Toast To Harry Caray

HARRY CARAY’S on NAVY PIER
700 EAST GRAND AVENUE

Join us for the 28th Annual Worldwide Toast to Harry Caray on Wednesday, March 25th! This year’s Toast brings guests along for the ride as Chicago marks a new beginning for an iconic American journey with the official designation of Navy Pier as the new starting point of historic Route 66.

Timed to coincide with both the 100th Anniversary of Route 66 and Opening Day of baseball season, this year’s celebration ties together two great American traditions — the open road and America’s pastime — through the larger-than-life spirit of another timeless American icon, Harry Caray.

Special guests taking the wheel for the Route 66-themed festivities include:

Cubs legend and Master of Ceremonies Ryan Dempster, performing his Harry Caray impersonation
White Sox legend Ron Kittle, who rode his Harley the entire 2,448 miles of Route 66
7-foot-2 former Bulls announcer Tom Dore, appearing as the Gemini Giant — a fiberglass roadside statue located in Wilmington, Illinois, along Route 66
Chicagoland-native pop rock band the Plain White T's
Mark Martin, NASCAR Hall of Fame driver
Abraham Lincoln, portrayed by Illinois’ own Fritz Klein
Matt Wagner, Harry Caray impersonator

The roadmap for the day begins at 10:30 a.m. with an official Route 66 Sign Dedication Ceremony on the South Dock of Navy Pier, just east of Harry Caray's patio. The City of Chicago will formally unveil the new sign that designates Navy Pier as the Beginning of the Trail and creates a symbolic pier-to-pier journey from Navy Pier in Chicago to the Santa Monica Pier in California. The ceremony will conclude with a special performance by Chicagoland-native pop rock band, The Plain White T’s.

Expected Attendees for the Sign Dedication Ceremony Include:

Alderman Brendan Reilly, sponsor of the Route 66 initiative
Alderman Brian Hopkins, member of Illinois’ first Route 66 Commission
Alderman Matt O’Shea
Marilynn Gardner, CEO of Navy Pier, Inc.
Catie Sheehan, Deputy Director of the Illinois Office of Tourism
Kristen Reynolds, President & CEO of Choose Chicago
Sam Toia, President & CEO of the Illinois Restaurant Association
Bob Reiter, President Chicago Federation of Labor
Kimberly Bares, President & CEO of The Magnificent Mile Association
Cory Jobe, Chair of Illinois’ Route 66 Centennial Celebration Commission
Casey Claypool, Executive Director of Illinois Route 66 Scenic Byway
Bill Thomas, Commissioner - U.S. Route 66 Centennial Commission
Robert Navarro, President & CEO of Heritage Corridor Convention & Visitors Bureau
Jim Harris, Executive Director at Santa Monica Pier
Deborah Gershbein, President Streeterville Organization of Active Residents
Grant DePorter, President & CEO of Harry Caray’s Restaurant Group

The celebration reaches the finish line at 5:30 p.m., with the Toast to Harry, when fans raise a Budweiser to the legendary sports icon whose life perfectly embodied the spirit of Route 66 — freedom, optimism, and the joy of the journey.

Guests can look forward to a full lineup of “roadside attractions” present throughout the day, including:

Live music and entertainment, featuring a special performance by the Plain White T’s
Classic cars on display including the 1966 Batmobile, a 1933 Ford Custom Woody, a 1955 Chevy, and a 1966 Ford Mustang Convertible; courtesy of Volo Auto Museum
A new Route 66-themed mural in the atrium of Harry Caray’s Navy Pier
Alpacas from the Chicago High School for Agricultural Sciences, representing those found along Route 66 in Arizona.

Vertical Divider

ROADMAP FOR THE DAY
Wed. MARCH 25, 2026

10:30am
Route 66 Sign Dedication
Ceremony
Marking Navy Pier as the official starting point of Route 66

2:00PM-6:00PM
WGN RADIO LIVE BROADCAST
THE LISA DENT SHOW

5:30PM
Toast Time!

WGN Radio’s The Lisa Dent Show will broadcast live from 2:00 PM – 6:00 PM, featuring special appearances by some of the celebrity guests who will be take the stage for the official Toast to Harry at 5:30pm.

Fans who can’t attend in person can listen live on WGN Radio 720 in Chicagoland or stream online at wgnradio.com.