Our Favorite Roads VIII

June 30, 2026.  Later this year, cities along the 2,400 mile Route 66 "Mother Road" will be celebrating the 100th anniversary of this historic route spanning eight states and connecting Chicago, Illinois and Santa Monica, California.   U.S. Route 66 is historically significant  as a major route for westward migration, especially during the Dust Bowl era of the 1930s, and contributed to the economic development of communities located along its path.  It later faced decline as traffic was diverted to the Interstate Highway System in the mid-20th century.    

The highway was officially removed from the U.S. Highway System in 1985.  Many segments of the former route have been preserved and improved as Historic Route 66, an National Scenic Byway, and incorporated into state and local road systems.

We here in Windbreaker Country are fortunate that Route 66, known locally as Foothill Boulevard, passes directly through our home cities of Rancho Cucamonga, Upland, and Claremont.  Though often quite busy with cars, trucks, and buses, much of the route includes improved and dedicated bike lanes, passing historic landmark buildings and sites.  Ride On!

Historic Cucamonga Service Station, originally constructed in 1915

Thomas Winery Plaza, built on the site of California's oldest winery, 
which was originally established in 1839

Madonna of the Trail monument, Upland, CA,
one of 12 identical monuments located nationwide,
along the National Old Trails Road from 
Maryland to California, and honoring pioneer women. 
The monument is located at the intersection of
Euclid Avenue and Foothill Boulevard (Route 66).