Riding Historic U.S. Route 66 from Chicago to Missouri

Vintage postcard showing the location of Route 66, The Main Street of America

Route 66 was one of the country's first continuous stretches of paved highway, and served as a major path for those who migrated west.

"The Mother Road" was established on November 11, 1926, and ultimately stretched 2,448 miles from Chicago to Los Angeles.

The beginning point of Route 66 has changed a few times over the years, originally starting on Jackson Boulevard at Michigan Avenue.

From its beginning in Chicago, Route 66 and ran southwest to Bloomington and on to Springfield, Illinois.

Leaving Springfield, it took a more southerly route to St. Louis, where it turned west through Rolla, Springfield, Joplin and into Oklahoma.

We've driven much of Route 66, including segments in Illinois and Missouri. And ... don't miss Shea's when in Springfield, Missouri!

Photo Highlights from Our Road Trips Along Route 66

We have included below a sampling of the original photographs taken by our staff. We are working to post more photographs and reviews from our road trip archives to this website over time.

Shea's in Springfield Illinois, along Historic Route 66
Shea's in Springfield Illinois, along Historic Route 6

Murals on the wall in downtown Cuba, Missouri, on Historic Route 66
Murals on the wall in downtown Cuba, Missouri, on Historic Route 66

Downtown Cuba, Missouri, on Historic Route 66
Murals on the wall in downtown Cuba, Missouri, on Historic Route 66

Prosperity Corner mural, Cuba, Missouri, on Historic Route 66
Murals on the wall in downtown Cuba, Missouri, on Historic Route 66

Vintage Postcard: Victory Court, Springfield, Missouri, on Historic Route 66
Victory Court, Springfield, Missouri, on Historic Route 66

Vintage Postcard: Modern Cottages, Rolla, Missouri, on Historic Route 66
Modern Cottages, Rolla, Missouri, on Historic Route 66


Travel Reviews of the Sections of Historic Route 66

Planning a Road Trip on Route 66? Here are the major segments ...

Route 66: The Mother Road - Introduction

Route 66: Chicago to Missouri

Route 66: Across Oklahoma to Amarillo

Route 66: Amarillo to Santa Fe

Route 66: Santa Fe to Gallup NM

Route 66: Gallup NM to Seligman AZ

Route 66: Seligman to Kingman AZ

Route 66: Kingman to Oatman AZ