(in front of Pasadena High School)
Explore Washington Boulevard from Sierra Madre Boulevard to Fair Oaks Avenue – a significant tour of central Pasadena. There are lots of interesting old and new businesses especially on this route.
About 3.8 miles one way, double that if you do it round trip. (or Bus #268 can take you back near PHS – Orange Grove/Sunny Slope).

La Pintoresca Hotel, Pasadena CA. Image courtesty the Pasadena Digital History Collaboration (http://pasadenadigitalhistory.com)
Some things I’ve learned about Washington Boulevard from Wikipedia: Washington Boulevard was constructed in the early 20th Century to facilitate vehicular access to the Hotel La Pintoresca at Fair Oaks & Washington, and to service riders on the East Washington Streetcar line. The line ran for 2.5 miles between Los Robles Avenue and Santa Anita Avenue. Washington Boulevard originally terminated at Arroyo Boulevard and Altadena Drive. An extension west to Linda Vista was built in the 1940s and another southeast to Pasadena High School in the 1960s.