The Mother Road. America’s Main Street. Will Rogers Highway. The country’s most iconic thoroughfare has been inspiring road trippers to “get their kicks” since 1926. What better time to plan the ultimate road trip than on the eve of Route 66’s centennial?

A hundred years ago, only around 800 miles of the iconic 2,448-mile-road was paved. The rest of the eight-state-spanning route designed to connect Chicago, Illinois to Santa Monica, California consisted of dirt and gravel. From its role as an essential route for migrants during the Dust Bowl to its road tripping heyday in the 1950s, the blacktop has seen its share of history. 

While Route 66 was officially decommissioned in 1985, you’ll still find plenty of visitors reliving the glory days of the Mother Road — including many from overseas. The lore and nostalgia of the iconic road has etched a permanent place into American pop culture and is celebrated the world over. From desolate desert landscapes to bustling big cities, Route 66 offers a timeless glimpse into the best of Americana.

Ready to hit the road? Here’s everything you need to know to plan your trip.

Planning Your Great American Road Trip

So how long does it take to drive nearly 2,500 miles across eight states? Technically, you’re looking at around 40 hours of highway driving … with no stops. However, getting from point A to point B is hardly the point. There’s a lot to consider before hitting the road, from when to go and how long it will take to how to prep your car for the ride.

How Long Does it Take to Drive Route 66?

While you could easily spend a month exploring every kitschy attraction and major city along the way, you’ll probably want to plan for at least two weeks. The less time you have, the more you’ll need to hop on interstates here and there to bypass occasional traffic and slow speed limits on the historic original route.

When Should you Road Trip on Route 66?

While the summer months are traditionally high season for road trips, consider a few different factors when planning your adventure. First, the prime summer months (July, August) may not be ideal. Not only are you likely to have triple-digit temps to deal with, it’s also monsoon season in the Southwest, which means thunderstorms, flash floods, dust storms and the potential for a whole lot of lightning.
 

The height of winter offers its own set of challenges in the northern states. Chilly temps, snow and icy roads can put a damper on your adventure, and some mountain passes may even be closed. Not only that, you’re also likely to run into reduced hours and even seasonal closures at many of the attractions along Route 66 in the “low season.” 

While there’s really no bad time for a Route 66 road trip, late spring, early summer and early fall are the sweet spots. From mild temps and smaller crowds to roadside wildflowers and stunning fall foliage, these months offer ideal road trip conditions.

Get Ready to Hit the Road 

Before you even think about cranking the engine, you’ll want to make sure your car is ready to roll. This DIY car maintenance checklist is an excellent place to start. From checking your tire pressure to topping off your fluids, follow this list to make sure your ride is safe and ready for Route 66.

Not sure what to pack? We’ve got you covered with this road trip checklist. Think: registration, car insurance, cash, roadside emergency kit, and the like. And don’t forget your roadside assistance information, if you have it. Tip: Your credit card may include access to roadside assistance should you find yourself in a jam.

Now that your bags are packed and your car is ready for the road, there’s only one thing left to do: decide what you want to see! A word to the wise. Historic Route 66 isn’t always easy to follow, so it pays to pick up a map before you hit the road.

While there are many excellent stretches of the historic route with roadside attractions that harken back to a bygone era, at other times the route funnels into a highway — or even an occasional full-stop dead end. Knowing a few landmark attractions you want to see can help you stay on track. Here are 10 iconic stops that are worth pulling over for, from Chicago to the Pacific Coast.

10 Essential Stops on Your Route 66 Road Trip

Route 66 Association of Illinois Hall of Fame and Museum, Pontiac, Illinois

Kick off your adventure (or end it, depending on where you start) soaking up the history of America’s Main Street. Located in quaint downtown Pontiac, the museum is housed in the 1900 Pontiac City Hall and Fire Station building, which is home to a collection of museums. The free museum is chock full of memorabilia and includes an outdoor mural of the Route 66 shield that makes for an excellent first photo op. Tip: Wander around the charming downtown to spot the city’s other 23 murals.

Meramec Caverns, Sullivan, Missouri

As you travel through the Midwest, you’ll no doubt see signs for Meramec Caverns on barns and buildings along Route 66. A popular attraction since 1935, the 4.6-mile limestone cave system formed millions of years ago. Today, you can take a guided walking tour through the magnificent formations to hear stories about how the caves are said to once be a stop on the Underground Railroad — and a hideout for outlaw Jesse James. 

While the tour takes just under an hour and a half, you could easily spend a lot longer at Meramec’s other attractions, which include panning for gold, a zipline and riverboat rides. Just be sure to stop in the candy store for fudge and other road trip treats on your way out.

Blue Whale of Catoosa, Oklahoma

If you’re looking for kitsch, don’t miss this 80-foot-long loveable whale that’s been drawing visitors to his pond since 1972. Created by a retired zoologist as a place for his grandkids to play, the appeal has grown well beyond family over the years. While you can no longer swim in the pond, the Blue Whale is a charming spot to enjoy a picnic lunch — or maybe even do a little fishing.

Cadillac Ranch, Amarillo, Texas

Though it was moved two miles west of its original location in 1997, the sight of 10 Cadillacs buried nose-first in the ground on the side of the highway remains one of America’s most enduring roadside attractions. The public art installation was created in 1974 by The Ant Farm art collective and soon became one of Route 66’s most iconic sights. Today, a social media ready selfie is a must when you’re passing through these parts.  

Midpoint Cafe, Adrian, Texas

You’ve made it to the midpoint of Route 66! What better way to commemorate the moment than with a tasty piece of “ugly crust” pie? This homey diner is big on kitsch, in the best way possible. It’s a fun and friendly place to stop in for a burger, BLT or good old fashioned grilled cheese sandwich. And if you haven’t picked up enough Route 66 souvenirs yet, they’ve got you covered in the gift shop. 

Meteor Crater, Winslow, Arizona

First things first, this 500-foot, nearly mile-wide impact crater is located in Winslow, Arizona. Ring a bell? Cuing up “Take it Easy” by the Eagles is practically a requirement as you roll into town (“Standin’ on a corner in Winslow, Arizona …”) 

Now that we’ve got that taken care of, let’s talk about this massive crater. More than 50,000 years ago, a giant iron-nickel meteorite weighing several hundred thousand tons made impact right here next to Route 66 / I-40 — with a force reportedly 150 times stronger than the atomic bomb. Marvel at the giant crater from an air conditioned viewing area, an outdoor observation deck, a self-guided trail, or a guided tour along the rim.

Fun fact: Back in the ‘60s, several Apollo astronauts trained for their walk on the moon at Arizona’s Meteor Crater. 

Seligman to Kingman, Arizona

The drive along historic Route 66 through Arizona rewards road trippers with retro signage, classic cars, and a heaping dose of Route 66 kitsch backed by a picturesque desert landscape — don’t miss it. From I-40, pick up Old Route 66 in Seligman, then drive through tiny atmospheric desert towns for 83 miles until you hit Kingman. Start off with a burger and a shake at Delgadillo’s Snow Cap drive-in in Seligman, a Mother Road mainstay since 1953. 

Further down the scenic route, you’ll hit Peach Springs, which the fictional town of Radiator Springs is based upon in the movie “Cars.” Peach Springs is also home to the Grand Canyon Caverns, a fun retro stop where you can explore caverns 21 stories below ground. Back on Route 66, Hackberry General Store is another fun stop on the way to Kingman for a snack, a souvenir, and plenty of photo ops in front of old gas pumps, retro signage and rusted out vehicles.

Oatman, Arizona

In Kingman, pick up Oatman Road and buckle your seatbelt for 42 miles of rustic, winding road that takes you through a rocky desert landscape straight out of the Wild West — which is exactly where you’ll arrive when you reach the town of Oatman. The history of this old mining town runs deep, and today you can see daily re-enactments of a gun-spinning shootout on the wooden sidewalks of Main Street. You’ll also see the town’s friendly burros, and lots of them — after all, Oatman is home to more burros than people.

WigWam Motel, San Bernardino, California

What kid hasn’t dreamed of sleeping in a teepee? Perhaps it’s time to make your dream a reality. The WigWam Motel offers guests simple, standalone motel lodgings in one of 19 modern teepees surrounding a small kidney shaped pool. Originally built in 1949, this location was one of seven total outposts. Today, you’ll find one more WigWam still standing along Route 66 in Holbrook, Arizona.

Santa Monica Pier, Santa Monica, California

Once you see the sparkling Pacific Ocean and endless sands of Santa Monica beach, you’ve made it to the terminus of Route 66. You’ll find an excellent photo op at the “End of the Trail” Route 66 sign on the Santa Monica pier. Stick around awhile to ride the ferris wheel and celebrate your accomplishment at an amusement park overlooking the ocean. 

Now that you’ve conquered the ultimate American road trip, where will your travels take you to next? Whether you’re searching for secret swimming holes or chasing fall foliage, keep your ride in PEAK condition so you’re always ready to hit the road.