Festivals, Fairs & Special Events
28th Annual Worldwide Toast to Harry Caray
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.
Roadmap of the Day:
10:30 a.m. | Route 66 Sign Dedication Ceremony
2:00–6:00 p.m. | WGN Radio Live Broadcast – The Lisa Dent Show
5:30 p.m. | Toast Time!
Special guests taking the wheel for the Route 66-themed festivities include:
- White Sox legend Ron Kittle, who rode his Harley the entire 2,448 miles of Route 66
- Cubs legend Ryan Dempster, performing his Harry Caray impersonation
- 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
- Abraham Lincoln, portrayed by Illinois’ own Richard Klein
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.
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 special performances by the Plain White T’s
- Classic cars on displays including the 1966 Bat Mobile, 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.
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.
