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7 Can’t Miss Photo Ops on Missouri’s Route 66

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Taking Missouri's Route 66 road trip in Springfield is a fun place to learn about the iconic highway, plus, there are dozens of photo-ops.

Missouri’s Route 66 is comprised of over 300 miles with picturesque scenery. It is often referred to as The Mother Road, Will Rogers Highway, or the Main Street of America. This beloved slice of Americana continues to bring millions of visitors, both domestic and international, annual to drive the retro highway, initially commissioned in the 1920s. From motels decked out with all sorts of fun neon signs to quirky restaurants and roadside attractions,  Route 66 is sure to convey a sense of nostalgia and fun.

The artsy Red Oak II is one of the cool things you'll see on Missouri's Route 66 road trip.

This spring, I took a road trip through Springfield, Missouri, the “Birthplace of Route 66”. Springfield is a major player in the international business market. It feels sophisticated and trendy though it maintains a significant foothold in the Route 66 nostalgia factor.

Those wanting the ultimate road-trip experience should drop by the Route 66 Springfield Visitor Center for literature and maps about the area’s attractions. This can help in planning your trip or seeing things that you might have missed when researching your travels online. The Visitor Center is also a fun photo-op in itself.

Be sure to have your camera ready for these seven can’t miss photo ops along the way, and by all means, put yourself in the photos as well! 

driving Missouri's Route 66

1. Best Western Route 66 Rail Haven Motel

Enjoy sleeping in the vintage Best Western Route 66 Rail Haven Motel, bursting with whimsical memorabilia. Check in at the traditional motor lodge front desk and receive your key to the Rail Haven Motel rooms and have your complimentary continental breakfast. You can even book the Rail Haven Motel room where Elvis Presley once slept!

Tasteful and comfortable furnishings decorate the clean, modernized rooms of the Rail Haven Motel. Outside is a swimming pool, spa, and a treasure trove of neon and other cool signage. Car enthusiasts, as well as travelers and Route 66 chasers, flock to this popular motel that has been in business for over 75 years.

Tip: Ask for a souvenir card with the original logo. Hold the key card in front of the vintage automobile parked outside for a tremendous Instagram-worthy photo. You may also want a photo underneath Missouri’s Route 66 birthplace sign near the highway, as you see I’ve done below. The vintage cars on the property are also great photo opportunities.

Fun Fact: Missouri’s Route 66 Rail Haven is listed on the National Register of Historic Places.

Best Western Route 66 Rail Haven Motel is one of the cool things you'll see on a classic Missouri Route 66 road trip.

2. Route 66 Museum

The Springfield History Museum on the Square (66 Museum) is a great place to familiarize yourself with how big of a deal road trip travel was after being established on November 11, 1926. The admission price is a mere $5. Things in the museum I enjoyed were the drive-in restaurant menus, gas station attendants uniforms, logbooks from travelers, and very cool signs. Missouri’s Route 66 went right through the Springfield square where the museum is located. To help understand why this road was so important, here is a noteworthy thing I learned at the Route 66 Museum.

In the 1930s and 40s, people were driving for vacation. The journey of the drive WAS the vacation. Because of this, gravel roads became paved, and businesses sprang up to meet the demands of the influx of motorists. Years later, when the interstate came through, many of those businesses closed up since they lost so much traffic.

Tip: Take wicked cool pictures in front of the lovely, neon-clad Route 66 Museum.

Fun Fact: Only steps away is where “Wild Bill” Hickok and Davis K. Tutt had the first one-on-one quick draw duel in 1865. The spot is marked, making it another great historical photo-op.

The Route 66 Museum is one of the cool things you'll see on Missouri's Route 66 road trip.

3.  Boots Court

Completed in the 1940s, the Boots Court lies where Old Route 66 and Highway 71 intersect in Carthage, Missouri. This area is called the “Crossroads of America”. It was a popular place for motorists to stay during the heyday of  family vacations in the 1940s and 50s with an art deco/modern look to it, much different than other existing motor lodges.

Today, Boots Court is recently renovated yet still holds on to the charm and allure of the motel from back in the day. The outside remains almost identical to when it originally opened, with the recognizable black Carrara glass accenting the structure. From the chenille bedspreads to the radios, needlepoint chairs and pillows to monogrammed towels, the Boots Court has done a great job of preserving the past for us all to enjoy. Each room still comes with its own covered carport.

Tip: Visit Boots Court at night for photos of the neon sign in action. Whether you are staying there or not, the owners may still let you see the inside of the rooms, great for classic Missouri’s Route 66 photographs.

Fun Fact: Clark Gable stayed at Boots Court twice.

Boots Court is one of the cool things you'll see on Missouri's Route 66 road trip.

4. Red Oak II

Dubbed an open-air museum in Carthage, Missouri, Red Oak II is a massive complex with houses, art installments, buildings just for touring, and lots of whimsy created by the artist and Carthage resident Lowell Davis. Dubbed the “Norman Rockwell of Rural Art,” Lowell’s collection makes everything photogenic, from the vintage cars to the hand-painted birdhouses. Strolling through the Red Oak II village is a walk through the past, with items salvaged coming to life in a rebirth of incredible art displays.

The artsy Red Oak II is one of the cool things you'll see on a classic Missouri Route 66 road trip.
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Tips: The coolest photo-op is the jail, complete with calaboose and a real jail cell. Another fun structure is the Hooker Tavern from Oklahoma that was moved to Red Oak II while there is also an 1884 schoolhouse, general store, 1920’s Phillips 66 gas station, blacksmith shop, town hall, and diner. Honestly, everything about Red Oak II makes amazing backdrops and exciting shots. 

The artsy Red Oak II is one of the cool things you'll see on Missouri's Route 66 road trip.

5. Gary’s Gay Parita

Gary’s Gay Parita is a spruced up and reworked 1930’s Sinclair Gas station in Ash Grove, Missouri. It features original gas pumps and memorabilia from the height of iconic Route 66’s popularity. The signage alone is enough reason to stop by and have a look while the souvenirs, ice-cold drinks, and snacks are other great offerings. Don’t miss the eclectic vintage car collection and the whimsical postcard selection.

Gary's Gay Parita is one of the cool things you'll see on Missouri's Route 66 road trip.

Tip: Gary’s gas station with dinosaur sign is really a great photo-op, plus it mentions Route 66 in the signage. There are also a plethora of cars and jalopies that scream, “Take my picture!”.

Gary's Gay Parita is one of the cool things you'll see on Missouri's Route 66 road trip.

6. Steak ‘n Shake

The Route 66 Steak ‘n Shake restaurant has been a Springfield tradition since the heyday of Route 66’s popularity. People come to not only enjoy the famous steakburgers, fries, and yummy hand-dipped milkshakes but also to relive the historical times of driving Route 66 that made it famous. Steak ‘n Shake’s diner-like feel and retro look make it a comfortable place to reminisce the good ole days.

The original and retro Steak 'n Shake Restaurant is one of the cool things you'll see on Missouri's Route 66 road trip.
Photo courtesy of Sandra Foyt.

Tip: Steak ‘n Shake is fantastic lit up at night and you can see it from blocks away. This is when you will want to hit this Route 66 location and might as well have dinner while you are there.

Fun Fact: Today, there are 544 Steak ‘n Shake locations, but the one in Springfield has been on the National Register of Historic Places since 2012.

The original and retro Steak 'n Shake Restaurant is one of the cool things you'll see on Missouri's Route 66 road trip.
Photo courtesy of Sandra Foyt.

 7. Route 66 Car Museum

For the ultimate Missouri Route 66 experience, take a look at the vintage vehicles that used to cruise these legendary roads. The best place to do this is at the 20,000 square foot Route 66 Car Museum in Springfield. Here, you will find over 70 cars: some from famous movies, some extremely expensive sports cars, and some that are just plain fun.

Guy Mace, the owner of the Route 66 Car Museum, has been adding to his American and European car collection for years. He finally decided to display them back in 2016.

The Route 66 Car Museum is one of the cool things you'll see on Missouri's Route 66 road trip.

During my Route 66 trip, Guy and his beautiful daughter, Dacy, drove my friends and me along Springfield’s Route 66 in two of their fabulous cars, a 1967 metallic golden beige Austin Healey and Rolls Royce Silver Shadow Sedan. Being driven on Route 66 in a fantastic Rolls Royce was an amazing thing! Later we went to the car museum to see the 70 vehicles on display and learn a bit about them. Allow plenty of time at this stop; you’re going to love it!

Tip: Get a stunning retro photo of yourself in front of one of these timeless classics. Warning, it is hard to choose a favorite ride for your photo-op!

The Route 66 Car Museum is one of the cool things you'll see on Missouri's Route 66 road trip.

Get Your Kicks on Springfield, Missouri’s Route 66

Springfield proved to be a wonderful city for my first Route 66 experiences. I learned so much; the way of life for road-tripping families during the Mother Road’s heyday is fascinating. America was indeed built around these iconic highways. I hope you will have a fantastic time exploring the area and capturing excellent photo opportunities along the way.

You seriously didn’t think I could write about the infamous Route 66 without referring to one of my all-time favorite songs, did you?

The Route 66 Car Museum is one of the awesome things you'll see on Missouri's Route 66 road trip.

Thanks to the Missouri Division of Tourism, NATJA, and the Springfield, MO CVB for hosting my Route 66 trip. As with all of my posts, reviews and opinions are 100% mine and unbiased. To learn more about Missouri, see the Missouri state tourism website

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Gary's Gay Parita is one of the cool things you'll see on Missouri's Route 66 road trip.
The retro Sinclair gas station, or Gary's Gay Parita is one of the cool things you'll see on Missouri's Route 66 road trip.
The artsy Red Oak II is one of the cool things you'll see on a classic Missouri Route 66 road trip.
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Fun street art along Missouri's Route 66 highway.
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Getting our kicks on Missouri's Route 66 trip.
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Missouri's Route 66 highway photo ops
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