Free daily briefing on global business news.
A stretch-by-stretch guide to the best Route 66 road trip segments across eight states, from Chicago's Navy Pier to the Santa Monica Pier
Route 66 turns 100 in 2026. The anniversary has done more for the road than any single event since it was decommissioned in 1985. Chicago renamed Navy Pier as the highway's eastern starting point this year. States have restored bridges and signage ahead of the milestone. Towns that emptied out after the interstate arrived have leaned harder than ever into the traffic the old road still pulls in. The original 2,448 miles between Chicago and Santa Monica were never meant to survive intact. Most of it has, in pieces. Figuring out which pieces are worth a detour is the real work of planning a Route 66 road trip.
A full end-to-end drive takes about 10 days at a fast pace, and closer to three weeks done properly with stops. Few travelers have that kind of time. Not every stretch of the highway rewards the extra miles equally, either. Some sections still run on the original 1926 alignment, through towns built entirely around the road. Others have been swallowed by the interstate that replaced them, leaving little more than a frontage road and a faded sign. The ranking below sorts through both kinds. It orders 10 stretches by how much of the real Route 66 experience survives on each one: the neon, the roadside oddities, the diners that predate the interstate system entirely.
