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The best road trips along Route 66 — America's most iconic highway, ranked

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

Credit: Anatolii Grytsenko  / Pexels

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.

Each entry covers a specific run of the highway rather than a whole state, since state lines rarely line up with where the driving gets interesting. Oklahoma alone holds more drivable Route 66 than any other state. Kansas, by contrast, crosses the road in about 15 minutes flat. Both make this list, for very different reasons. What follows works as a full itinerary read start to finish. It also works as 10 separate answers to the same question: which part of Route 66 is worth the time.

Seligman, Arizona is the birthplace of the Route 66 revival

Credit: Karina G / Unsplash 

No town did more to save Route 66 from disappearing than Seligman, Arizona. It remains the best single stop on the highway for anyone who wants to understand why the road still exists. Interstate 40 opened around the town on September 22, 1978, and traffic through Seligman stopped overnight. A local barber named Angel Delgadillo watched his customers disappear. Rather than close up, he spent the following years lobbying the state to designate the old highway as a historic route. In 1987 he founded the Historic Route 66 Association of Arizona, the first group of its kind. Every state association that followed took its cue from what happened here.

The town now bills itself as the birthplace of historic Route 66, and it earns the title on sight. Delgadillo's barbershop, converted into a museum after his retirement, sits inside the gift shop his family still runs. A few doors down, Delgadillo's Snow Cap Drive-In still serves burgers and a running list of deadpan jokes at the register. Angel's brother Juan opened it in 1953. The Copper Cart, the Roadkill Cafe, and a string of gift shops selling license plates and neon signage line a short main street. Little about it has changed since the 1950s.

Seligman also sits at the start of one of the longest unbroken original alignments of Route 66 anywhere on the route. The 84-mile run west to Kingman passes through the small town of Peach Springs. Drivers heading that direction can stay on the pre-interstate pavement almost the entire way, which is not possible through most other states. The town's whole identity runs through Route 66 rather than any other industry. It feels less like a museum piece and more like a place still making its living off the road it saved. That is the case for putting it first on this list. Much of what still functions as a roadside attraction anywhere on Route 66 owes something to what started here.

Chicago's Route 66 start now runs through Navy Pier to St. Louis

Credit: Wikimedia Commons CC BY-SA 4.0

Chicago moved the official starting point of Route 66 this year, redesignating Navy Pier as the highway's eastern terminus. For nearly a century, the route had started at Michigan Avenue and Adams Street downtown. The city council passed the change to mark the road's 100th anniversary. A new sign went up at the pier during a dedication held on March 25, 2026. The original marker at Adams Street still stands for drivers who want to trace the historic alignment exactly. That route runs south down Jackson Boulevard, then onto Ogden Avenue, through Cicero, Berwyn, and Joliet on the way out of the city.

South of Chicago, Illinois carries some of the best-preserved small-town Route 66 anywhere on the route. Wilmington still has the Gemini Giant, a 28-foot fiberglass spaceman holding a rocket outside a former drive-in. It is one of dozens of oversized statues collectively known as Muffler Men. Pontiac is home to the Route 66 Hall of Fame and Museum, which inducts new names each year and keeps memorabilia from every state the highway crosses. Springfield, the state capital, claims the Cozy Dog Drive In. The Waldmire family began selling a hot dog dipped in cornmeal batter and fried on a stick there in........

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