Route 66 Leg Two: St. Louis to Tulsa

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

  • 61
  • 18:31
  • 876 mi
  • $141
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Created by Jacksonator01 - July 19th 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.

8850 Morse Mill Spur Road, Morse Mill, MO, US

Morse Mill Hotel

Twenty miles southeast of Saint Clair, you’ll find the Morse Mill Hotel, an alleged vortex of paranormal activity. This pre-Civil War hotel was constructed in 1816 as a simple farmhouse. Forty years later, John Morse turned it into a four-story building made of maple, oak, cypress, and limestone. During the 1920s and ‘30s, the hotel was buzzing with activity as the place where the wealthy citizens of Saint Louis escaped for a weekend getaway. Famous—and infamous—guests came from all over the world and included Charles Lindbergh and Al Capone. Today, guests report hearing phantom footsteps and feeling apparitions brush up against them.

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32mi 00h 43m

1135 Hwy W, Sullivan, MO, US

Meramec Caverns

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If you’re traveling during the summer months, this nice, cool detour will help you escape the heat. The 4.6-mile-long cave system is one of the Ozarks’ coolest (literally and figuratively) natural wonders, as well as an archaeological hotbed of Native American artifacts.

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3mi 00h 06m

I-44 - Exit 230, Sullivan, MO, US

Jesse James Wax Museum

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The Jesse James Wax Museum in Stanton is an interactive walking museum that takes visitors through the life and mysterious death of the notorious outlaw. The gift shop is loaded with kitschy James memorabilia. The nearby Riverside Wildlife Center, full of snakes and alligators, is also worth a visit.

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36mi 00h 34m
Photo of Route 66 State Park
4.5

97 North Outer Road (Visitor Center & Museum), Eureka, MO, US

Route 66 State Park

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13mi 00h 15m
Photo of Shaw Nature Reserve
4.5

Hwy 100 & I 44 Po Box 38, Gray Summit, MO, US

Shaw Nature Reserve

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14mi 00h 17m

145 S Main St, MO, US

Lewis Cafe

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26mi 00h 32m

17352 Manchester Rd, Wildwood, MO, US

Big Chief Roadhouse

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58mi 01h 01m
Photo of Onondaga Cave State Park
4.5

7556 Highway H, Leasburg, MO, US

Onondaga Cave State Park

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Onondaga Cave State Park is less famous—and less crowded—than Meramec Caverns, but equally impressive. Massive stalagmites and stalactites drip from the ceiling and rise up from the floor, and guided tours take visitors throughout the underground labyrinth. Don’t miss the panoramic vista points where you can see views of the Meramec River.

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7mi 00h 10m
Photo of Belmont Vineyards & Winery
4.5

Old Highway 66, Leasburg, MO, US

Belmont Vineyards & Winery

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Enjoy a wine tasting at Belmont Vineyards, about 8 miles down the road from Onondaga Cave State Park. This family-run business is a hidden gem in the Ozarks, located between downtown Cuba and Leasburg along historic Route 66 (an easy on-off from I-44). Belmont frequently features live music on weekends, and visitors can enjoy wine tastings and good food with a beautiful view.

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7mi 00h 10m

Cuba, Missouri, United States

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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.

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1mi 00h 03m

5853 Hwy. 19, Cuba, MO, US

19 Drive-In

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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.

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1mi 00h 04m
Photo of Wagon Wheel Motel
3.5

901 E Washington St, Cuba, MO, US

Wagon Wheel Motel

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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.

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0mi 00h 02m
Photo of Cuba City Jail
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prairie st. & 300 blk. of s. main st., Cuba, MO, US

Cuba City Jail

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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.

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0mi 00h 02m
Photo of Murals of Cuba, MO
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112 N Filmore St, Cuba, MO, US

Murals of Cuba, MO

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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.

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0mi 00h 02m

913 E Washington St, Cuba, MO, US

Missouri Hick Barbeque

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0mi 00h 01m

402 E Washington St, Cuba, MO, US

Shellies Route 66 Cafe

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11mi 00h 16m

1942 Hwy T, Steelville, MO, US

Peaceful Bend Winery

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17mi 00h 24m

540 State Rt B, MO, US

St. James Winery

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9mi 00h 11m
Photo of World’s (Second) Largest Rocking Chair
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5957 Hwy ZZ, Cuba, MO, US

World’s (Second) Largest Rocking Chair

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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.

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47mi 00h 47m

301 Route 66 East, Waynesville, MO, US

Old Pulaski County Courthouse Museum

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In Waynesville you’ll find the Pulaski County Courthouse, a beautiful two-story Romanesque Revival-style building built in 1903. Today, the courthouse serves as a museum, and is a favorite photo op for history and architecture buffs.

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