While Missouri is a largely rural state, over half of the population was living within the Kansas City and St. Louis metro areas as of 2021. It is easy to see how the littlest towns get overlooked, with their historic downtowns, waterfronts, and surrounding nature often untouched by the urban footprint. Most eager to get a cultural rush, they open their hearts to tourists, like Boonville and Parkville along the illustrious Missouri River. Camdenton, home to the Ozarks Amphitheater, welcomes you to a lakeside lifestyle.

The small town of Cuba features one of the few remaining drive-in theaters in the state for an atmospheric evening. Its moniker, Route 66 Mural City, conveys the galore of experiences for daytime. Every single one of these six charming overlooked towns deserves a second look, starting with Boonville, a Civil War site with modern-day attractions like Lions Park Aquatic Center and the Isle of Capri Casino and Hotel.

Boonville

Overlooked despite convenient access on Interstate 70, this beautiful town on the Missouri River is a must-see for a culturally enriching experience. Halfway between Kansas City and St. Louis, Boonville, the site of one of the first land battles of the American Civil War, paints the landscape with landmarks, a fun way to explore the area, like the Katy Trail. Visitors can prowl through sights and small-town businesses along the 400 buildings on the National Register of Historic Places for local treasures, including shopping, dining, and theater venues. Welcoming you with over 450 hotels and bed and breakfast rooms, as well as regular events and festivals, there are loads of entertainment for every age and taste.

Explore at your leisure or join a walking tour for interesting remnants of earlier times in this old railroad town, now with lively cultural and artistic scenes. In between the notable stops for the whole family, like car museums and historical societies, there’s a whole lot of natural beauty through the Katy Trail State Park and to soak up at the riverside. Families enjoy the expansive Boonville Lions Park Aquatic Center, while the Isle of Capri Casino and Hotel is a great way to experience local hospitality and gamble for another night’s stay. Make it a day’s itinerary to the nearby historic small towns like Rocheport, Blackwater, and Arrow Rock.

Camdenton

It is a shame that the unique town of Camdenton is often overlooked, hidden along the shores of the beautiful Lake of the Ozarks, with a plethora of natural charms in the outdoor area to explore. Whether you’re in for the popular summertime or the shoulder seasons, the year-round small lake town delights families with attractions like the Adrenaline Zipline in the fall colors. Minutes southwest, one of the nation’s best state parks, Ha Ha Tonka State Park, has something for every outdoor enthusiast, including rafting adventures and the Niangua River Oasis. The festivals, like Festival Faye May and the outdoor Ozarks Amphitheater, are an exclusive experience here.

This tiny town of just 4,000 residents meets the summertime demand with charming B&Bs and resorts on the Lake of the Ozarks, with easy access to all those great activities. Home to friendly townspeople, visitors can mingle among them along an array of parks and trails, as well as venues for each taste of entertainment, like Ballparks National or Jon’s Rock & Roll Theater. From the numerous restaurants and bars like El Caporal Mexican Restaurant to the several local shops with little treasures you won’t find anywhere else, don’t miss the Old Kinderhook Ice Rink-Sand Volleyball at the appropriate time of year.

Cuba

The small town of Cuba, a two-hour drive from St. Louis, is overlooked yet has all-tourist allure for the bright future. A must-visit any time of the year, Cuba hosts the popular Crawford County Fair in July, and every corner is Instagram-worthy in this historic town, aka Route 66 Mural City. The fair is an over 70-year-old tradition with family activities and events at Hood Park, like agricultural exhibits, pageants, live concerts, food, and carnival rides. The welcoming vibes make it easy to feel part of the picture over only local experiences, like one of the few remaining drive-in theaters in the state on a warm-weather evening.

This pretty little town of about 3,000, where art meets history, is also about driving and wining, which makes it a hit place for every taste for a fun getaway. Nestled right up against Route 66, which runs through the heart, adventures await. At the intersection with Highway 19, Weir on 66 offers a unique dining experience—a new take on an old tradition—of a 1931 Phillips 66 Station. Likewise, don’t miss the Historic Landmark Wagon Wheel Motel and Connie’s Shoppe, the Route’s oldest operating motel. From the many historically important attractions around the Mother Road to the street murals and little hotspots for local food and memorabilia, snap a memento by the big red rocking chair!

Hollister

This small and eclectic town, comprising a few neighborhoods with Downing Street on the National List of Historic Places, is replete with cute businesses. From a saloon to a rafting outfitter and guide and a day spa, grab a bite at the gumbo seafood shop or the Mexican restaurant. Don’t miss the brand-new art loft and gallery, all of which inspire feel-good browsing for tourists. Truly a remarkable town, a sister city of Branson, Hollister graces the southern shores of Lake Taneycomo, often overlooked for the pizzazz of the latter town. Offering softer appeals like a stroll along the Downing Street Historic District, the stonemasonry is remarkable, including beautiful Tudor-style buildings that look straight from an English village.

Along this historic, tree-lined thoroughfare, the iconic Ye Olde English Inn, also on the Register, offers a great rest to discover this town, with pub-grub comfort food on-site and a dozen golf courses. Over a few days of active exploration and relaxing evenings, the fresh Ozark air will clear your lungs of the city soot. The outdoorsy can enjoy a kayak paddle or a canoe for rent in town along the serene White River, while the nearby Table Rock Lake, home to the famous public beach, is a hit in the summertime, with swimming, boating, and lovely shoreline walking paths. In addition, the riverfront Table Rock State Park on Hollister’s side offers a great campground to get away on a budget with a network of excellent hiking trails.

Parkville

Snug up against Kansas across the Missouri River, Parkville, a small city in southern Platte County, is a quintessential riverside escape. Minutes from Kansas City Downtown, the historic town offers a smattering of village greens between antique shops, art galleries, and old architecture for lovely strolls. Boasting its own Park University, Parkville stays youthful throughout the school year with cafes and a spirit of innovative rigor, which makes it one of the Midwest’s most exciting, before turning serene along the riverbanks. Don’t miss the mega-popular Nick & Jake’s after an afternoon at the nearby riverfront English Landing Park.

From Parkville’s historical beginnings to a modern-day culture of creativity, visitors will have a hoot discovering this little town against the most illustrious backdrop. Composed of limestone-carved bluffs, wooded vistas, and the refreshing Missouri River, it is a call to every type of adventurer. In the summer months, tourists can relax on a stroll, picnic, and enjoy sunset views, as well as take advantage of the local National Golf Club, which has two great golf courses.

Sikeston

Despite being the largest town in Scott County, Sikeston, often considered the start of the bootheel and the cotton in Missouri, is shamefully overlooked along Interstate 55, right in between St. Louis and Memphis, Tennessee. Established in 1853 along the prairies, visitors can explore the proposed railroad route where it crossed the old El Camino Real. The Kings Highway, from the days of Spanish control, is now the Kingshighway, aka the Business US, the primary north-south thoroughfare in Sikeston with a smattering of businesses and old architecture like a railroad depot. From 10 motels to over 40 restaurants, impressive for a small town of about 16,000, prowl through shopping districts, art, antiques, and specialty shops in Historic Downtown Sikeston, with a stop at Lambert’s Cafe to see why it is world-famous.

Much like its history, Sikeston was built upon a wild and varied landscape of cypress swamps, marshes, and bayous to the bottomland forests of oak, hickory, gum, cottonwood, and wild sycamore. Only a small village-supply depot during the Civil War, the crossroads location attracted action. Confederate General Jeff Thompson allegedly hid money from the bank he robbed in Charleston under one of the oak trees at the corner of New Madrid Street and Kingshighway, while Federal General John Pope used the town as a garrison in 1862, awaiting heavy guns from Cairo, for the planned Siege of New Madrid. Today, this fun, new town to discover connects tourists with the history at the historic Sikeston Train Depot and Museum and local nature in the summer. Offering two campgrounds, families can get away on budget for an authentic taste of southern Missouri culture at the local rodeo in August!

These six unassuming towns offer the authentic Midwest experience for every taste of travelers, like limestone-carved bluffs, wooded vistas, and the refreshing waters in the riverside town of Parkville along the great Missouri River.

When in Hollister, don’t miss a stay at the iconic Ye Olde English Inn, on the National Register of Historic Places, and while scavenging around the historic town of Sikeston, its world-famous Lambert’s Cafe is a must-visit!