Route 66 (1926 - present) In 1926, a major highway was completed connecting Chicago and Santa Monica. Bearing the designation US Route 66, it covered 2,448 miles and passed through eight states. Route 66 was THE major route for vehicle travel from the populated areas of the Midwest to Southern California. The Route still exists and passes through San Bernardino on its way to Santa Monica where it ends. San Bernardino was made quite famous by all of the excitement of the “Mother Road” and was the destination to "get your kicks on Route 66." During the third weekend in September, the Route comes alive as San Bernardino celebrates with the annual "Route 66 Rendezvous." The Rendezvous is a four-day, three-night cruising car festival featuring over 1,900 classic and custom vehicles. This event draws over 500,000 spectators who come to experience music, food, family fun and classic cars in historic downtown San Bernardino.