From Pasadena, Fair Oaks Avenue turns into the Arroyo Seco Parkway – which becomes the Arroyo Seco Freeway, the oldest freeway in California and among the oldest in the United States.
Down the Arroyo Seco Freeway, you enter the city of Los Angeles, the second largest city in the U.S. and the traditional "end point" for the Route 66 "Chicago to L.A." theme. The city itself is huge; it sprawls out over 468 square miles.
L.A. is quite the sports town, as you’d imagine. Year round, you’ll find NBA and NHL games hosted at the Staples Center, MLB action at Dodger Stadium, and, once again as of recently, NFL football at the Los Angeles Memorial Colliseum.
Route 66 follows the Arroyo Seco Freeway to the Sunset Boulevard exit before downtown L.A. For the duration of Route 66's "Golden Age", the road headed up Sunset Boulevard and then Santa Monica Boulevard.
Route 66 follows Sunset Boulevard up through neighborhoods like Los Feliz and Silverlake. At the north end of the Silverlake neighborhood – an area called Sunset Junction – watch for Santa Monica Blvd. (California Route 2) west – follow it, because that's Route 66.
You can continue on Sunset if you wish, which will take you through the heart of West Hollywood and the Sunset Strip; west of the Hollywood Freeway (U.S. 101), you can use any major north-south street to go south and meet up with Santa Monica Boulevard again.
Ah, Santa Monica Boulevard. Route 66 follows it almost all the way to the Pacific Ocean – literally to within blocks of it. This famous road cuts through Hollywood and the independent city of West Hollywood, just south of the Sunset Strip, right through Beverly Hills into West L.A. and Century City, all the way to Santa Monica terminus we've been mentioning since Chicago.
There's an absolute ton to see and do on this stretch – and with traffic on Santa Monica, you should have plenty of time to look around and make up your mind about what you want to do.
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