Edwardsville Route 66 Festival
Location: 101 S. Buchanan St, Edwardsville, IL 62025
When: June 13, 2026 | 8 AM - 11:30 PM
Edwardsville's Route 66 Festival celebration makes for a whole day of fun. For runners, the event starts with a Route 66 10K, followed by the opening of the festival doors. Grab a seat in the audience to the live music performed, stroll through the car show, and cheer on drivers at the cruise. Learn more here.
Pink Elephant Antique Mall Route 66 Centennial Celebration
Location: 908 Veterans Memorial Dr, Livingston, IL 62058
When: June 20, 2026 | 10 AM - 8 PM
The Pink Elephant Antique Mall will be hosting a series of events in honor of its 100th birthday. The day starts with a Jeep Duck Hunt with a $5 entry fee. At 3 PM, the Route 66 Centennial Cruise-In begins, a car show that welcomes vehicles and spectators for free. There will also be a pinup contest, bouncy castles, and so much more for guests to enjoy.
The Hemmings Great Race | Collinsville Stop
Location: Uptown Collinsville
When: June 20, 2026 | 4 PM - 7 PM
The Hemmings Great Race's second stop is here in Collinsville! Cheer on drivers or join fellow gearheads on a ride across the states. Following Route 66, The Hemmings Great Race will navigate participating vehicles from Illinois, through Missouri, Oklahoma, New Mexico, Texas, Arizona, and Nevada before ending in California.
For those looking to join the race, find more information here on how to register.
Catsup Bottle Festival
Location: Herald Square | 113 E Clay St, Collinsville, IL 62234
When: June 20, 2026 | 2 PM - 7 PM
While in Collinsville for the Hemmings Great Race, swing by the Catsup Bottle Festival! See the Giant Potato Truck in person and continue your Route 66 experience with the Catsup Bottle Festival Classic Car Show.
Route 66 Jubilee
Location: Macoupin County Courthouse | 201 E Main St, Carlinville, IL 62626
When: June 26, 2026 | 9 AM - 10 PM
Plan to fill your day with retro cars, educational talks, and community fun with the Route 66 Jubilee. Cars will be on display all day while car enthusiasts and historians give presentations on the role of the vehicles in American life, but that won't be all. Carlinville also wants to pay tribute to the local talent and will have songwriters, singers, and musicians from the community performing their original music all day.
Wildey Theater Showing
Location: 252 N. Main St. Edwardsville, Illinois 62025
When: September 10, 2026
Take the time to celebrate the centennial in retro style with this vintage-loving event. Catch a screening at the historic Wildey Theater in Edwardsville. A long-time collaborator with Route 66, the theater is expected to schedule a screening of a car-themed film. Learn more here.
Bicycle Illinois Route 66 Ride
Location: Starts in Madison County
When: September 19 - 23, 2026
Madison County takes a different kind of wheel to Route 66: bike wheels. The bicycle ride will take participants through timed trails in Collinsville, Granite City, Edwardsville, Hamel, and Troy. Pack your helmet and grab your water to prepare for this athletic event.
