I was a child growing up in Chicago, I learned of the great "Mother Road" that takes you from Grant Park to the Santa Monica Pier -- and it was my dream to drive all of its 2,448 miles. It's the road that Okies took during the Great Depression to find jobs in California, and in the 1950s and '60s it came to symbolize America's move west to the Sunbelt. And the fact that Route 66 no longer exists (the U.S. Highway System had the road de-commissioned in 1985, because the Interstate made it obsolete) made this trip feel like a real adventure. I blogged every day, and learned a lot of things along the way -- some profound, some of them just plain obvious. Here are my top 10 insights from driving Route 66, as we leave Chicago for Los Angeles.

(1) Illinois Does The Best Job Promoting Route 66
Before going on this trip, I spent a lot of time studying Route 66 -- cross-referencing books and online guides with Google Maps to follow it as faithfully as possible. But in Illinois, that work was largely unnecessary -- as the Land of Lincoln does a great job promoting Route 66.
Every town milks its connection to the Mother Road in the most ridiculous way -- from the Gemini Giant in Wilmington, to the old two-room jailhouse in Gardner.

South of Springfield, it gets tricky -- as there are two possible alignments. Take the one further west, as it follows a stretch of original 1920s roadside brick -- a charming part of Route 66 that I dubbed the "Red Brick Road." Driving it was surreal.

(2) St. Louis Reminded Me Of New Orleans
For better and for worse, Saint Louis has a lot in common with New Orleans -- an historic 18th Century city with French influence, that has fallen on hard times. All the guidebooks told me to avoid driving in much of St. Louis, but I ignored it -- and witnessed the worst inner-city poverty I have ever seen. I was lucky to stay in the Soulard, a charming red-brick neighborhood south of Downtown with cobblestone streets. The word soulard is French for "drunk," and each year Soulard throws the biggest Mardi Gras celebration outside of New Orleans.

(3) Missouri's Poverty Was Overwhelming
I had never been to Missouri, but the state's poverty as you drive through the Ozarks was truly depressing. Trailer homes line all of Route 66, with churches like Assembly of God & Seventh Day Adventists -- along with the occasional cheap porno magazine shops. There were few of the touristy Route 66 stops we saw in Illinois (except for the World's Largest Rocking Chair, just west of Cuba.)
When I stopped for lunch in Springfield, I mentioned to the waiter how struck I was at the level of poverty in Missouri. "We got all kinds," he replied to me. "We've got the trash and the filthy rich." But I never saw the filthy rich.

(4) What's The Matter With Oklahoma?
In 2004, journalist Tom Frank wrote his bestseller What's the Matter with Kansas? -- but the question should really be asked about Oklahoma. It is the only state where Barack Obama failed to win a single county, and of course in 2010 Republicans swept every statewide office. But Oklahoma's favorite son is political humorist Will Rogers -- and locals call Route 66 the Will Rogers Highway. I visited the Will Rogers Museum in Claremore, and bought a CD of his 1930's radio broadcasts. The guy was a hardcore economic lefty, and he had some choice words about what the white man did to Native Americans. My only guess of what went wrong is the prevalence of "pro-life" religious billboards along Route 66.

(5) Wind Energy From The Texas Panhandle
When speaking of alternative energy, Van Jones says we have a "Saudi Arabia of wind energy" in Middle America. Nowhere is that more true than the Texas Panhandle, which has hundreds of miles of flat countryside, and the harshest wind I've ever seen. It's ironic that Texas, which prides itself on vast oil fields and a "drill, baby, drill" mentality, actually could help relieve our dependence on fossil fuels and lead us into the 21st Century.

(6) Amarillo Has A Good Gay Scene
Here's a pop quiz: which city has more gay bars? Amarillo -- a city of 200,000 in the very, very Republican Texas Panhandle, or Albuquerque -- a city of 500,000 in the "leaning blue" state of New Mexico? The answer, surprisingly, is Amarillo -- with its vibrant venues like Sassy's (which has karaoke every Friday night until 12!) My theory is that if you're gay in the Texas Panhandle, there is really nowhere to go but Amarillo. But gay singles don't really mingle in Albuquerque. New Mexico is where middle-aged same-sex couples settle down and look at the stars.

(7) There Are Two Types Of Cowboy Hats:
Okay, this one's a bit obvious -- but it was news for a city boy like me from San Francisco. As anyone who saw my photos on Facebook, I morphed into quite a cowboy on this trip -- and learned that every cowboy has at least two hats: a dark felt hat to keep them warm in the cool months, and a white straw hat to keep cool during the summer. And according to the clerk at Cavender's in Amarillo (where I bought my Stetson), you shouldn't wear your straw hat until Easter.

(8) New Mexicans Are Sweet, Laid Back And Friendly
Besides being the most beautiful state on Route 66, the Land of Enchantment truly has what other parts of the country call Southern Hospitality. Everything closes on Sundays -- but when the waiter in Las Vegas, New Mexico heard that I wanted a bolo tie, he called the local jeweler at home and asked him to open up his shop so I could buy one. In Santa Fe, the parking lot attendant let me stay there for free -- if I promised I'd leave before 10:00 p.m. And the bartender gave me a free coffee rather than use my debit card, because I'd been driving across the country. That's what New Mexico culture is about.

(9) Private Cars Should Be Banned From The Grand Canyon
I did a side trip to the Grand Canyon, which was lovely -- but I didn't have time to hike all the way to the bottom, and the South Rim with its traffic woes felt like a big amusement park (and I wasn't there during peak season). There's been talk of banning private cars from the Grand Canyon, which would mean that most visitors would arrive by train from Williams, Arizona. Which is a brilliant idea. Williams was the last Route 66 town to be by-passed by the Interstate, and the only thing that's kept it from turning into another McLean, Texas is its proximity to the Grand Canyon. An exclusive gateway for travelers would be a big economic boon to Williams, Arizona.

(10) Don't Miss The Black Mountains Of Western Arizona
The last 160 miles of Route 66 in Arizona deviate from the Interstate quite a bit -- going through towns like Seligman, Kingman and Oatman and a beautiful stretch of open desert. Oatman is cute with its wild burros roaming the streets, but it seems like all 150 of its residents work in the touristy gift shops. The real reason to travel this part of Route 66 is the curvy roads in the Black Mountains. As you maneuver sharp turns at 15 miles/hour, imagine what the Joad family in the Grapes of Wrath went through -- with all their belongings in an old clunker. This is the last stretch of road before entering the Promised Land of California, and is by far the most treacherous -- but it's also the most rewarding.

Of course, this top 10 list didn't even make it to California -- so here's a bonus insight.

(11) Santa Monica Is Cool -- But Venice Is Cooler:
For its last few miles in Los Angeles, Route 66 follows Sunset Boulevard -- and then Santa Monica Boulevard all the way to the Pacific Ocean, where it ends at Santa Monica Pier. I've always been a fan of Santa Monica, but I spent the next day in Venice -- canvassing for Debra Bowen's campaign for Congress. Venice offers everything that Santa Monica provides -- progressive politics, walkable neighborhoods and a nice ocean breeze -- but it's far less gentrified and has more of a hippie vibe. It reminded me a lot of Berkeley (where I lived for eight formative years); in many ways I felt right at home.

After a couple days in L.A., I drove up to San Francisco -- but with Highway One's road closures due to mudslides this winter, I had to hop onto US-101 for most of the time. It's a road that most Californians are familiar with, so I'll refrain from any commentary ...