ROUTE 66
Sat. September 19th - Sat. September 26th, 2026

Introducing the new Route 66 Ride!

Route 66 is Bicycle Illinois's newest week long cycling tour from the St. Louis area to Chicagoland along the legendary Old Route 66!

Please note that we are still developing this new tour and registration is not yet open yet.
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Experience the Mother Road on Two Wheels
Pedal along historic Route 66 from St. Louis to Chicago and discover a scenic journey through quaint Midwestern towns, open farmland, and classic roadside attractions. Follow the nostalgic charm of the Mother Road, where vintage gas stations, diners, museums, and glowing neon signs bring America’s golden age of travel to life.

With its gentle terrain and lightly traveled roads, this route offers a relaxed yet rewarding cycling adventure. Every mile reveals a blend of Americana history, local hospitality, and the timeless satisfaction of riding a truly legendary road.

Join us for this fully supported, all-hotel tour - the perfect way to celebrate the 100th anniversary of Route 66 and America’s 250th birthday in unforgettable cycling style!

Stay tuned - more details and registration information will become available as our plans continue to progress!

Route Information
We are still in the process of determining the specific cycling route we will follow, but we will ride directly on the various alignments of the original Route 66 as much as possible whenever it is safe and enjoyable for bicycling. It will not be possible to travel every mile of the original Route 66 however, as many sections remain active roadways with heavy truck traffic, such as I-55 and Memorial Parkway in Springfield. Click Here for a map showing the alignments of Route 66 we are using as the backbone for the route.

We are also working with various local Route 66 authorities to identify the historic, unique, and quirky attractions along the route that make Route 66 so special. Many of these sites will also serve as stops along the way, allowing you to experience them firsthand from your bike!

We are planning on seven stopping towns, two arrival/transportation days, and six or seven days of riding. Below are the very tentative dates, stopping towns, and approximate daily distances:

• Saturday, September 19th, 2026 - arrival & optional transportation day
  • Optional transportation service from Joliet to Edwardsville for you, your bike, and your baggage
  • Arrival in Edwardsville
  • Optional loop ride from Edwardsville to St. Louis over the Old Chain of Rocks Bridge - 35 miles
• Sunday, September 20th, 2026 - 45 miles
  • Edwardsville to Litchfield
• Monday, September 21st, 2026 - 55 miles
  • Litchfield to Springfield
• Tuesday, September 22nd, 2026 - Layover Day, attractions and mileages to be determined
  • Layover day in Springfield: Hop on your bike and visit many of the historic Abraham Lincoln sites!
• Wednesday, September 23rd, 2026 - 50 miles
  • Springfield to Lincoln
• Thursday, September 24th, 2026 - 55 miles
  • Lincoln to Bloomington-Normal
• Friday, September 25th, 2026 - 80 miles
  • Bloomington-Normal to Dwight
• Saturday, September 26th, 2026 - 60 miles
  • Dwight to Joliet
• Sunday, September 27th, 2026 - optional transportation day
  • Optional transportation service from Joliet to Edwardsville for you, your bike, and your baggage

Total mileage - approximately 350 miles, an average of about 60 miles per day

Please note: All stopping towns and mileages are subject to change as the route is finalized.

Tour Services
The tour will be fully supported and registration will include all of the services you need:

• Hotel lodging every night
• Always available "on call" SAG vehicle support service
• Baggage transportation between stopping towns
• The route which will follow the original alignments of old Route 66 as much as possible
• Interesting and historic attractions along the way to stop and experience first hand such as museums, diners, gas stations, motels, etc.
• Navigation via Ride With GPS app
• The availability of mechanical support services for your bicycle on the road (parts and labor for bicycle repairs are extra)
• A complimentary pair of Bicycle Illinois and Bike Wisconsin cycling socks!

The following extra optional services and merchandise will be available as well:

• Transportation service from Joliet to the St. Louis area for you, your bike, and your baggage on an Amtrak train both before the start and after the end of the tour
• Long term parking in Joliet or the St. Louis area
• Bicycle Illinois merchandise including:
  • Jerseys
  • Water Bottles
  • T-shirts
  • Baseball hats
  • Polo shirts
  • Extra cycling socks

You will be reponsible for the following on your own:

• Lunch on the road in one of the small towns we pass through
• Dinner in our nightly stopping towns after the end of each day's ride

Depending on feasibility and interest levels, future years may also include establishing a route from Joliet to Chicago and/or offering indoor and outdoor camping options at main lodging sites in our nightly stopping towns.