CYCLES
Documenting the stories of Route-66 by bicycle.
Some roads carry more than traffic.
Route 66. The iconic highway is more than a road. It tells the story of America, its trials and tribulations, innovations and adventures. A monument of connection, displacement, and the communities that follow its path.
In 2027, we will ride its entirety. Beginning in Chicago all the way to Los Angeles. 2,014.7 miles. 8 states. Countless days. But the goal isn't the distance. We're not checking off a bucket list or defining ourselves by the watts we output. Our goal is connection. Through discussions, debates, meals, and yes, even riding bicycles together with the people along the way that make up the communities of this precious piece of American history.
We ride to uncover the hidden stories of past, present and future of this country. To understand ourselves a bit better, and share those stories with anyone else curious as we are, to listen.
The Recon
The roads of Route 66 are dying and decaying. Some are ruins of their past, particularly when leaving Chicago. So we've opted to use 2026 as a reconnaissance ride. To understand the road that we're navigating. The understand ourselves, and to grow awareness for the mission of our larger endeavor.
Chicago to St. Louis
In the Fall of 2026, the four of us will depart Chicago's famed Millennium Park for St. Louis.
Documenting the ride, but more importantly those moments we meet new people, share stories of post-ride drinks, or pre-ride coffee and breakfast. The joy is in the connection and cycling Route 66 in the conduit for those conversation to happen. From this ride, a mini-series that begins to unfold the stories, while also preparing ourselves for the larger task ahead. Our recon will lay the groundwork for what's to come.
The Route
| Segment | Route | Distance | Anchor Towns |
|---|---|---|---|
| 01 | Chicago (Grant Park) | — | Departure point |
| 02 | Chicago → Joliet | ~35 mi | Elwood, Wilmington |
| 03 | Joliet → Dwight | ~55 mi | Odell, Gardner |
| 04 | Dwight → Pontiac | ~45 mi | Odell, Lexington |
| 05 | Pontiac → Bloomington-Normal | ~50 mi | Pontiac, Towanda, Normal |
| 06 | Bloomington-Normal → Springfield | ~55 mi | Lexington, Lincoln, Springfield |
| 07 | Springfield → Litchfield | ~50 mi | Auburn, Litchfield, Carlinville |
| 08 | Litchfield → St. Louis | ~45 mi | Collinsville, East St. Louis, Chain of Rocks Bridge |
Stay in the loop.
Get updates on the 2026 reconnaissance ride and the full 2027 journey.