Get Your Kicks On Route 66 Route 66 is a classic American road trip that riders from around the world undertake every year on street and dual purpose bikes. This page is dedicated to preparing riders for a successful and fun trip. Incepted in 1926, Route 66 extends from Chicago, IL. to Santa Monica, CA. There is much to see across the eight Route 66 states and lots of friendly folks to visit with. This is the Offical Route 66 post. Help others get ready for a trip down "The Mother Road". Ask a planning question or leave information for others here.