Rules Of The Road: Route 66

Route 66 - Arrows

If I was to lay out my list of most memorable extraordinary experiences, road-trips would occupy some of the top slots.

Take the 2,400-odd miles of historic Route 66 I traveled with a couple of friends a few years back. You’ll find the complete story of that road-trip on page 131 of Extraordinary Experiences, but suffice it to say that—as cool as many of the actual attractions were — it was the sense of anticipation each new sunrise brought that made it a true once-in-a-lifetime adventure.

Rules of the Road: Route 66

If you’re thinking of having your own motoring adventure in the months ahead, here are my Rules Of The Road for getting your kicks on Route 66:

1. Patience Is A Virtue

Look, you’re going to get lost, so expect it. Don’t stress over it though — this is supposed to be fun, remember? We took plenty of wrong turns and still managed to follow Route 66 from Chicago all the way to Los Angeles.

2. Pack A Library

Because following Route 66 faithfully can be tricky, load up on guidebooks and maps. We had a wide selection of both and, though no one publication was perfect, the consensus between them helped us find every mile that was still drivable.

3. Avoid National Chains

Part of the joy of traveling Route 66 is to experience an era of American history you may have thought was gone for good. So spend the night in a teepee motel and have breakfast at an old-school roadside diner. Chances are you’ll be glad you did.

4. No Reservations

Trust me: Leaving your Route 66 itinerary loose allows space for serendipity to deliver extraordinary experiences, things you would likely have missed if you were intent on making it to, say, Amarillo by suppertime.

5. Shoot Lots

You’re not likely to be here again, so give yourself plenty of photos/videos to remember your Route 66 road-trip. From round barns to giant beached blue whales, you’ll discover things the folks back home won’t believe without the pics to prove it!