As Route 66 marks its 100th anniversary, Chicago has officially redesignated the historic highway’s eastern starting point, moving it to Navy Pier along the shores of Lake Michigan. The decision transforms the iconic roadway into a symbolic pier-to-pier journey, stretching from Navy Pier to the Santa Monica Pier in California.
The change was approved by the Chicago City Council following a resolution introduced by Alderman Brendan Reilly. For decades, the route’s starting marker had been located at the intersection of Michigan Avenue and Adams Street. By relocating it to Navy Pier, city leaders aim to reinforce Chicago’s role as the historic eastern anchor of Route 66 while creating a more visually and symbolically powerful origin point on the waterfront.
Mayor Brandon Johnson described the move as both a tribute to the road’s heritage and a sign of its continued evolution. Established in 1926, Route 66 once served as a critical artery for Americans heading west, particularly during the Dust Bowl migration of the 1930s.
Spanning approximately 2,448 miles, the highway became embedded in American literature, music and popular culture before being largely replaced by the Interstate Highway System. Since the 1980s, Historic Route 66 designations have helped revive its tourism appeal.
A Pier-to-Pier American Journey
The relocation aligns the eastern starting point with the western endpoint, which was moved in 2009 to the Santa Monica Pier. With Navy Pier now serving as the official beginning of the trail, travelers can experience a clearly defined coast-to-coast journey from Lake Michigan to the Pacific Ocean.
An official Route 66 sign marking the new starting point will be unveiled on March 25, 2026. The ceremony coincides with Opening Day of the baseball season and the 28th Annual Worldwide Toast to Harry Caray, a beloved broadcaster closely associated with Chicago sports culture. Caray’s personal connection to Route 66 adds historical resonance to the event, as he grew up along the route and traveled it early in his career.
Centennial Celebrations and Cultural Programming
The dedication ceremony at Navy Pier is planned as a daylong celebration reflecting the spirit of classic roadside Americana. Programming will include live music performances, classic car displays and exhibits featuring Route 66 memorabilia. Special guests are expected to include local officials, tourism leaders and cultural figures connected to the centennial celebration.
Navy Pier, one of the Midwest’s most visited tourism destinations, welcomes millions of visitors annually. By designating it as the new eastern terminus, Chicago reinforces its waterfront landmark as both a historic symbol and a modern gateway for travelers beginning their cross-country journey.
With the centennial milestone, the Route 66 relocation underscores how heritage tourism continues to evolve. The pier-to-pier framing not only strengthens the narrative of the “ultimate American road trip,” but also repositions Chicago’s lakefront as the literal starting line of one of the nation’s most storied highways.
