The ugly truth about America’s most famous road trip

America’s Main Street is as ephemeral as the lore it’s evoked since kicking off in 1926. It exists not as an unbroken stretch of bitumen but in splinters of tar that drift off into prairie grass here, duck beneath thundering overpasses there, dissolve in all manner of forsaken dead-ends. Feted and fabled, it labours fitfully across 3940 kilometres and eight richly storied, deeply contrasting states.

Credit: Jamie Brown

Lack of signage and the fragmentary nature of the road lead to many a wrong turn. The first rule is to get your hands on a reliable map: Route 66 historian Jerry McClanahan’s EZ66 Guide, produced with The National Historic Route 66 Federation, is your faithful companion. Individual alignments and easterly and westerly driving instructions are clarified in this spiral-bound digest.

Direction presents another dilemma: where to start? Purists set off from downtown Chicago – a day’s drive from the route’s official birthplace of Springfield, Missouri – and follow the trail across America’s breadth before sidling to a halt at Santa Monica Pier. One can more easily conjure, on this course, the route’s historic trajectory, and the souls of those who traversed it on their way to the “land of milk and honey” – California – during the Great Depression.

The jalopies cluttering the Mother Road in Steinbeck’s The Grapes of Wrath are long gone. Harley Davidsons and Chevy Corvettes lend a touch of retro authenticity to the modern wayfarer’s journey; whatever your style, remember that the road’s decay demands robustness in a vehicle. And though you could conceivably cover the distance in three or four days, the voyage should proceed sedately, over a period of two weeks or more.

The journey, after all, is the destination; across every arch-truss bridge, forested knoll and ragged ridge a new curiosity springs to life: painted landscapes, state capitols, tattered signposts tempting detours to secret hamlets. Stop at Springfield, Illinois to pay respects to Abraham Lincoln at his family tomb; puzzle over the Cadillacs pinioned head-first into baked earth outside Amarillo, Texas; heed the Grand Canyon’s melancholic call as you approach Flagstaff, Arizona. As night closes over the country’s heartland, check into a motel lit with neon signage, slide into a booth at a roadside diner, and feast on the past.

Finally, come armed with a road-trip playlist. Tom Cochrane’s Life is a Highway, Prince’s Little Red Corvette, Bob Seger and the Silver Bullet Band’s Roll Me Away. Crank the volume and hit the Mother Road. You can go east, you can go west – it’s all up to you to decide.