10 Of The Most Eccentric Towns In Missouri
The most eccentric towns in Missouri welcome newcomers with a bevy of warm hospitality, natural beauty, and cultural legacies to admire and appreciate. From the historic river towns along the Missouri and Mississippi Rivers to quirky and charming inland communities, travelers will be embracing the treasured attitude and etiquette of each Missouri village while also being surprised and awed by the nuanced eccentricities of these superb small towns. This year, find out why these are some of the most eccentric towns to visit in Missouri, whether because of the unique and compelling histories that shaped them or the natural and cultural wonders to gawk at from these humble abodes.
Boonville
Boonville sits gracefully along the Missouri River, where a charming small-town ambiance meets architectural richness. Its Historic District features exquisite Late Victorian and Classical Revival storefronts and churches, evoking the grandeur of a 19th-century Midwestern town. You might also feel gravitated towards the Hotel Frederick, a lovingly restored 1905 boutique hotel that captures the elegance of a bygone era. Aside from these small moments in history, Boonville also features an eccentric landmark known as the Mitchell Antique Motorcar Museum, which showcases rare automobiles from the early 20th century.
Meanwhile, the town’s lively calendar features eccentric events like the Big Muddy Folk Festival in April, celebrating regional music traditions, and the Missouri River Steam Engine Festival in September, where vintage machinery roars back to life. For a touch of nightlife, the Isle of Capri Casino Hotel offers gaming, dining, and live entertainment, adding a modern twist to Boonville’s historic setting. Whether you are strolling through antique shops, attending a festival, or watching the river flow by, Boonville provides a warm, welcoming glimpse into Missouri’s history while accommodating many with a taste for adventure.
Hermann
The eccentric town of Hermann, just halfway between Jefferson City and Saint Louis along the Missouri River, enchants visitors with its thriving German heritage for all to cherish and savor. Located in a region in the state known as the Missouri Rhineland, Hermann hosts the beloved Hermann Wurstfest each March, a flavorful festival featuring sausage tastings, kraut-making classes, German music and dancing, as well as a famous Wiener Dog Derby to bolster its unique and eccentric blend of cultures from the US and Germany. Similarly, the Hermann Antique Show in April sees dozens of antique dealers selling their wares at the Historic Festhalle at the Inn at Hermannhof, making Hermann an excellent spot to purchase all sorts of antiquated goods.
Famed establishments like Stone Hill Winery, Hermannhof Winery, and the historic Adam Puchta Winery, the oldest continuously family-owned winery in the nation, all offer scenic vineyard tours and excellent wine tasting sessions that everyone can try. Last but not least, the Katy Trail runs through the area and encourages everyone to bike or stroll through the picturesque countryside.
Kimmswick
Just south of Saint Louis, the historic town of Kimmswick is a quaint riverside village in America’s Heartland, a place brimming with a number of historic eccentricities and oddities. Among these fantastic landmarks and relics to see are those found in the Mastodon State Historic Site, open year-round and featuring a museum with a life-size mastodon skeleton replica, interactive exhibits, picnic areas, and accessible trails. Nearby, the Anheuser Estate & Museum preserves the farming legacy of Fred and Mabel Ruth Anheuser, founders of the world-famous Budweiser Beer, whose homestead offers peaceful and informative tours tied to Anheuser-Busch heritage.
Every June, the Strawberry Festival fills the town with sun-ripened berries and community cheer, while in October, the Apple Butter Festival enlivens the air with cozy, simmering sweetness. Both events draw crowds for their homey, family-friendly fun. With a plethora of eclectic and eccentric attractions and activities to seek out, Kimmswick is a welcoming and surprising destination worth experiencing on the Mississippi River.
Arrow Rock
Just a short drive from Boonville along the Missouri River, Arrow Rock sits within a designated National Historic Landmark District, echoing with tales of Native American flint-knapping and frontier exploration. Centuries ago, its bluffs—marked on a 1732 French map as pierre à flèche (rock of arrows)—offered flint that Native Americans used to shape their arrowheads. Today, the Arrow Rock State Historic Site Visitor Center brings this indigenous and pioneering history to life through engaging exhibits and interactive programming.
After stepping inside the past, travelers can slow down and savor a meal at the venerable J. Huston Tavern, a rustic and charming spot that has welcomed travelers since the early 19th century. Many more of you might also be interested in touring the Arrow Rock Historic District, with its well-preserved pioneer architecture, mementos, and other artifacts to note. Best of all, you can go traipsing and wandering through the Jameson Island Unit that the Missouri River regularly feeds with life-nourishing waters and other habitats.
Hannibal
Infused with literary lore, Hannibal is famously the boyhood home of Mark Twain, whose tales continue to enchant and invite newcomers from all over. When beginning your journey through this literature-inspired village, you ought to first pay a visit to the Mark Twain Boyhood Home & Museum, where the great writer’s childhood residence, writing desk, and personal artifacts illuminate Samuel Langhorne Clemens’ (his real name) formative years.
A scenic cruise aboard the Mark Twain Riverboat lets you glide down the Mississippi River and imagine Twain’s riverine adventures. Similarly, the Mark Twain Memorial Lighthouse offers photo-perfect sceneries of a landscape that Twain might have played around in in his youth. Last but not least, the Mark Twain Cave, one of the inspirations behind Tom Sawyer, entices travelers with winding passages and stories of Wild West outlaws and freedom fighters. With its insightful histories and its literary references, Hannibal is a handsome little destination for travelers all over.
Carthage
Carthage, located on the Spring River, about an hour west of Springfield, is lauded as the “Maple Leaf City” and continues to capture the spirit of revival and resilience after its many tribulations in the American Civil War. The Battle of Carthage Civil War Museum chronicles the town’s endurance and steadfastness in this pivotal period, where artifacts and narratives bring regional history into sharp and comprehensive focus. Carthage earned a reputation for wealth during the late 19th century thanks to lead and zinc mining, and remains proud of that heritage with several galleries and shops that continue to sell zinc and lead items.
Each October, the spirited Maple Leaf Festival transforms downtown with maple syrup samples, craft booths, live music, and autumnal splendor. Also drawing visitors is the awe-inspiring Congregation of the Mother of the Redeemer statue, serving as a landmark for the vibrant Marian Days pilgrimage celebrated by Vietnamese-American Catholics every August. Being a popular pilgrimage site for various reasons, Carthage is as grand and noble a settlement as its ancient namesake from so long ago.
Branson
Branson buzzes with energy and entertainment, making it an eccentric and enthusiastic escape for families and music lovers alike. Along the vibrant 76 Country Boulevard, theaters dazzle with country shows and live performances throughout the year. One can discover curiosities at the Titanic Museum Attraction, where preserved artifacts showcase the morbid tragedy that befell the Titanic. Other oddities include Ripley’s Believe It or Not! Museum, featuring everything from shrunken heads to quirky artworks.
Car aficionados will love the Branson Auto & Farm Museum, where vintage tractors, cars, and memorabilia line the halls. For thrill-seekers, Silver Dollar City offers rides and themed attractions. At the same time, nearby Table Rock Lake invites outdoor adventure to places like the Dogwood Canyon Nature Park and the Lost Canyon Cave & Nature Trail. Having a wide array of eccentric and entertaining attractions, Branson is a brand-new experience for newcomers and even regular visitors from all over.
Osage Beach
Set amidst the lush Ozark Mountains, the small town of Osage Beach is a gateway to outdoor fun and relaxed lakeside living. One can spend their eccentric days kayaking, swimming, or casting a line on the inviting Lake of the Ozarks, a watery basin of opportunities and mysteries within the dynamic heights of the Ozarks. Beyond the water, the sprawling Lake of the Ozarks State Park offers miles of hiking trails, scenic overlooks, and family-friendly camping spots to lounge and relax in the mountains of Missouri.
Those with curious appetites can appreciate the various informative exhibits at the Ozark Caverns Visitor Center, where you can explore hidden chambers and limestone formations in subterranean systems near town. Meanwhile, the peaceful Saline Valley State Wildlife Area beside the Osage River invites quiet wildlife watching and gentle hikes. Just around 45 miles from Jefferson City, newcomers to Osage Beach will have a glorious and glamorous time in this eccentric little town in the Ozarks.
Marceline
Marceline, Walt Disney’s boyhood hometown, is a creative and Disney-inspiring destination with many eccentric amenities to cherish. The Walt Disney Hometown Museum, housed in the old Santa Fe Depot, showcases Walt Disney’s family memorabilia, rare sketches, and artifacts that inspired the creative genius of the man. When strolling through Kansas Avenue, Marceline’s Main Street, it will feel like passing through the very streets that inspired Disneyland’s own Main Street USA. Meanwhile, the Walt Disney Dreaming Tree and Barn stands as an intimate homage to childhood imagination rooted in Missouri fields.
If Disneyland caters to the modern attractions that kids from all over know and love, then Marceline caters to those more interested in the man who inspired the childhood wonders all know and adore.
Sainte Geneviève
As Missouri’s oldest European-settled town, built by French Canadian settlers in 1735, Sainte Geneviève has remained a living tapestry of French colonial heritage. At the Ste. Geneviève National Historical Park, you can marvel at impeccably preserved homes and gardens from the 18th century that illuminate the colonial lifestyle that early settlers had to endure. Nearby across the Mississippi River, sites like Fort Kaskaskia and the Pierre Menard Home in Illinois offer further insights into the region’s colonial leadership, settlement, and frontier history.
Cultural celebrations in town include the French Heritage Festival each June, with folk dancing and traditional music, as well as the Jour de Fête, a massive outdoor crafts fair held in mid-August that brims with artisans showcasing handmade goods. With its many French-themed activities and amenities, Sainte Geneviève is a baroque and beautiful small town that harkens to the laidback simplicities of one of France’s own little villages in the countryside.
Missouri’s Most Delightfully Quirky Towns
Whether you are following the flow of Missouri’s many rivers, strolling in the footsteps of a renowned author or movie genius, or breathing in traces of early settlers’ lifestyle, the most eccentric towns in Missouri each provide a plethora of authentic experiences and welcoming landmarks to seek out. A literary legend comes alive in the small town of Hannibal, just as an era-defining animator can be appreciated in Marceline. French-colonial livelihoods and etiquette can be seen in places like Sainte Geneviève, while destinations like Osage Beach guide people towards the breathtaking splendors of the outdoors. Ultimately, these eccentric and exciting small towns to visit in Missouri will not be forgotten nor dismissed for very long. In 2025, you ought to go see for yourself why everyone is talking about these eccentric small towns to visit in Missouri.
