Riding Route 66 from Chicago to Los Angeles is the kind of trip that reshapes how you think about scale.
Four thousand kilometres of largely two-lane blacktop, old diners, grain silos, and big sky unfold over roughly 35 to 45 days depending on your pace — most riders average 90 to 120 kilometres a day with rest days built in for the inevitable tyre issues and the equally inevitable pie stops.
The road surface is genuinely variable. Stretches through Illinois and Missouri are smooth and well-maintained, but sections of the original alignment in New Mexico and the Mojave can be cracked, buckled, or simply disappear into gravel for short patches. You share the road with traffic throughout — there is no separated cycling infrastructure — so confident road cycling skills matter more than raw fitness.
The iconic corridor through the Ozarks delivers real climbing, and the long desert pulls across Arizona and California carry their own punishment through relentless heat and headwind rather than gradient. Ride west to east in spring if you want the prevailing wind behind you, though most cyclists travel Chicago to LA for the narrative.
Accommodation runs from motels with genuine character (some still fitted out as they were in the 1960s) to basic campgrounds and the odd cyclist hostel. Wild camping is possible across drier states with care. Bike hire along the corridor is sparse and unreliable, so bring your own touring rig or ship one ahead. Water carries become critical from eastern New Mexico onwards — carry three litres minimum between towns.
April through early June and September through October give you manageable temperatures across the full route; summer desert crossings in July and August can be genuinely dangerous.