Route 66 — Chicago to Santa Monica

September 1, 2026Chicago, Illinois → Santa Monica Pier, California0 riders
INTERMEDIATE3940 km

The ultimate American road trip on the Mother Road. From Chicago's Lake Shore Drive to the Santa Monica Pier, Route 66 spans 2,448 miles across eight states through the very heart of America. Pass through the neon-lit streets of St. Louis, the Gateway Arch, the Oklahoma plains, the Texas Panhandle, New Mexico desert, Arizona canyon country and the Mojave Desert before hitting the Pacific Coast. The road is now largely replaced by Interstate 40 but historic sections survive through Illinois, Missouri, New Mexico and Arizona. Plan 10-14 days minimum to do it justice.

Route

Day 1-2: Chicago through Springfield IL Day 3-4: St Louis MO, Cuba MO, Lebanon MO Day 5: Oklahoma City, Route 66 through OK Day 6-7: Texas Panhandle, Amarillo Day 8-9: New Mexico — Santa Fe, Albuquerque Day 10-11: Arizona — Gallup, Flagstaff, Williams Day 12-13: Kingman AZ, Needles CA, Barstow Day 14: San Bernardino, Los Angeles, Santa Monica

Ride Info

DateSeptember 1, 2026
StartChicago, Illinois
EndSanta Monica Pier, California
DifficultyINTERMEDIATE
Distance3940 km
Riders0