Route 66: Photos from the ‘Main Street of America'

It was created to connect us, a 2,448-mile gateway to vast lands that previously existed only in the collective imagination. Each mile promised freedom and escape, opportunity and adventure.

Route 66, "The Main Street of America."

There is perhaps no better-known highway anywhere in the world. In its 100-year history, it has offered safe passage to Dust Bowl refugees, World War II transports and vacationing families. John Steinbeck called it "the mother road, the road of flight." Nat King Cole crooned about its kicks in a 1946 hit song. Disney and Pixar took inspiration from it for a 2006 blockbuster.

Despite being decommissioned in 1985 in favor of a faster and wider interstate highway system, Route 66 continues to capture our imaginations in the remnants of its past glory that remain today.

As the iconic road celebrates its centennial this year, the Chicago Tribune set out across Route 66 to find the stories it holds, introducing readers to the people and places it was designed to connect: the colorful characters and roadside oddities, the business owners trying to revitalize their pieces of history and the ever-changing vistas that continue to define this famed highway.

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This story was originally published May 25, 2026 at 1:42 AM.