Route 66 Leg Two: St. Louis to Tulsa

Haunted motels, caverns, wineries, wax museums, and one very big blue whale

  • 45
  • 08:05
  • 400 mi
  • $36
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Created by robmccauley - July 31st 2021

Next up is St. Louis, Missouri, to Tulsa, Oklahoma, a stretch that some travelers consider the heart of Route 66. It’s where east meets west, linking up the Midwest with the West Coast. Much of this stretch is on I-44, which means lots of exits and county roads, but the scenery is often beautiful. When possible, we’ll point out places where you can hop on and off the original parts of Route 66.

Lewis Cafe
4.5

145 S Main St, St. Clair, MO, US

Lewis Cafe

32mi 00h 34m

Cuba, Missouri, United States

Cuba, Missouri, nicknamed “Route 66 Mural City,” will make you feel as if you’ve traveled back in time. The town was founded in 1857 and named after the island nation just south of Florida. Over the years, Cuba has seen its fair share of famous visitors—including Bette Davis, Amelia Earhart, and President Harry S. Truman—many of whom are featured in the town’s murals.

19 Drive-In
4.0

5853 Hwy. 19, Cuba, MO, US

19 Drive-In

If you need a break from driving and sightseeing, catch a flick at the 19 Drive-In. The classic theater opened in 1955 and is still operating seasonally, between March and October.

2
0mi 00h 01m
Wagon Wheel Motel
3.1

901 E Washington St, Cuba, MO, US

Wagon Wheel Motel

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2

In Cuba you’ll find the iconic Wagon Wheel Motel, a 19-room historic Route 66 motel in operation since 1936. Don’t miss nearby vintage gas stations such as the Old Conoco Service Station and a Phillips 66 station.

3
0mi 00h 02m
Cuba City Jail
3.0

prairie st. & 300 blk. of s. main st., Cuba, MO, US

Cuba City Jail

3

On the southwest corner of Prairie Street and South Main Street, you’ll find a concrete block that served as the town’s jail from 1908 to 1954. Today, the building is furnished with traditional prison furniture, including a wood cot, desk, and stove.

4
0mi 00h 02m
Murals of Cuba, MO
3.7

112 N Filmore St, Cuba, MO, US

Murals of Cuba, MO

4

There are so many Route 66 icons to see and experience while in Cuba, but it’s absolutely essential to take a tour of the famous Route 66 Viva Cuba Murals. Take a journey through the town’s history via 12 outdoor murals. For a more in-depth look, a narrated bus tour departs from the Cuba Visitor Center. A self-guided map is available at cubamomurals.com.

5
0mi 00h 01m
Shellies Route 66 Cafe
4.5

402 E Washington St, Cuba, MO, US

Shellies Route 66 Cafe

5
St. James Winery
4.5

540 State Route B, St. James, MO, US

St. James Winery

6
4mi 00h 06m
World’s (Second) Largest Rocking Chair
4.5

5957 Hwy ZZ, Cuba, MO, US

World’s (Second) Largest Rocking Chair

6

The 40-feet-tall rocking chair in Fanning, Missouri, was once Guinness-certified as the World's Largest Rocker. In 2015, it was bumped down to second place by an even larger chair in Casey, Illinois.

7
8mi 00h 12m

100 S. Jefferson, St. James, MO, US

Old City Hall

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8
10mi 00h 13m
S&T Stonehenge Replica
3.7

State Street, Rolla, MO, US

S&T Stonehenge Replica

8
9
23mi 00h 24m
Uranus Fudge Factory And General Store
4.1
9
10
0mi 00h 00m
The Funk Yard On Route 66
3.9

14400 Highway Z, St. Robert, MO, US

The Funk Yard On Route 66

10
11
35mi 00h 34m
Route 66 Museum
4.0

915 South Jefferson Ave., Lebanon, MO, US

Route 66 Museum

11

The Route 66 Museum is a fun stop where visitors can view a reconstructed retro motel room, a gas station, and a diner. Admission is free, but donations are welcome.

12
11mi 00h 12m
Redmon's Candy Factory
4.2

330 W Pine St, Phillipsburg, MO, US

Redmon's Candy Factory

12

If you need a sugar fix, stop in at Redmon’s Candy Factory in Phillipsburg. They make more than 20 flavors of fudge and 70 flavors of taffy in the on-site candy kitchen.

Starlite Lanes
3.9

1331 Historic U.S. 66, Lebanon, MO, US

Starlite Lanes

13
12mi 00h 13m

135 Wrinkle Ave, Lebanon, MO, US

The Vintage Cowgirl at Wrink's Market

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14
0mi 00h 00m
Munger Moss Motel
4.4

1336 E Route 66, Lebanon, MO, US

Munger Moss Motel

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14
15
31mi 00h 31m
Hubble Telescope Replica Statue
4.3

100 S. Clay St., Marshfield, MO, US

Hubble Telescope Replica Statue

15

Edwin Powell Hubble was born in Marshfield in 1889. To commemorate the famous astronomer, there’s a Hubble Telescope Replica Statue on the west side of the town square. It weighs a whopping 1,200 pounds and is one-quarter the size of the actual Hubble Space Telescope. The town itself is cute, too, so if you have time, spend a day strolling around.

16
25mi 00h 30m
Pythian Castle
3.9

1451 East Pythian Street, Springfield, MO, US

Pythian Castle

16

Pythian Castle is frequently listed as one of the best kept secrets in Missouri. Built in 1913 by the mysterious Knights of Pythias, the castle was ultimately purchased by the U.S. military and even housed some POWs during World War II. Today, it’s privately owned and used for historic tours, ghost hunts, escape room events, and murder mysteries.

Ending this leg at the Blue Whale makes for a Route 66 highlight, but you’ve still got plenty of attractions—and more than half of the Mother Road—ahead of you. No longer the road of desperation as described by John Steinbeck in The Grapes of Wrath, you’ll nonetheless be following in the footsteps (or rather, wheel ruts) of thousands of Okies who once traveled West along Route 66 in search of greener pastures. There are more driveable portions of the old Mother Road in Oklahoma than in any other state, so get comfortable and don’t forget to stick your hand (or head) out the window to enjoy the wind as it comes sweeping down the plain.

Banner Photo Credit: Flickr/Nicolas Henderson