Dedication Ceremony for Historic Route 66 New Starting Point at Navy Pier

As Route 66 turns 100, the City of Chicago is marking the milestone in a big way—by officially designating Navy Pier as the new starting point of the Mother Road.

The dedication ceremony takes place March 25, 2026, at 10:30 a.m. on Navy Pier’s South Dock (N Breakwater Access, Chicago Loop). After remarks from city leaders and special guests, dignitaries will unveil a new Route 66 “Beginning of the Trail” sign, formally establishing a Pier-to-Pier connection from Lake Michigan to the Pacific Ocean.

The designation was approved by the Chicago City Council through a resolution introduced by 42nd Ward Alderman Brendan Reilly, recognizing Chicago’s historic role as Route 66’s eastern anchor. With the western endpoint located at Santa Monica Pier since 2009, the highway will now officially run Pier to Pier—linking Navy Pier to the Pacific in a symbolic bookend to one of America’s most storied roads.

Featured Guests & Appearances

Attendees and participants include:

• 42nd Ward Alderman Brendan Reilly
• 2nd Ward Alderman Brian Hopkins
• Marilynn Gardner, CEO of Navy Pier, Inc.
• Kristen Reynolds, President & CEO of Choose Chicago
• Cory Jobe, Chair of Illinois’ Route 66 Centennial Celebration Commission
• Grant DePorter, CEO of Harry Caray’s Tavern – Navy Pier
• White Sox legend Ron Kittle, who rode his Harley the full 2,448 miles of Route 66
• Cubs legend Ryan Dempster performing his Harry Caray impersonation
• Former Bulls announcer Tom Dore appearing as the Gemini Giant (the famed fiberglass statue in Wilmington, Illinois)
• Tom Higgenson, lead singer of the Plain White T’s
• Abraham Lincoln portrayed by Illinois’ own Richard Klein

Following the unveiling, Illinois band Plain White T’s will perform live. The group is inducted into the Illinois Rock & Roll Hall of Fame, located along Route 66 in Joliet.

A Full Day of Celebration

The festivities continue throughout the day with classic car displays from the Volo Auto Museum, vintage Route 66 memorabilia, live music, and even alpacas from the Chicago High School for Agricultural Sciences—a nod to the desert stretches of Arizona along the route.

WGN Radio will broadcast live from Harry Caray’s at Navy Pier from 2–6 p.m. as part of the 28th Annual Worldwide Toast to Harry Caray, with the official toast at 5:30 p.m. The date also coincides with Opening Day of baseball season, bringing together two great American traditions: the open road and America’s pastime.

With the new starting point sign installed at Navy Pier, Route 66’s centennial celebration reinforces Chicago’s role as both the historic beginning of the trail and a modern gateway for exploration. From the shores of Lake Michigan to the Pacific Coast, the Mother Road continues to connect generations—now, officially, Pier to Pier.