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15 Essential Stops on a U.S. Route 66 Road Trip

Nostalgia and old-time charm run through Route 66, an iconic roadway spanning 2,400 miles from the Midwest to the West Coast. A portion of this legendary highway goes through the Texas Panhandle, although I-40 has replaced Route 66 throughout most of Texas. Many pitstops still keep Route 66 alive. If roadside attractions are what you crave to break up the drive, then this is the road trip to put on your bucket list. The obscure towns and kitschy mom-and-pop shops that appear along the way are perhaps the biggest draws of a Route 66 road trip. This Route 66 Road Trip covers essential stops through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, with everything from farms to forests to deserts along the way.

Pickup Where Your Route 66 Road Trip Begins:

Illinois

Gemini Giant – Wilmington, Illinois Gemini Giant
Credit: Gemini Giant by Larry Myhre

Gemini Giant – Wilmington, Illinois

The original U.S. Route 66 started in Chicago, and that’s where many road trippers choose to start their journeys as well. If you’ve never spent time in the Windy City, some of the top attractions to check out are Navy Pier, the Willis Tower (formerly known as the Sears Tower), the John Hancock 94th floor observation deck, Millennium Park, and the Michigan Avenue shopping district. But then say goodbye to big city life and hit the road, because one of the first random spots stops in Wilmington, Illinois. The Gemini Giant, a large fiberglass 1960s “muffler man,” stands outside the former Launching Pad Drive-In.

Abraham Lincoln's Home – Springfield, Illinois Abraham Lincoln’s Home
Credit: Abraham Lincoln’s Home by cranberries

Abraham Lincoln's Home – Springfield, Illinois

Make sure to stop by Springfield, Ill., to visit the home of America’s president during the Civil War. Abraham Lincoln’s Home is a National Historic Site, and the visitor’s center is opened every day except New Year’s Day, Thanksgiving, and Christmas from 8:30 a.m. to 5:00 p.m. Summer is the busiest time to visit the home, and the site has no entrance fee. There are some other Lincoln-era exhibits and attractions in the neighborhood as well, including Lincoln’s Tomb, the Abraham Lincoln Presidential Museum & Library, and the New Salem State Historic Site.

World's Largest Catsup Bottle – Collinsville, Illinois World’s Largest Catsup Bottle
Credit: World’s Largest Catsup Bottle by Jimmy Emerson, DVM

World's Largest Catsup Bottle – Collinsville, Illinois

If you’re one of those people obsessed with putting catsup on absolutely everything, then a stop at the World’s Largest Catsup Bottle in Collinsville, Ill., is definitely in order. Collinsville is about 12 miles east of St. Louis, Mo., and the catsup bottle is just south of Main Street in downtown Collinsville. Catsup lovers should be sure not to check out the Catsup Bottle Website for some souvenirs, and stay at one of the nearby hotels if you’re starting to feel drowsy.

Missouri

Meramec Caverns – Stanton, Missouri Meramec Caverns corridor near Sullivan MO
Credit: Meramec Caverns corridor near Sullivan MO by Photo 245013850 © Adam Wineke | Dreamstime.com

Meramec Caverns – Stanton, Missouri

Meramec Caverns are located a little over an hour from Missouri’s capital of St. Louis and definitely worth a visit. You honestly can’t miss it along Route 66 if you tried because there are so many billboards advertising it’s coming up along the road! Take a guided underground tour to learn about stalagmites, stalactites, and other rock formations that date back tens of thousands of years. You can also find lodging, camping, zip lining, river boat rides, gold panning activities, and canoeing opportunities nearby as well.

66 Drive-In Theater – Carthage, Missouri

66 Drive-In Theater – Carthage, Missouri

Once upon a time, there were quite a few drive-in theaters along Route 66, but times have changed and many have shut down over the years. However, the 66 Drive-in Theater in Carthage, Mo., is still alive and well! Due to weather and demand, the theater is generally open between April and September of each year. You can expect to see showings of two movies and a classic intermission trailer. The admission price for ages 13 and older is $8, ages 6-12 are $4, and kids under five can watch for free.

Oklahoma

The Blue Whale – Catoosa, Oklahoma The Blue Whale
Credit: The Blue Whale by Chuck Coker

The Blue Whale – Catoosa, Oklahoma

A man named Hugh Davis built The Blue Whale for his wife in Catoosa, Okla., but it quickly became a roadside attraction for locals – extending well beyond family use. The whale was built in the early 70s and is still a favorite local stop. Unfortunately, it’s not still an operational swimming pool for the public, but there’s a picnic area and some great photo opportunities to be had here.

Texas

Conoco Tower Station and U-Drop Inn Cafe - Shamrock, Texas U Drop Inn information office and café
Credit: U Drop Inn information office and café by Photo 194423156 © Brian Scantlebury | Dreamstime.com

Conoco Tower Station and U-Drop Inn Cafe - Shamrock, Texas

Located in East Texas in the small town of Shamrock, the Conoco Tower Station and U-Drop Inn Cafe is a Route 66 landmark. The Conoco Tower Station, which was a popular gas station among travelers along Historic Route 66, was built in 1936 and has been restored to ensure it’s longevity. The Art Deco building is a popular spot to stop and take a picture, since its one of the most beautiful former gas stations around. Connected to the Conoco Tower Station was the popular cafe known as U-Drop Inn Cafe. Sadly, this cafe isn’t an eatery but it is a visitor’s center, gift shop and museum. Both the Conoco Tower Station and U-Drop Inn Cafe have gained even more attention within recent years because it inspired some of the scenes from the Disney movie “Cars.”

The Leaning Water Tower - Groom, Texas

The Leaning Water Tower - Groom, Texas

Don’t simply pass through the small town of Groom, Texas. Groom is home to the Leaning Water Tower, a Texas version of the Leaning Tower of Pisa. The Britten Water Tower was supposed to be used as Groom’s water tank, but this leaning masterpiece didn’t quite meet regulations. Therefore the water tank was purchased by Ralph Britten, purposefully buried in a haphazard way, and now acts as a unique side attraction along Route 66.

Cadillac Ranch – Amarillo, Texas Cadillac Ranch
Credit: Cadillac Ranch by Drriss & Marrionn via Flickr

Cadillac Ranch – Amarillo, Texas

Cadillac Ranch may be one of the most popular Route 66 stops in the Lone Star State. You’ve probably seen car junkyards before, but this isn’t your average automobile graveyard. This unique art display features colorful Cadillacs buried nose down into the Texas earth. Cadillac Ranch has caught the eye of travelers since it was first erected in the 70s. Commissioned as an art piece by millionaire Stanley Marsh III, and these Cadillacs remain partially buried and covered in spray paint graffiti. This “ranch” was built in 1974 and has become one of the must-see attractions in Amarillo. It’s actually visible from the road, but it’s best seen by pulling over and walking through the field to check out the art up-close. You can even add your own graffiti to the art cars. For anyone driving on Route 66 in Texas, this is one photo op you must take.

Amarillo 6th Street District - Amarillo, Texas Amarillo, Texas
Credit: Amarillo, Texas by © Chon Kit Leong | Dreamstime.com

Amarillo 6th Street District - Amarillo, Texas

Amarillo, Texas is the largest Texas town along Route 66. Therefore it’s a great place to spend the night or even spend a couple of days. You will definitely enjoy stretching your legs in the Amarillo 6th Street District. This 13-block district along Route 66 makes for a great photo op, since the architecture is both unique and historic. However also visit the number of art galleries, eateries, and local boutiques in this historic district too.

The Big Texan Steak Ranch - Amarillo, Texas The Big Texan restaurant is a landmark attraction in Amarillo made famous by its location on Route 66
Credit: The Big Texan restaurant is a landmark attraction in Amarillo made famous by its location on Route 66 by ID 74024307 © David Harmantas | Dreamstime.com

The Big Texan Steak Ranch - Amarillo, Texas

If you’ve worked up an appetite on your road trip, stop at The Big Texan Steak Ranch for a hearty steak or home cooked meal. This Amarillo restaurant is a popular Route 66 pitstop not only for its great steaks but also for its steak challenge. If you can devour a 72 oz. steak, along with a serving of shrimp cocktail, baked potato, salad and a roll, within an hour, then you’re meal is free. If you can’t eat the monster meal in time however, you’ll have to pay $72.

Midpoint Cafe - Adrian, Texas Closeup of Midpoint Cafe sign along Route 66
Credit: Closeup of Midpoint Cafe sign along Route 66 by ID 37491550 © Andrey Bayda | Dreamstime.com

Midpoint Cafe - Adrian, Texas

Celebrate the halfway point of Route 66 with a delicious meal at Midpoint Cafe. Located in Adrian, Texas, the Midpoint Cafe is the actual halfway point of the historic road. Basically you’re 1,139 miles from either Santa Monica or Chicago. The Midpoint Cafe is a restaurant, gift shop and antique shop. Built in 1928, the MIdpoint Cafe is one of the oldest running restaurants along Historic Route 66.

Glenrio Historic Site - Glenrio, New Mexico Abandoned service station on Route 66
Credit: Abandoned service station on Route 66 by Photo 34052542 © Sue Smith | Dreamstime.com

Glenrio Historic Site - Glenrio, New Mexico

The last iconic stop in Texas is the Glenrio Historic Site, a place found on the state line of Texas and New Mexico. This ghost town is listed on the National Register of Historic Places. Glenrio is sort of a graveyard of yesteryear. There are no residents or businesses found in Glenrio. However photographers and history buffs alike love seeing the abandoned buildings, antique signs and long-forgotten automobiles found throughout the town.

Arizona

Sitgreaves Pass – Near Oatman, Arizona Sitgreaves Pass
Credit: Sitgreaves Pass by Jasperdo

Sitgreaves Pass – Near Oatman, Arizona

There are many miles of unforgettable scenery along Route 66, but the stretch of road between Kingman and Oatman, Ariz., is one of the best. You’ll see the Black Mountains while making sharp turns, climbing hundreds of feet, and gazing out at expansive views. Oatman itself is a former mining town and there’s plenty of mining history to learn about here in the gift shops and mini-museums.

The Painted Desert, Arizona The Painted Desert
Credit: The Painted Desert by Martin LaBar

The Painted Desert, Arizona

The Painted Desert is just as beautiful as it sounds, with vibrant colors created from the manganese and iron compounds in this natural rock area. There are several places where you can veer off of Route 66 to see scenic state and national parks, but the Painted Desert is the only one that actually contains a portion of Route 66. Petrified wood is plentiful here, and you can even pick up a souvenir of it to take home in the visitor center’s gift shop.

California

Santa Monica Pier – Santa Monica, California Santa Monica Pier
Credit: Santa Monica Pier by Jim Nix

Santa Monica Pier – Santa Monica, California

For many Route 66 travelers, the last stop on the journey is the Santa Monica Pier. This marks the official end of Route 66, with an amusement park, an aquarium, an old-fashioned soda fountain, and lots of restaurants to celebrate the end of your cross-country drive. Make sure to visit the Oatman Rock Shop, which has been around since 1965 and sells lots of shells and souvenirs, as well as the historic carousel and maybe even the onsite trapeze school for something entirely different!