Route 66 XL Metal SignEstablished on November 11, 1926 U. S. Route 66, also known as the Will Rogers Highway, the Main Street of America or the Mother Road, was one of the original highways in the U. S. Highway System. The highway, which became one of the most famous roads in the United States, originally ran from Chicago, Illinois to Santa Monica, California, covering a total of 2,448 miles. It was recognized in popular culture by both the hit song "(Get Your Kicks on)