Route 66 Centennial Tour
16-Day Guided Adventure — Chicago to Santa Monica
A once-in-a-lifetime journey celebrating 100 years of America's most iconic highway. Eight states. 2,210 miles. The original Mother Road.
Duration
16 Days / 15 Nights
Distance
2,210 miles / 3,536 km
Start / Finish
Chicago, IL / Santa Monica, CA
Tour Type
Guided Group
The road that invented the American road trip. Still delivering.
Route 66 is nostalgia made physical. It is neon signs and classic diners and ghost towns where the highway was rerouted and the place never quite recovered. It is Cadillac Ranch and the Painted Desert and the Santa Monica Pier at the end of 2,210 miles. It does not just look like every road movie you have ever seen — it is where they were filmed.
This centennial edition marks 100 years of the most famous highway in the world. Eight states. One direction. No better time to ride it.
16
Days
2,210
Miles
8
States
100
Years of Route 66
Live Weather Along the Route
Chicago
Live forecast temporarily unavailable
Check forecastAmarillo TX
Live forecast temporarily unavailable
Check forecastFlagstaff AZ
Live forecast temporarily unavailable
Check forecastLos Angeles
Live forecast temporarily unavailable
Check forecastLive data via Open-Meteo. Cached for 10 minutes. Falls back to seasonal guidance when unavailable.
Seasonal Guidance
Temperature Range
5–40°C depending on state | Desert heat in AZ/NM
Best Season
April – October (avoid July–August in desert states)
Watch Out For
Desert heat, Midwest thunderstorms, crosswinds in panhandle, altitude at Flagstaff
Follow the Ride
Andy will be tracking this ride live on Polarsteps — every stop, every mile, every photo.
Live Map Coming Soon
The trip embed will appear here once the Polarsteps trip is created
Tracked via Polarsteps — real-time GPS, photos, and daily diary entries.
Day by Day
Included in the Tour
Guided by EagleRider
EagleRider is the world's largest motorcycle rental and tour company, with over 30 years of experience leading riders across America's greatest roads. This Centennial Tour is their flagship Route 66 experience.
Book via EagleRiderBooking is made directly with EagleRider. The Road Ahead may earn a commission.
Tour Pack Downloads
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View Tour Pack OptionsFrom the 2024 journey — not a brochure
2,400
Miles ridden
14
Ride days
8
States crossed
44°C
Peak Mojave heat
75+
Fuel & food stops logged
Reviews coming in
Riders who've completed a tour can add theirs on the reviews page.
Shot on the ride — no stock, no shortcuts
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Planning your own ride? Explore the complete independent Route 66 motorcycle guide.
Chicago to Santa Monica
16 days. 2,210 miles. 100 years of history. The ultimate American motorcycle journey.