Route 66 Leg Two: St. Louis to Tulsa

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

  • 60
  • 18:19
  • 870 mi
  • $126
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Created by Jacksonator01 - July 18th 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.

Morse Mill Hotel
3.0

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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29mi 00h 37m
Jesse James Wax Museum
3.3

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
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
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
Lewis Cafe
4.5

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

Lewis Cafe

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26mi 00h 32m
Big Chief Roadhouse
4.0

17352 Manchester Rd., Wildwood, MO, US

Big Chief Roadhouse

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58mi 01h 01m
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
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.

7mi 00h 10m

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.

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1mi 00h 03m
19 Drive-In
4.0

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
Wagon Wheel Motel
3.1

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
Cuba City Jail
3.0

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
Murals of Cuba, MO
3.7

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
Missouri Hick Barbeque
4.5

913 E Washington St, Cuba, MO, US

Missouri Hick Barbeque

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0mi 00h 01m
Shellies Route 66 Cafe
4.5

402 E Washington St, Cuba, MO, US

Shellies Route 66 Cafe

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11mi 00h 16m
Peaceful Bend Winery
4.5

1942 State Highway T, Steelville, MO, US

Peaceful Bend Winery

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17mi 00h 24m
St. James Winery
4.5

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

St. James Winery

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9mi 00h 11m
World’s (Second) Largest Rocking Chair
4.5

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
Old Pulaski County Courthouse Museum
4.4

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.

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46mi 00h 54m
Ha Ha Tonka State Park
5.0

1491 State Road D, Camdenton, MO, US

Ha Ha Tonka State Park

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You may not expect to stumble upon the abandoned ruins of a castle in the middle of the Ozarks, but when driving down Route 66, this amazing state park is well worth the detour. Tucked behind lush forests and bordered by a vast lake, Ha Ha Tonka State Park is a world unto itself. The name “Ha Ha Tonka” reportedly comes from a Native American phrase for “laughing waters,” a reference to the area’s many springs. There are 17 miles of trails that feature sinkholes, natural bridges, caves, a spring, and the ruins of an early-20th-century castle.

Robert McClure Snyder was born into a family of millers and grocers in 1852. Snyder moved to St. Louis to work in the grocery business and, in 1904, he bought 5,000 acres of land around Ha Ha Tonka Lake and Spring. He started building roads, exploring the caves, and visited the area whenever he needed to escape his busy city life.

Snyder employed Scottish stonemasons to build his dream home, a massive, European-style castle, with an incredible view overlooking the Lake of the Ozarks. Snyder died in 1906, before his dream home was completed, when he became one of Missouri’s first automobile fatalities. In Snyder’s obituary, the Kansas City Journal wrote that he “was a man who understood big things and made them win by keeping up the fight when other men might have been ready to give it up.”

His sons took over construction of the castle and completed it in the 1920s. The castle was used as a residence for most of the next two decades until it became a boutique hotel in 1937. In 1942, a fire completely destroyed the interior and carriage house.

Ha Ha Tonka became an official state park in 1978, and visitors to the stabilized castle can still enjoy the artistic masonry of the ruins.

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