Best Things to Do from Springfield to St. Louis, MO on Route 66

Today we begin at Springfield to St. Louis. There’s little to finish on Route 66! We’ve traveled at least 1,600 miles (probably more), and we still have 512 miles ahead to get to Chicago (counting with today).

The day after tomorrow, we will be entering Chicago. We are in the state of Missouri, and we have to go further north to reach the state of Illinois.

From Chicago to St Louis on Route 66

If you want to go from Chicago, IL, to St Louis, MO, you have around 300 miles. But, there are plenty of things to do and visit, so I recommend splitting this day into 2 or 3 if you have enough time.

Here you have how we did these stretches:

Route 66 From Springfield to St. Louis, MO

Historic Route 66 Missouri sign

Route 66 from Springfield to Marshfield

We begin our route in Springfield, where we’ve spent the night today. If you couldn’t see Springfield yesterday, you can do it in the morning, after a good breakfast.

Here, I’ll tell you everything you have to visit in Springfield, Missouri, the Birthplace of Route 66.

If you want to go down Route 66 from Springfield, you must go east to E Kearny Street. This street continues on Route 66, which runs parallel to I-44.

We are going toward a village called Strafford. Once you cross Strafford, Route 66 almost merges with I-44, so you have to be aware to continue parallel to I-44 and not on I-44.


The first stop today is Marshfield. Here, you can visit:

  • the Walnut Springs Farm,
  • the Skyline Cafe
  • Marshfield Oil Co. Station from 1920
  • Route 66 park
  • Marshfield Route 66 Mural
  • Hubble Telescope Replica
  • Missouri Walk of Fame

Hubble Telescope in Marshfield

In Marshfield, there’s a replica of the Hubble telescope. It’s in Webster County Courthouse 140 S. Clay St.

It’s not something unique but for curiosity, worth a stop.

Route 66 from Springfield to St Louis

Indications from Marshfield to Phillipsburg and Lebanon

Once you return from Walnut Springs, you can take from Marshfield again Route 66 (from Washington St at the right side and Hubble Drive W).

Continue driving along with it quite separated from the I-44, in fact, until you get to Conway.

In Conway, Route 66 ends, and you’re forced to merge onto I-44 until Phillipsburg.

In Phillipsburg, you get off the I-44 and pass under it. Route 66 runs parallel to I-44 and has two directions by the left of the I-44 as you go to St. Louis, and you can continue up to Lebanon.

*Note: this indication may change with time. Be sure to have an updated map 🙂


This small town in the Ozarks has some things to visit. So, you may want to stop here.

  • Harris’ Station and Cabins (along Route 66)
  • Harris’ Cafe and Texaco Station
  • Route 66 Commemorative Rest Area (an interesting modern area)
  • Ghost Sign
  • Conway Service Station


Phillipsburg is a small town close to Route 66 with some vintage cafes and gas stations you must visit.

  • Carter & Lawson’s Underpass Cafe and Service Station
  • Timber Hill Station
  • Stan Adams filling station (north of town)
  • Hi-Lite Cabin Court
  • Twin Oaks cabins and Texaco
  • the former Midway Cafe and Standard Station
  • Old Phillipsburg General Store
  • Redmon’s Candy store
  • Historic Route 66 Roadside Park

What to visit in Lebanon?

Lebanon is already a larger town with many places to visit and attractions: including classic US 66 motels, shops, service stations, neon signs, diners, and restaurants.

The Munger Moss Motel is a classic on the road with a good collection of toy trucks.

It was a sandwich shop and opened first in the Devil’s Elbow around 1940 (we will see later) and was moved to Lebanon in 1946 with the highway’s modification.

Taking advantage of the move, it was turned into a Motel and was acquired in 1971 by Bob and Ramona Lehman, known for their passion for Route 66.

bridge from Springfield to St Louis

Also, check Wink’s Food Market. It opened around 1955 and operated for 50 years until its owner died in 2005. It was left abandoned and half-destroyed until his son reopened it in 2007.

It became somewhat famous when Paul Harvey recommended his bologna sandwich for 99 cents. It is curious for a stop on a classic of the route.

From Lebanon to Waynesville

We keep driving! We leave Lebanon and point to a section with many things to see. You can continue on Route 66 in E Seminole Avenue, taking it straight (right where the Munger Moss is), and Route 66 runs parallel to I-44 on your left side as you drive.

Attention! When you find an intersection with some signs that say “Sleeper United Methodist Church,” tour to your right to go over I-44 and continue on route! It’s not indicated, and you’ll be going the wrong way if you don’t.

*Note: this indication may change with time.


In this small town, you’ll find some Route 66 attractions like an Old Phillips 66 Station, Lentz’s Oasis motel and station, and the Gasconade River Bridge from 1924.

If you continue Route 66 to East, you’ll find Clicks Route 66 General Store and Gascozark Store an antique store

Hazelgreen’s Bridge

We arrive at Hazelgreen. And what’s in Hazelgreen? Well, the Gasconade River Bridge, a typical Route 66 bridge, allows passing over the Gasconade River. The peculiarity of this bridge is that it is equal to the Devil’s Elbow Bridge.

Route 66 is separated significantly from the I-44 and is fully immersed in the forests of Fort Leonard Wood, which was the first training camp of the American army. It is 100% operational and is visitable, especially in military museums.

I personally didn’t get too much interest, so I didn’t go, but I leave it here if you’re interested.

Waynesville and the Devil’s Elbow

Waynesville is a small town in the Ozarks region. It has some historic landmarks and US66 Classics.

  • Frog Rock
  • Bell Hotel
  • Bell’s Cafe & Sinclair gas station
  • Rigsby Standard Station
  • Bohannon CafĂ© Garage
  • Mallow’s Market (Owl Cafe)
  • Roubidoux Bridge
  • First S &G motel

On your way from Waynesville to Devil’s Elbow, you’ll find many interesting places to stop on this fabulous road trip on Route 66.

As you get out of Waynesville to your left and up in a landfill is The Frog Rock, a stone that apparently looks like a frog, often painted so that the resemblance is more significant.

Just after The Frog Rock, you drive under I-44, but Route 66 continues parallel to the highway, sometimes closer and sometimes further.

And you will see that something happens, and Route 66 has two lanes for a few kilometers! This is part of its original design! Meanwhile, you may have noticed that the landscape is much greener!

Around St Roberts (and before Devils Elbow) you can visit:

  • Retro Route 66 Diner
  • Old 1950s gas station
  • Rock Face Phillips 66
  • WWII Fort Leonard Wood
  • Uranus Missouri and its Muffler Man, Mega Mayor
Ruta 66 tramo springfield st louis

Devil’s Elbow

Devil’s Elbow is a small village listed as a Historic Place on the US National Register.

Here, you can visit:

  • the Devil’s Elbow Bridge,
  • the Elbow cafe,
  • Devil’s Elbow Cut scenic overlook, and more.

Why is it Called the Devil’s Elbow?

It is called Devil’s Elbow because it is a tight bend where the ships carrying the river logs jammed.

You are about to cross the Big Piney River Bridge and Devil’s Elbow.

As you cross the bridge, you can get closer if you take a small road to the right and run close to the river. A good place to relax for a few minutes.

As you continue on Route 66, you will go through what they call the “Hooker Cut.”

Basically, it’s a point where they had to dig the surrounding mountain so Route 66 could pass through. Of course, nowadays, we are used to seeing it, but it was exceptional work for those times.

From Waynesville to St. Louis

On your way to St. Louis, you’ll cross some little towns and many attractions. Here we are listing some of them.


Arlington is a ghost town on US66. On your way to this town, you can visit:

  • Larry Baggett’s Trail of Tears Memorial
  • Stony Dell Resort – Route 66

You’ll pass Arlington. At the east is the Trail of Tears. A little further, you can go see “The Johns Modern Cabins,” if still standing.

There are some cabins in the woods that, despite the name, aren’t modern and half-destroyed or at least were. I don’t know if they have been restored since 2010.


At Jerome, you can visit the Ruins of an Ozark Resort. A classic attraction from the golden days of Route 66.

What to See in Rolla?

Rolla has many attractions to see, so you have to stop by!

In Rolla, you have a replica of Stonehenge but half the original size inside the university. At least curious.

Also, Rolla, is one of the roads that take you to Mark Twain National Forest if you want to visit.

  • Totem Pole Antiques Trading Post
  • Former Phillips 66 station

Visit St. James

St. James was one of the destinations of the Italians who emigrated to America. They began planting vineyards in that area, and today it produces wines of the recognized name.

You can find a kind of shop at the roadside where you can taste it if you want, but beware! You know, if you drink, don’t drive!

Also, you can visit old gas stations and motels.

Visit Cuba, the Mural City, on Route 66

Cuba, also known as the Mural City, is full of churches, and many attractions on Route 66, and also there is the Wagon Wheel Motel.

It is pretty well preserved and offers visitors the possibility of experimenting with how the old hosting service was. Of course, it has a typical neon sign of Route 66. Go to the Visitor Center for a map, updated info, and some souvenirs.

The majority of the murals are around West Washington Boulevard and Buchanan Street.

  • Harry Truman
  • Prosperity Corner
  • The Millworks
  • A day in the Cooperage
  • The Apple Mural
  • People Bank’s
  • Meeting in Missouri
  • Civil War Murals
  • Gold Star Boys
  • Amelia Earhart
  • History at the 4-Way
  • The River
  • Al West Mural
  • Bette Davis

What to Visit in Sullivan?

Route 66 continues parallel to I-44 to Sullivan; this city is on the old Route 66 alignment, you can find some attractions and it’s also, the hometown of George Hearst, Senator and newspaper magnate.

He is Patty Hearst’s grandfather who kidnapped and took the international press breathless in the ’70s. Patty Hearst suffered an extreme case of Stockholm Syndrome.

She even robbed a bank with her captors. Finally, she was captured and sentenced.

Route 66 Attractions in Sullivan

Meramec Caves in Stanton

Just after Sullivan is Stanton, where you can find Meramec Caves open since 1930 and a highly recommended visit.

Also, the Jesse James Wax Museum and the Ozark Court are old motels with a characteristic neon sign. The sign is no longer there, and the motel maybe not.

Some of Stanton Motels

  • Ozark Court Motel
  • Delta Motel
  • Kovac’s Cafe and Motel
  • Cavern City Hideout Motel and Restaurant
  • the Stanton Motel
  • El Rancho Motel 
  • Benson’s Modern Cabins

Gray Summit

From here, Route 66 and I-44 run almost parallel. Once you get to Gray Summit, you can stop to see the botanical garden, Shaw Arboretum.

On your way to St. Louis, you’ll find more small towns and attractions on Route 66.

meramec caverns on route 66

St. Louis, MO

The vibrant city of St. Louis has many star attractions, including the Gateway Arch and Busch Stadium.

Beyond that, you’ll find that the city has plenty to offer, including great beer, delicious food, sports, and music.

This slice of mid-western Americana will have you charmed in no time. St. Louis is ranked 7th in the country for the Best Weekend Getaways in the midwest.

Gateway Arch St louis sunset

Take a hint from Lewis and Clark and start your exploration of St. Louis! Use this guide to St. Louis to decide what amazing attractions are perfect for you.

In St. Louis, you cannot miss the Chain of Rock Bridge. It was built in 1929 and was originally a toll bridge. Then it supported traffic on Route 66 over the Mississippi River!!

This allowed avoiding crossing the entire city by migrants who did Route 66 and therefore reduce traffic congestion.

This worked from 1937 to 1967. At that time, it was closed to traffic, and its destiny was uncertain until 1990.

In 1990 it was saved from demolition and turned into a pedestrian path. It is characteristic because the middle of the bridge has an angle of 22°, allowing it to resist the river current and easier transit vessels.

And for today is enough. Don’t you think? Use your remaining time to get to know St. Louis and walk around this vibrant city.

And if you find something interesting, do not hesitate to tell us, and we’ll include it immediately!

“Travel is fatal to prejudice, bigotry, and narrow-mindedness.” – Mark Twain.

Route 66 Itinerary + Travel Tips

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Last Updated on 16 September, 2022 by Veronica

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