Where It Goes: America's most famous highway, Route 66, travels from the greater Chicago area all the way to Los Angeles. Along the way, it dots through Missouri, Oklahoma, Texas, New Mexico, Arizona, and California.
Length: 2,451 miles
Driving Time: about two weeks
Where to Stop: A better question would be "Where to begin?" Route 66 offers a nearly unlimited number of sites and cities to visit. Check out Cadillac Ranch, just west of Amarillo, Texas, an iconic piece of art that's literally graffiti-covered Cadillacs poking out of the Texas desert. Continue on into Arizona and spend a little time at the Dollar Bill Bar in Oatman, Arizona. And if you're feeling thirsty once you've finally reached the Golden Coast, stop in Fair Oaks Pharmacy and Soda Fountain in Pasadena for a step back in time, and a soda pop.