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.
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.
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.
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.
Key West, Florida, United States
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.
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.
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.
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.
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.
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.
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.
Springfield, Missouri, United States
Springfield is known both as the "Queen City of the Ozarks" and the "Birthplace of Route 66." Located in south-central Missouri at a strategic crossroads, Springfield was a railroad hub, home to a bloody Civil War battle, and played an important role in the birth of the Mother Road. Route 66 was aligned through the city in 1926, realigned in 1936, and funneled travelers to the many motels and businesses located along the way until I-44 bypassed the city in 1958.
If you need a break from driving, pull over at the Fantastic Caverns in Springfield and explore an underground world. North America's only completely ride-through cave tour is absolutely worth the 55-minute tram ride.
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.
Don’t miss the Best Western Route 66 Rail Haven hotel in Springfield. This classic roadside hotel has been a Mother Road fixture since 1938. There are several great photo ops around the hotel, including an old-school fire truck and vintage gas pumps. One of the hotel’s claims to fame is that Elvis Presley stayed here, and if it’s good enough for The King, it’s good enough for all of us.
The Precious Moments Chapel in Carthage, often compared to Michelangelo’s Sistine Chapel in Rome, is the lovechild of artist Samuel Butcher. Free tours are offered every day. The gift shop is considered to be the world’s largest Precious Moments gift shop.
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
