Whenever I hear the words “Route 66” I’m taken back to my high school English class days. My teacher was obsessed with John Steinbeck’s book “The Grapes of Wrath.” The story was about a family that journeys along Route 66 with other migrants with the hopes of escaping the Dust Bowl and seeking a better life in California during the Great Depression. Route 66 is often referred to as the “Mother Road.” It originally stretched about 2,448 miles from Chicago to Santa Monica, California. Without me going too far off subject we had a year round homework assignment where we had to create our own version of Route 66 and come up with our own journeys. (Sidenote: I got an A on the assignment and still have it till this day. LOL).
Fast forward to 2026, which marks the 100th anniversary of Route 66. Did you know Chicago is the starting point for Route 66? The traditional starting point is at the intersection of Michigan Avenue and Adams Street (across from the Art Institute). Here you’ll find the famous “Begin Historic Route 66” sign, a popular photo spot for visitors beginning their journey west.
When Route 66 was created, Chicago was a major transportation hub. The route was designed to link the Midwest with the Pacific Coast, helping commerce and tourism grow across the country. For the Centennial celebration Chicago will be hosting events and has officially designated Navy Pier as a symbolic centennial starting point.
This past weekend I did the Choose Chicago Route 66 Neighborhoods by Trolley tour with – Tours with Mike. The one-of-a-kind tour transports you to interesting attractions and small businesses that developed around Route 66. On the tour you’ll experience the highway’s fascinating history and how it has shaped the surrounding communities.
Supplementing this experience, you will have access to webpage with historical photos and more that you can view on your own mobile devices. See you on the Route 66!
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