Description

Road

Distance - approx. 350 miles

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!

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

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.

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

Registration

We are still developing this new tour and registration is not yet open yet. Please visit https://www.bicycleillinois.com/overall/contact/e-mailsignup.htm to join our mailing list and stay up to date on all the latest news and announcements!

Tour pricing has not yet been finalized, but it will be in line with other fully supported bicycle tours in the region that include hotel accommodations.

Contact

Robert Layton

bicycleillinois@bicycleillinois.com

(877) TOUR-ILL [868-7455]