It winds from Chicago to L.A.,
More than two thousand miles all the way.
Get your kicks 
on Route 66.

Bobby Troup got the idea for that song from his wife, Cynthia, back in 1946. The pair was headed for California, where Mr. Troup hoped to become a songwriter. 

In the end, Mr. Troup didn’t just write a song. He wrote a map. The song “(Get Your Kicks On) Rout 66” traces major points along the now-famous road.

The Troups started their journey in Pennsylvania. By the time they reached Los Angeles, Mr. Troup had half-finished the tune. About a week later, he got to pitch some songs to Nat King Cole. Mr. Cole was already a famous singer. He loved the song. He went on to record it—as would other famous musicians in the decades to come.

More Than a Highway

When designing their stamps, Mr. Schwartz and Mr. Breeding wanted the route to look the way it really is. Colorful. Quirky. Old. 

Mr. Schwartz hopes the new stamps inspire people to visit Route 66 for themselves, support its mom-and-pop businesses, and keep it humming for another 100 years. There’s no other road like it.

Eventually, people built freeways across the same area Route 66 traverses. That made travel faster and easier. But an interstate can’t offer the kinds of views Route 66 does. Why not?

Because “you’d probably get run over,” Mr. Schwartz jokes. Plus, “interstates are designed to move traffic quickly. They cut through the sides of mountains. They do not follow the contour of the land.”

Not so on Route 66. There, “you’re actually part of the landscape as you move through it,” Mr. Schwartz says. “You feel the land as you’re traveling.”