Route 66 was officially decommissioned in 1985, but about 85 percent of the old road is still drivable. Ten days lets you drive it at the pace it was built for. That means time to stop for pie, time to read the faded signs on shuttered gas stations and time to sit outside a motor court at dusk while the neon flickers on. You could rush the 2,400 or so miles from Chicago to Santa Monica in five long days on the interstate. We recommend the opposite: take the old road, take your time and let it show you what America looked like when the drive itself was the vacation.
Best time May or September · Stay 10 days · Budget $$
The route at a glance
Chicago to St. Louis, across Missouri and Oklahoma, the Texas panhandle, New Mexico and Arizona, then down to the Santa Monica Pier. That is eight states, three time zones and a slow change from Midwestern farmland to red rock desert and finally the Pacific. Here is the rough day-by-day plan we followed, with driving times that leave room for wandering:
- Day 1: Chicago to Springfield, Illinois. Start at the “Begin” sign downtown and roll through small towns and cornfields.
- Day 2: Springfield to St. Louis, with a frozen custard stop before crossing the Mississippi.
- Day 3: St. Louis to Joplin, through the Ozark hills of Missouri.
- Day 4: Across the corner of Kansas and into Tulsa, Oklahoma.
- Day 5: Tulsa to Elk City through the long, empty stretches of western Oklahoma.
- Day 6: Into Texas, with a stop in Amarillo and pie in Adrian.
- Day 7: Tucumcari to Albuquerque, New Mexico.
- Day 8: Albuquerque to Holbrook or Winslow, Arizona, with a detour to the Petrified Forest.
- Day 9: Flagstaff to Kingman, including the old road from Seligman.
- Day 10: Through the Mojave to the Santa Monica Pier.
Most days involve four to six hours of actual driving. That sounds like a lot until you realize how often you will pull over. Plan to arrive at your motel by late afternoon so you can walk around town before dinner.
Where the old road is best
Western Oklahoma, the stretch from Seligman to Kingman in Arizona and the desert towns of the Mojave feel almost untouched. In Illinois and Missouri, the old alignment often runs right beside the interstate, and you will hop on and off it constantly. That is fine, and the small towns are charming, but the magic really starts once you pass Oklahoma City.
West of there, the road narrows to two lanes of patched concrete, and the towns get farther apart. Grain elevators stand like lighthouses on the horizon. In the Texas panhandle the sky gets enormous, and by the time you cross into New Mexico, mesas start rising on either side of the car.
The Seligman to Kingman section in Arizona is the longest continuous piece of original Route 66 left, at roughly 160 miles including the loop through the mountains toward Oatman. There are almost no billboards, few other cars and plenty of quirky roadside stops. Fill your tank before you start, because gas stations are few and far between.
The Mojave finale
California’s desert stretch, from Needles toward Barstow, is starkly beautiful and very hot in summer. Some sections of the old road here are rough or periodically closed for repairs, so check current conditions before you go. If a stretch is closed, the interstate runs close by, and you can rejoin the old road a few exits later.
Sleeping on 66
Book at least a few of the restored motor courts, because they are part of the point. Many of these mid-century motels have been lovingly fixed up by new owners who keep the original neon signs, carports and tiled bathrooms while adding comfortable beds and good showers. Rates are usually reasonable, often in the range of $80 to $140 a night, and the owners tend to be full of stories about the road.
On our trip, we split our nights roughly in half: classic motels in towns like Tucumcari, Holbrook and Seligman, and modern chain hotels in bigger cities like St. Louis and Albuquerque where the motor courts are harder to find. That mix kept the budget steady and gave us a few reliable nights of laundry and good Wi-Fi.
May and September are the sweet spots for weather and crowds, but popular motels can still fill up on weekends. Book the ones you most want to stay in a few months ahead, and leave the rest flexible so you can stretch or shorten a day when you find a town you love.
Download offline maps. Cell service disappears for long stretches in Arizona and New Mexico.
Road-trip writer Nora Feld
Eating your way west
Half the fun of Route 66 is the food. Every few hours there is another diner with a long counter, vinyl stools and a waitress who calls everyone “hon.” Order the daily special, ask what pie is fresh and do not count calories for ten days.
In the Midwest, look for frozen custard stands, horseshoe sandwiches in Springfield and fried chicken in small Illinois towns. Oklahoma and Texas lean toward chicken-fried steak and barbecue. Once you hit New Mexico, everything changes: red and green chile appear on almost every menu, and a breakfast burrito smothered in both is the best way to start a long driving day. In Arizona, look for Navajo tacos made on fry bread near the Painted Desert.
Pack a cooler with water, fruit and snacks for the long empty stretches. There are some hours on the road, especially between Kingman and Barstow, where you will not pass anywhere to eat at all.
Don’t miss
Every Route 66 traveler builds a personal list of favorite stops, but a few landmarks belong on everyone’s. These were the ones we would go back for:
- The Gemini Giant in Wilmington, Illinois
- A slice of pie in Adrian, Texas, the midpoint of the route
- Neon at night in Tucumcari
- The end-of-the-trail sign at the Santa Monica Pier
A few extras worth a short detour: the painted Cadillacs half-buried in a field outside Amarillo, the Blue Whale swimming hole near Catoosa, Oklahoma, the Petrified Forest and Painted Desert in Arizona and the wild burros that wander the main street of Oatman. Each one adds an hour or two, and each one is exactly the kind of thing Route 66 was made for.
Practical tips for the road
A few lessons we learned the hard way:
- Use a dedicated Route 66 guidebook or turn-by-turn guide. Phone navigation will constantly try to send you back to the interstate.
- Fill the gas tank whenever it drops below half in the western states.
- Carry cash for small-town diners, souvenir shops and motel deposits.
- Plan for a one-way car rental fee if you are not driving your own car. It can add a few hundred dollars, so compare companies.
- Bring sunscreen and a hat. The desert sun is strong even in May.
Key takeaway: Drive the old road whenever you can, even when the interstate is faster. That is where the stories are.
Ten days on Route 66 is not really about getting from Chicago to Santa Monica. It is about the people behind motel counters and lunch counters, the faded murals on brick walls and the feeling of driving into a sunset with nothing on the schedule but the next small town. When you finally reach the pier and see the end-of-the-trail sign, you will probably feel a little sad that it is over. That is how you know you drove it right.