Hit The Road Jack!

Driving the length of Route 66 will introduce you to the many pleasures of life in the slow lane.

A blue whale beached on the banks of a stagnant pond. A spaceman the size of a three-story building. A dinosaur with a red-haired damsel dangling from its toothy jaws. No, I’m not hallucinating again, just recalling a few of the more colorful landmarks I discovered during a recent roadtrip on that world-famous stretch of pavement known as Route 66.

For more than 50 years, the 2,400-odd miles of this historic road ran unbroken from the shores of Lake Michigan in downtown Chicago to the Pacific Ocean in Los Angeles. Along the way it gave birth to the quintessentially American notion that piling the whole family into the car and heading for the horizon could actually be an adventure.

Fortunately for those of us who still believe there’s more to roadtripping than making time on the interstates that replaced it, choice sections of Route 66 and many of its treasures are still out there waiting to be experienced. I know because I teamed up with a couple of friends to drive the length of it on the highway’s 75th anniversary.

That cross-country ramble turned out to be an absolute blast and it’s something I’d recommend highly to anyone who understands the irresistible pull of the open road. But be forewarned: Like all worthwhile undertakings, finding and following what’s left of the original Route 66 can require healthy doses of both patience and perseverance.

Even with a virtual library of Route 66 guidebooks and a thick stack of AAA maps at our disposal, my friends and I still managed to get lost at least a couple of times a day. And while we found the guidebooks’ lack of clear-cut directions frustrating at times, in retrospect I look back at all of our missteps as just another part of the adventure.

Of course, I wouldn’t be telling you this tale if there wasn’t an extraordinary payoff. From the homey little roadside café in the middle of Texas that served what still stands out as the best breakfast I’ve ever eaten to the spectacular sunset and the scent of rain-washed sage we enjoyed on a deserted stretch of two-lane west of Albuquerque, our trip convinced me that the rewards of seeking out the last remaining stretches of Route 66 are both countless and profound.

You see, when you stumble upon a long-forgotten stretch of the old road or one of its classic roadside attractions it’s like being let in on a juicy little secret. A secret made more appealing by the knowledge that all those bored-to-tears travelers whizzing by on the interstate a few miles away have absolutely no idea how much really cool stuff they’re missing.

Xtrordinary Xtra
All 2,400-odd miles of Route 66 weren’t paved until 1937. The last section of the old road—through Williams, AZ—was officially decommissioned in 1985.

Xtrordinary Xtra
If you’ve ever traveled cross-country you may have already driven on sections of Route 66 without knowing it. Many sections of Interstates 10, 15, 40, and 44 were laid down right on top of the old road.

The Facts
Name: Route 66
Location: Runs through eight states (Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California) and three time zones on its way from the intersection of Adams Street and Michigan Avenue in downtown Chicago to the foot of the Santa Monica Pier in Los Angeles.

My Advice

  • Here’s my number one rule: Leave your trip planning a little loose because, frankly, that’s where the magic is. Traveling unencumbered by prearranged hotel reservations gives you the freedom to explore an interesting bit of roadside kitsch you might be tempted to pass by if you’re feeling pressed to make another 150 miles before nightfall.
  • I’d also strongly encourage you to avoid eating at any national chain restaurants along the way. Discovering all the great one-off eateries that continue to keep the locals happy even after the interstates passed them by was one of the highlights of our trip.
  • If you’re planning to retrace the length of Route 66 as faithfully as we did, you’ll want to arm yourself with as many Route 66 guidebooks and maps as you can find. Having multiple sources to refer to is often the only way to track down the old road’s real hidden gems.
  • While it’s certainly possible to drive Route 66 in either direction, you’re likely to find that traveling east-to-west is easier because the maps and directions in most guidebooks are laid out this way.