One Of Missouri's Most Picturesque Cities Is A Charming Route 66 Gem With Nostalgia And Majestic Caves

Stretching more than 2,400 miles from Chicago to California, Route 66 delivers neon nostalgia and kitschy Americana across eight different states. If you're traveling from east to west, one of the first states you'll pass through is Missouri, which boasts everything from underrated idyllic charmers like St. James to illustrious cities with iconic landmarks such as St. Louis.

Tucked comfortably between St. Louis and Springfield, Sullivan is one of the Show-Me State's most picturesque little cities that's worthy of a prolonged pit stop along the endearingly nicknamed Mother Road. Home to retro roadside motels and nostalgia-inspired murals, the town offers plenty of Route 66 attractions and an array of nearby gems within easy driving distance. Perhaps the most sparkling of these is Meramec State Park, a natural wonderland of hardwood forests, riverside beauty, and majestic caves to explore. If you're rolling along Route 66, make it a point to stop and stretch your legs in Sullivan.

If you're embarking on a stunning and storied road trip across America along Route 66, Sullivan is easy to reach by car via Interstate 44, which runs directly through the heart of town. With a population of just over 6,000 residents, Sullivan exudes a small-town atmosphere brimming with historic charm. Founded in 1856, the town beckoned settlers to the area with the crystalline waters of the Meramec River and the abundant landscapes surrounding it.

In 1926, the original alignment of Route 66 was built, cutting directly through Sullivan. To accommodate the influx of long-distance travelers cruising down the Mother Road, classic roadside motels began popping up throughout the town during the mid-20th century. Though many were ultimately abandoned and demolished, the Shamrock Court Motel still stands, dazzling nostalgia seekers with its retro neon sign and Ozark-style architecture. If you want to book a stay, you'll have to wait for a bit. Built in the late 1940s, the iconic Route 66 motel flourished as a roadside lodge until the construction of I-44 diverted traffic away. It was later converted into efficiency apartments in the early 1970s. As of this writing, the motel is undergoing a major restoration and plans to reopen to short-term travelers in 2026 –- just in time for the 100th birthday of Route 66.

While you're in town, be sure to peep the Route 66 murals. The most prominent, at 227 E. Springfield, features a 1950s jukebox, a diner waitress, and a classic automobile cruising down the historic highway. Also keep an eye for the town's fire hydrants -– 27 of them are painted with recognizable Route 66 cities and landmarks, from the "Begin Route 66" sign in Chicago, to the "End of the Trail" sign in Santa Monica.

After exploring the Route 66 sites around town, a journey to Meramec State Park is a must. Located about 4 miles east of Sullivan, the historic park dates back nearly as far as the Mother Road, spanning almost 7,000 acres of forested landscapes along the Meramec River. Crystal-clear springs, glades, wet meadows, and miles of tree-lined trails are among its many scenic highlights. But perhaps most unique are the 40 caves that lie beneath the park.

Formed millions of years ago, the Meramec Caverns are an impressive network of limestone tunnels that stretch 4.6 miles and feature five levels of unique geological formations. With over 7,500 caves across the state, Missouri is nicknamed "The Cave State." Meramec Caverns is its largest commercial cave — and one of its most-visited. You can book a guided walking tour that leads through the caverns' chilly passageways, descending deep into the earth. Along the way, you'll see some of the rarest cave formations in the world, including the Wine Table, an ancient structure formed completely underwater.

During your visit, be sure to check out the Jesse James Wax Museum. Legend has it that the notorious outlaw used the caves as a hideout in the 1870s, and the museum is filled with lifelike wax figurines and artifacts connected to the man himself. When you've had your fill of underground adventures, soar above the trees on a seasonal a zipline tour that zips over the forest canopy and the Meramec River at speeds of up to 50 mph. For slower-paced outdoor thrills, consider taking a day trip to Saint Robert. Located an hour west of Sullivan, Saint Robert is a small city surrounded by serene outdoor spaces and recreation, as well as a cheekily-named pit stop — the Uranus Fudge Factory.