In celebration of the 100th anniversary of Route 66, the City of Chicago will formally recognize Navy Pier as the starting point of the iconic roadway. “This move symbolizes how Route 66 continues to evolve while honoring its roots,” said Mayor Brandon Johnson. “From the shores of Lake Michigan to the shores of the Pacific Ocean, Route 66 represents the ultimate American journey.”
The dedication ceremony celebrating the new starting point of Route 66 and its enduring role in American history, culture, and adventure will take place on March 25, 2026.
The designation was approved through a resolution introduced by Alderman Brendan Reilly and adopted by the Chicago City Council in recognition of Route 66’s centennial anniversary and Chicago’s historic role as the route’s eastern anchor. “Route 66 has always been about dreams and possibility,” said 42nd Ward Alderman Brendan Reilly. “Designating Navy Pier as the eastern terminus honors Chicago’s historic role while creating a powerful Pier-to-Pier connection that captures the true spirit of the American journey.”
Pier-to-Pier
In 2009, the endpoint of Route 66 was moved one mile west to the Santa Monica Pier. With the starting point moving to Chicago’s Navy Pier, the road, and its travelers, will now run Pier to Pier. An impressive new Route 66 sign will be installed at Navy Pier marking it as the Beginning of the Trail. The Pier-to-Pier connection creates a symbolic bookend to one of America’s most storied highways, linking Lake Michigan to the Pacific Ocean and reinforcing Chicago’s role as both a historic origin point and a modern gateway for exploration.
“Route 66 has long represented connection and possibility, and we’re proud that its journey now begins at Navy Pier,” said Marilynn Gardner, CEO of Navy Pier. “As Chicago’s front porch and a gateway to the city, Navy Pier is a fitting starting point to honor 100 years of American history, culture, and travel.”
Daylong Celebration
The celebration also coincides with baseball season’s Opening Day, fittingly uniting two great American traditions: America’s road and America’s pastime. As part of the daylong festivities, Harry Caray’s on Navy Pier will host the 28th Annual Worldwide Toast to Harry Caray—an annual event celebrating the life of the beloved Hall-of-Fame announcer.
“Harry Caray’s life perfectly embodied the spirit of Route 66 — freedom, optimism, and the joy of the journey,” said Harry Caray’s CEO Grant DePorter, who was instrumental in the City’s decision to make Navy Pier the starting point for Route 66. “Harry grew up along Route 66 in St. Louis, learned to drive on Route 66, and took route 66 to Wrigley Field to announce his very first baseball game. It’s incredibly meaningful that the road now begins at Navy Pier, where we gather each year to celebrate him.”
The Route 66 themed Toast will feature a lineup of “roadside attractions” including live music and entertainment with special performances by Tom Higgenson of the Plain White T’s; classic car displays from Volo Auto Museum; alpacas from the Chicago High School for Agricultural Sciences, representing those found along Route 66 in Arizona; and more.
For updates on event programming and travel information, visit navypier.com and harrycarays.com.