Route 66 Road Trip Planner

One of the most iconic and famous roads in the world is undoubtedly historic Route 66 which spans across eight states running from Chicago, Illinois to the beaches of Santa Monica, California on the west coast. Established in 1926 and historically one of the most well-traveled highways in America, Route 66 runs for 2,448 miles.

Classically referred to as the “Mother Road” by famous American author John Steinbeck, it runs along farm towns, abandoned cities, spectacular scenery, and tons of quirky stops that simply put, make road trips worth the gas. Route 66 has inspired songs, TV shows, books and more and if it’s inspired you to hit the road and experience a slice of Americana culture for yourself, then here’s everything you need to know to plan the ultimate road trip.

Is Route 66 still worth driving?

Throughout the years the historic Route 66 has been repaved, re-routed, and improved so that there isn’t one definitive Route 66 road to follow, but about 80% of the original route can still be driven today with dozens of stops along the way to make this epic road trip vacation very much worth your time.

Decommissioned in 1985, Route 66 fell to the wayside because of the convenience of the federal interstate system. Designed to get people across state lines faster with fewer exits and slow downs through small towns, today’s interstates diminished tourism to Route 66. However, if you love small towns, unique history, obscure attractions, and supporting local businesses, then a trip down memory lane on historic Route 66 is just what your adventurous heart needs.

How long does it take to drive the whole of Route 66?

It takes about three full weeks to drive the whole of Route 66, closer to four weeks if you take a leisurely pace. Whether you drive your own car, rent an RV or take on the open roads with a motorcycle, you simply can’t go wrong. Traditionally, the route was driven westward from Chicago to Santa Monica as the country expanded, however whichever way you make the journey you can experience the same sightseeing stops. 

What month is best for Route 66?

Since you’ll be driving through several different states, you will experience tons of different temperatures and climates on your road trip. However, to avoid extreme heat or cold, we recommend planning your Route 66 road trip for spring or fall.

Roughly April to June is perfect because it’s not the high summer season that can bring more crowds and higher motel rates along your route. Or wait until after summer from September to October if you want cooler temps without the need to worry about snow or heavy rains. Simply keep in mind that you will be traveling through six climate zones so be prepared for just about anything!

Suggested Route 66 road trip itinerary 

The best thing about a road trip is that you can make it your own and decide where to stop along the way, but here are some must-see spots along Route 66 that we suggest stopping at if you’re making your way across the U.S.

You can use this Google maps route as a guideline for your trip or purchase a Route 66 travel guide book on Amazon to help plan your trip. Below we’ll lay out our top suggestions by state starting in Illinois and ending in California.

Illinois 

Lou Mitchell’s is a good old fashioned diner in Chicago, Illinois and the perfect starting point for your all-American road trip down Route 66. It’s located along the original route created in 1926 and they have classic diner fare to get your road trip started off on the right foot.

Your next stop could be Old Joliet Prison, immortalized by Jack Kerouac who went “by the Joliet pen”, The Blues Brothers, the show Prison Break, and even Bob Dylan. You can explore the eerie grounds and imposing limestone walls. And just another 30 minutes away is the Launching Pad Drive-In where you can snap a pic with a 28-foot Gemini Giant statue.

It’s not necessary, but if you have the time you can drive all the way until you see the Gateway Arch of St. Louis and then make your way through Missouri.

Missouri

Aptly named the Gateway to the West, St. Louis has tons of breweries to visit including the historic Anheuser-Busch brewery that you can tour. After you’ve experienced the city life, make your way out to Meramec Caverns for a guided tour of the stunning stalagmites and stalactites - rumored to be a hideout for the infamous bandit Jesse James.

And of course, a stop for the night at the Wagon Wheel Motel is a must. The cottage built in the 1930s is a landmark and the oldest continuously operated motel on Route 66. It’s been restored but you can take a picture by the original neon sign built in 1947.

Next, visit Fanning 66 Outpost to catch a glimpse of the world's largest rocking chair and stock up on snacks in the truly impressive general store with over 250 glass bottle sodas, 300+ flavors of popcorn, and 75 flavors of fudge. Finally, drop by the 66 Drive-In for a classic outdoor movie.

Oklahoma 

A popular spot for Route 66 roadtrippers to stop in Oklahoma is the Coleman Theater. The historic Spanish Revival theater is a marvel with a variety of gargoyles, dolphins, cherubs and more decorating the vaudeville interior. Next, you can visit the abandoned Chelsea Motel or Totem Pole Park boasting - you guessed it - the world’s largest concrete totem pole!

As you pass through Tulsa, we recommend stopping at Buck’s on 66 for a picture with the giant spaceman, and then Bridge #18 at Rock Creek which is a part of Historic Route 66. And if you’re a fan of bikes, don’t forget to stop by Seaba Station Motorcycle Museum. The former gas station is filled with wall to wall bikes and even a custom motorcycle used in the Captain America film.

Texas

The first pitstop that welcomes travelers to the Lone Star state is Tower Station and U-Drop Inn Cafe. Originally a gas station and diner, it’s now a full visitors center and allegedly has a booth seat where Elvis once ate! More quirky history awaits at the Devil’s Rope and Route 66 Museum - aka the Barbed Wire Museum. Their unique collection of American goods includes the evolution of the cowboy, vintage gas pumps, and the history of ranching.

If you’re up for a food challenge - or simply a good show - stop by The Big Texan Steak Ranch. The hotel and restaurant has the ultimate challenge for tourists, if you can finish the 72 punch steak dinner then your meal is free, or you can simply watch the challengers take on the massive meal as they sit on a stage in the middle of the kitschy western restaurant.

And don’t forget to drop by Cadillac Ranch as you head to New Mexico. This must-see Route 66 landmark is a group of vintage cars buried into the ground covered in graffiti!

New Mexico

If you need a place to stop for the night once you’ve crossed the border, we recommend Blue Swallow Motel, a shrine to Americana culture including an impressive neon sign. As you pass through Albuquerque there are tons of options including the classic 66 Diner where you can enjoy a banana split and snap a selfie in front of the wall of vintage tin signs.

And on your way out of the state, stay a night at the El Rancho Hotel where John Wayne once slept.

Arizona

The first road trip stops in Arizona include the Petrified Forest National Park and the Rainbow Forest Museum. It’s a great place to stretch your legs and marvel at the 225-million-year-old fossils. You can also take a detour to the Grand Canyon’s South Rim, however we suggest walking the rim of the Meteor Crater National Landmark instead for something a little different. It’s the prehistoric footprint of an asteroid that hit the Earth.

And on your way out of the state, we recommend stops in Seligman and at Mr. D'z Route 66 Diner. Seligman is basically the real life version of Disney’s small town Radiator Springs from Cars and the entire town is filled with iconic kitsch and history. Mr. D’s Route 66 Diner is a classic 1950’s diner to fill up for the last leg of your road trip!

California

Funky in all the best ways, you have to explore the glass-bottle forest at Elmer’s Bottle Tree Ranch when you’re passing through the Mojave Desert. If you love antiques and art sculptures, this is the stop for you!

One last iconic Route 66 themed stop in California is the Cucamonga Service Station. Built in 1915 and nationally recognized as a Route 66 landmark, the original building has been restored and it’s now a public museum.

And you’ve officially made it to the end of your journey when you hit the Santa Monica Pier packed with street performers, rides, carnival games, and delicious treats!