CYCLES

Documenting stories as we cross America on bicycle.

We aren’t the first people to ride bikes across the country.

It is easy to speak about unity from a distance. It's different to practice it over miles, where movement ignites cooperation, the distance humbles you, fatigue makes you malleable, and on the road, you learn the value of grace quickly.

This ride moves unity toward humanity.

And part of this ride will cover the earth paved over by Route 66.

2026: THE RECON Chicago to St. Louis

The Prologue Route. Approximately 300 miles. Five to six riding days at 50 to 60 miles per day, with flex days built in for weather, community moments, or the unexpected. This is not a race, it is a tuning. Learning to hear the road, the wind, and each other. Every mile is research. Every stop is a conversation.

Chicago to St. Louis. In the Fall of 2026, the four of us will depart the Obama Presidential Center for St. Louis. Documenting the ride, but more importantly those moments we meet new people, share stories over post-ride drinks, or pre-ride coffee and breakfast. The joy is in the connection, and cycling Route 66 is the conduit for those conversations to happen. From this ride, a mini-series 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.

SEGMENT ROUTE
DISTANCE
Get involved · 2026 Prologue

Connection is the goal.

CYCLES is a movement made of people. Ride a single mile, a single day, or the full 300 from Chicago to St. Louis — or help power the road ahead.

Ride with us

You don't need to be an elite cyclist. CYCLES is built for people, not racers — regular folks learning how to move together, one mile at a time.

There are three ways to join the 2026 Prologue: ride the full route from Chicago to St. Louis, come out for a single day on any segment, or host a local ride in your own town while we're on the road. Bring your story and your care — we'll bring the road.

Sign up to ride →
2027: THE GIANT Chicago to Santa Monica

CYCLES 2027 is a 38-day, 2,014.7-mile ride from Chicago to Los Angeles along historic Route 66. It is not a bike ride. It is a movement — rooted in transportation equity, environmental justice, community healing, and the radical belief that art is the catalyst for social change.

The ride centers communities that are often left out — Black and Brown folks, the unhoused, the neurodivergent — but it is ultimately about humanity. All of it.

TOTAL DISTANCE  2,014.7 miles
TOTAL DAYS  38 days · ~60 mi/day
LAUNCH  Chicago, IL · May 15, 2027
ARRIVAL  Los Angeles, CA · June 21, 2027
CYCLES IN CHAPTERS

THE TEAM

Our team is small, and our hearts mighty. CYCLES was instigated by Rob McKay, whose vision — physical and philosophical — pulled in Prashant Vallury, Steve Dobias, and Charles Adler.