77. The Return of the Road Trip: Route 66 Itinerary
Nostalgia travel is surging as travelers look for authentic, ground-level experiences rather than hurried flights. There is no journey more iconic than the “Mother Road.” Stretching roughly 2,400 miles from Chicago to Santa Monica, Route 66 offers a window into classic Americana, neon signs, and quirky roadside attractions. This guide provides a modern, practical itinerary for navigating this historic highway.
Planning Your Logistics
Before you pack the car, you need to understand the reality of the road today. Route 66 was officially decommissioned in 1985. It does not exist as a single continuous highway on modern maps. Instead, it is a patchwork of frontage roads, state highways, and city streets.
- Time Required: Do not attempt this in less than two weeks. To truly enjoy the stops without driving 10 hours a day, plan for 14 to 21 days.
- Best Season: The sweet spots are May through June or September through October. July and August can be scorching hot, particularly in the Mojave Desert and Texas Panhandle.
- Navigation: GPS often defaults to the fastest interstate route (I-40 or I-55). You will need specific apps like “Route 66 Navigation” or “Roadtrippers” to stay on the historic alignment.
Leg 1: The Midwest Beginning (Illinois & Missouri)
The journey begins in the urban canyons of Chicago. The official start sign is on East Adams Street at South Michigan Avenue.
Chicago, Illinois Start your morning at Lou Mitchell’s. This diner has been serving travelers since 1923 and is known for handing out donut holes and Milk Duds while you wait for a table. It sets the culinary tone for the trip: hearty, classic, and unpretentious.
Wilmington, Illinois About an hour south, look for the Gemini Giant. This is one of the classic “Muffler Men,” a 30-foot fiberglass statue holding a rocket ship. It stands outside the Launching Pad Drive-In and is a mandatory photo op.
St. Louis, Missouri After crossing the Chain of Rocks Bridge (now a pedestrian bridge), you enter Missouri. A visit to the Gateway Arch is standard, but for a true Route 66 treat, stop at Ted Drewes Frozen Custard on Chippewa Street. They have been serving “concretes” (custard so thick you can turn the cup upside down) since 1929.
Meramec Caverns Located near Stanton, Missouri, this cave system is famous for its barn-painted advertisements. It has a rich history as a reported hideout for Jesse James.
Leg 2: The Heartland (Oklahoma & Texas)
Oklahoma contains more drivable miles of the original route than any other state. This section feels the most like the 1950s.
Catoosa, Oklahoma Just northeast of Tulsa lies the Blue Whale of Catoosa. Built in the 1970s as an anniversary gift, this massive concrete whale sits in a pond and remains a beloved, free roadside park.
Arcadia, Oklahoma For a modern twist on the old road, stop at Pops 66. You cannot miss it; there is a 66-foot tall LED soda bottle out front. Inside, you will find a diner and a selection of over 700 types of soda, ranging from classic root beer to bizarre flavors like ranch dressing or buffalo wing soda.
Amarillo, Texas The Texas Panhandle offers wide skies and arguably the most famous art installation on the route: Cadillac Ranch. Ten Cadillacs are buried nose-first in a field west of town. It is public art, and visitors are encouraged to bring spray paint to leave their mark on the cars.
Adrian, Texas You have made it halfway. Stop at the Midpoint Café. There is a line painted on the road across from the café marking the exact equidistant point between Chicago and Los Angeles (1,139 miles to each).
Leg 3: The High Desert (New Mexico & Arizona)
The scenery changes drastically here. The green plains give way to red rocks, mesas, and neon-lit desert towns.
Tucumcari, New Mexico This town is a time capsule. You should book a night at the Blue Swallow Motel. Established in 1939, it features incredibly preserved neon lighting and attached garages for every room. It is widely considered the best-maintained motor court on the entire route.
Petrified Forest National Park, Arizona Route 66 cuts directly through this national park. It is the only national park in the system containing a section of the historic road. You can see the rusted hulk of an old Studebaker marking the alignment.
Winslow, Arizona Thanks to the Eagles’ hit song “Take It Easy,” Winslow is a major stop. Visit Standin’ on the Corner Park, which features a bronze statue of a man with a guitar and a flatbed Ford parked on the street.
Seligman, Arizona This town is the birthplace of the Route 66 preservation movement. Stop at the Snow Cap Drive-In, built by Juan Delgadillo. The menu and the decor are intentionally humorous (look for the “dead chicken” on the door). Juan’s brother, Angel Delgadillo, is often found at the barber shop next door and is a living legend of the road.
Oatman, Arizona The drive to Oatman involves the winding Sitgreaves Pass. In town, wild burros (donkeys) roam the streets freely. They are descendants of miners’ pack animals and expect tourists to feed them hay cubes sold at local shops.
Leg 4: The Pacific End (California)
The final stretch crosses the harsh Mojave Desert before descending into the Los Angeles basin.
Amboy, California Here you will find Roy’s Motel and Café. While the motel rooms are not currently open for guests, the gas station and lobby are. The mid-century modern sign against the empty desert backdrop is one of the most striking visuals of the trip.
Oro Grande, California Visit Elmer’s Bottle Tree Ranch. It is a forest of metal pipes with thousands of colorful glass bottles welded onto them. It sounds like junk, but when the desert wind blows and the sun hits the glass, it creates a unique sensory experience.
Santa Monica, California The route ends at the Pacific Ocean. Drive down Santa Monica Boulevard until you hit the pier. The official “End of the Trail” sign stands on the Santa Monica Pier. Park the car, walk to the end of the pier, and celebrate your arrival at the Pacific.
Frequently Asked Questions
How much does a Route 66 road trip cost? For a two-week trip for two people, budget between $2,500 and $4,000. This includes mid-range motel stays ($80-$120 per night), fuel (approx. $400-$600 depending on your vehicle), food, and attraction fees.
Can I drive Route 66 in a standard car? Yes. You do not need a 4x4 or an SUV. A standard sedan is perfectly fine. However, ensure your spare tire is in good condition and your A/C is working, especially for the desert sections.
Is the road dangerous? Generally, no. The main risks are heat exhaustion in the desert if you break down, or fatigue from long driving days. Some sections, like the Oatman Highway, have tight switchbacks and no guardrails, so drive cautiously.
Do I need to book motels in advance? In peak season (summer), iconic spots like the Blue Swallow Motel in Tucumcari or the Wigwam Motel in Holbrook book up months in advance. For standard chain hotels in larger cities like Oklahoma City or Flagstaff, you can usually book day-of.