Route 66 is celebrating its 100th anniversary in 2026. The American Association of State Highway Officials adopted the United States numbered highway system, including Route 66, on November 11, 1926. Centennial exhibitions and events are taking place across Illinois throughout the year, culminating in a statewide celebration in Springfield on November 11, 2026.
Several of the year’s biggest celebrations have already happened, but some of the most important are still ahead. This guide lists confirmed upcoming events as of September 8, 2026, and links directly to official organizers for current schedules, admission information and any changes. Event details can change — always verify with the official event page before traveling.
The first hundred miles of Illinois Route 66 run from downtown Chicago through the southwest suburbs — including Countryside — before continuing toward Springfield and St. Louis. If you’re planning a centennial trip from the Chicago side, this guide covers what’s confirmed.
Upcoming Illinois Route 66 Centennial Events
The events below were confirmed through official tourism, organizer or government sources on September 8, 2026. Registration, ticket availability and individual schedules may change.
| Date | Event | Location | What to know |
|---|---|---|---|
| Sept 25–27, 2026 | 25th International Route 66 Mother Road Festival | Downtown Springfield | Vintage vehicles, live music and centennial programming; free admission for spectators |
| Oct 8–10, 2026 | Miles of Possibility Route 66 Conference | Springfield | Sessions on Route 66 history, preservation and tourism |
| Oct 9–11, 2026 | Last 100 Miles Festival | Multiple southwest Illinois communities | Community events, music, food and heritage activities from Mt. Olive to Collinsville |
| Nov 11, 2026 | Illinois Route 66 Statewide Conference & Centennial Celebration | Route 66 Motorheads, Springfield | Daytime conference plus an evening centennial concert |
| Through Apr 4, 2027 | “Miles of Memories: Stories of Route 66” exhibit | Illinois State Museum, Springfield | Oral-history exhibit built from 100 personal accounts, with vintage memorabilia |
Official sources: Mother Road Festival · Miles of Possibility · Last 100 Miles Festival · Statewide Centennial Celebration · Miles of Memories exhibit.
Centennial Events That Have Already Taken Place
Illinois marked the centennial earlier in 2026 with its own road trips, exhibitions, community festivals and special programming. The Illinois State Fair’s Route 66 Experience ran August 13–23 in Springfield, with the fairgrounds putting the road at center stage alongside the Legends Neon Sign Park, a permanent collection of restored roadside neon. These are kept here as part of the centennial record, not as upcoming travel recommendations.
Where Does the Centennial Route Begin in Chicago?
Route 66 now has three relevant Chicago starting locations. Navy Pier was designated a new symbolic centennial starting point in 2026, creating a ceremonial pier-to-pier connection with Santa Monica. The familiar “Begin Historic Route 66” sign remains near Adams Street and Michigan Avenue, while the original 1926 eastern terminus was at Jackson Boulevard and Michigan Avenue.
Travelers should choose the location that matches the story they want to experience rather than treating all three as the same historical designation. Read our complete guide to Route 66’s three Chicago starting points.
Route 66 Monuments and Centennial Markers
New and existing Route 66 monuments can be found across Illinois, but installation status varies by community. Some locations are complete, while others remain planned or are being added through separate projects.
Countryside appears in the Route 66 Centennial Monument Project’s destination listings. We recommend confirming the monument’s installation status and exact location with the City of Countryside before treating it as a visitor stop.
Planning the First Part of an Illinois Route 66 Trip
Travelers beginning in Chicago can follow historic alignments southwest through communities such as Cicero, Berwyn, Countryside and Joliet before continuing toward central Illinois. Route 66 changed alignments over time, and modern roads don’t always follow one uninterrupted historic route — use a current official Route 66 map and navigation guidance rather than a short list of road names.
| Planning question | What to check |
|---|---|
| Which alignment will you follow? | Route 66 used different alignments in different periods |
| Which Chicago start will you visit? | Navy Pier, Adams Street or the original Jackson Boulevard location |
| Which attractions are open? | Seasonal hours and restoration work can affect access |
| Are event tickets required? | Conferences and special programs may require advance registration |
| Where will you stay? | Choose accommodation around the complete itinerary |
| How long should you allow? | Stops, events and city traffic can substantially change journey time |
Read our complete guide to Route 66 attractions through Illinois.
Staying on Historic Route 66 in Countryside
William Tell Hotel sits along the historic Route 66 corridor at 6201 Joliet Road in Countryside, IL.
Check Availability
William Tell Hotel MOD Collection by Sonesta is located at 6201 Joliet Road in Countryside, along the historic Route 66 corridor. Its location may suit travelers exploring the Chicago and southwest suburban portion of the route.
The William Tell Restaurant is documented in Countryside from 1974. The hotel’s own opening year remains under historical review, so we don’t describe the property as operating as a Route 66 hotel since that date — read the documented history for what’s confirmed so far.
Travelers can explore guestrooms, on-site dining and current availability through the hotel’s own pages: Explore Rooms & Suites, visit Tell’s Tavern, or check availability directly.
FAQ
When is the Route 66 centennial?
Route 66’s centennial is being celebrated throughout 2026. November 11, 2026 marks 100 years since the American Association of State Highway Officials adopted the United States numbered highway system that included Route 66.
What Route 66 centennial events are still happening in Illinois?
As of September 8, 2026, upcoming events include the International Route 66 Mother Road Festival (September 25–27), the Miles of Possibility Conference (October 8–10), the Last 100 Miles Festival (October 9–11), and the Illinois statewide centennial celebration (November 11). Verify details with each organizer before traveling.
Where is the Illinois Route 66 Centennial Celebration?
The statewide conference and centennial celebration is scheduled for November 11, 2026 at Route 66 Motorheads in Springfield, Illinois. Check the official event page for current tickets and timings.
Where does Route 66 start in Chicago?
Navy Pier became a symbolic centennial starting point in 2026. The familiar “Begin Historic Route 66” sign remains near Adams Street and Michigan Avenue, and the original 1926 eastern terminus was at Jackson Boulevard and Michigan Avenue.
Are Route 66 centennial monuments installed throughout Illinois?
Monument status varies by community. Some markers are installed, while others remain planned or are part of separate local projects — check with the relevant community or tourism source before visiting a specific monument.
Can I visit Route 66 attractions from Chicago in one day?
Some Chicago-area and southwest suburban stops can be combined in a day, but the practical itinerary depends on the alignment you follow, attraction hours, event schedules and traffic. A longer trip allows time to see more of the Illinois route.
Is William Tell Hotel located along historic Route 66?
William Tell Hotel is located at 6201 Joliet Road in Countryside, along the community’s historic Route 66 corridor. Use a current Route 66 map when planning the specific alignment you want to follow.
Where can I find current Illinois Route 66 events?
Check the Illinois Route 66 Scenic Byway calendar and the Enjoy Illinois Route 66 events page for current event dates, locations and organizer information.