 Route 66 is decertified. After 59 years, the iconic Route 66 enters the realm of history on this day in 1985. The American Association of State Highway and Transportation Officials decertifies the road and votes to remove all the highway signs. Measuring some 2,200 miles in its heyday, Route 66 stretched from Chicago to Santa Monica, right there at the Santa Monica Pier in California, passing through eight states.