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

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Nostalgia and old-time charm run through the veins of Route 66, a legendary highway that spans 2,400 miles from the Midwest to the West Coast. This road trip route passes through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, and you’ll see everything from farms to forests to deserts along the way. But perhaps the biggest draws of this road trip are the obscure towns and kitschy mom-and-pop shops that appear along the way. If roadside attractions are what you crave to break up the drive, then this is THE road trip to put on your bucket list this spring or summer. There are so many amazing stops along Route 66, and here are some of the highlights you’ll see along your journey.

Gemini Giant – Wilmington, Illinois
Gemini Giant

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

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

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.

Meramec Caverns – Stanton, Missouri
Meramec Caverns

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.

The Blue Whale – Catoosa, Oklahoma
The Blue Whale

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.

Cadillac Ranch – Amarillo, Texas
Cadillac Ranch

Cadillac Ranch – Amarillo, Texas

You’ve probably seen car junkyards before, but this isn’t your average automobile graveyard. The Cadillac Ranch was 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.

Sitgreaves Pass – Near Oatman, Arizona
Sitgreaves Pass

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

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.

Santa Monica Pier – Santa Monica, California
Jim Nix
Santa Monica Pier

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!

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