The sign for the start of the historic route 66 highway in downtown Chicago. (IStock photo by James Andrews)
Chicago is giving the Mother Road a new beginning. In honor of the 100th anniversary of Route 66, the City of Chicago has announced that Navy Pier will be formally recognized as the starting point of the historic roadway, reinforcing the city’s role as the eastern anchor of one of America’s most storied highways.
Mayor Brandon Johnson called the move a powerful symbol of progress and preservation. He said the designation reflects how Route 66 continues to evolve while honoring its roots, stretching from the shores of Lake Michigan to the shores of the Pacific Ocean and representing the ultimate American journey.
The dedication ceremony marking the new starting point and celebrating the road’s enduring role in American history, culture and adventure will take place March 25. The designation was approved through a resolution introduced by 42nd Ward Alderman Brendan Reilly and adopted by the Chicago City Council in recognition of the route’s centennial anniversary. Reilly described Route 66 as a symbol of dreams and possibility and said designating Navy Pier as the eastern terminus creates a meaningful Pier to Pier connection that captures the spirit of the American journey.
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That Pier to Pier concept adds a poetic bookend to the highway. In 2009, the western endpoint of Route 66 was moved to the Santa Monica Pier. With Chicago’s Navy Pier now serving as the starting point, the route will officially run from one iconic pier to another, linking Lake Michigan to the Pacific Ocean. A new Route 66 sign will be installed at Navy Pier marking it as the Beginning of the Trail and reinforcing Chicago’s role as both a historic origin point and a modern gateway for exploration.
Marilynn Gardner, CEO of Navy Pier, said the roadway has long represented connection and possibility and that the Pier, often described as Chicago’s front porch, is a fitting place to launch the next century of American road trips.
The March 25 celebration will unfold as a daylong event that also coincides with baseball season’s Opening Day, uniting America’s road with America’s pastime. Harry Caray's on Navy Pier will host the 28th Annual Worldwide Toast to Harry Caray, the beloved Hall of Fame broadcaster whose life and legacy are closely tied to the road.
Harry Caray’s CEO Grant DePorter, who played a key role in the City’s decision to designate Navy Pier as the starting point, noted that Harry Caray grew up along Route 66 in St. Louis, learned to drive on the route and later traveled it to Wrigley Field to announce his first baseball game. DePorter said Caray’s life embodied the freedom, optimism and joy of the journey that Route 66 represents.
The Route 66 themed Toast will feature live music and entertainment, including a special performance by Tom Higgenson of the Plain White T's. Guests can also expect classic car displays from the Volo Auto Museum and even alpacas from the Chicago High School for Agricultural Sciences, a nod to the animals travelers might encounter along stretches of Route 66 in Arizona.
Established in 1926, Route 66 spans 2,448 miles from Chicago to Santa Monica, California, earning its nickname as the Mother Road and becoming a lasting symbol of American freedom, innovation and exploration. As it enters its second century, Chicago’s decision to reposition the starting line at Navy Pier adds a new chapter to that legacy while inviting a new generation of travelers to begin their journey at the edge of Lake Michigan.
For updates on event programming and travel information, visit navypier.com and harrycarays.com.







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