The Fourway diner in Cuba, Missouri, located on historic Route 66. Image credit StockPhotoAstur via Shutterstock

7 Of The Quirkiest Towns In Missouri

Known as the "Show Me State," Missouri proudly shows its charm through quirky towns that dot its landscape. From Kimmswick in eastern Missouri to Carthage in the southwest and several places in between, Missouri's small towns offer an eccentric blend of roadside attractions, annual festivals, and eclectic art communities. Several of these towns provide one-of-a-kind exhibits with unique views of everyday items, such as sliced bread, bridal gowns, and porcelain figurines. For travelers who enjoy art and historical architecture from the 1700s and love exploring vintage sites along Historic Route 66, discover seven of the quirkiest towns in Missouri to explore.

Chillicothe

Beautiful Downtown Chillicothe, Missouri.
Beautiful Downtown Chillicothe, Missouri. Image credit: J. Stephen Conn via Flickr.com

Located in Northern Missouri is Chillicothe, one of the most whimsical towns in the "Show Me State." Known as "The Home of Sliced Bread," the town gets a rise out of its bread heritage. In 1928, the Chillicothe Baking Company was the first company in the nation to sell sliced bread. Today, visitors can learn more about the town's bread history at the Chillicothe Welcome Center and view a large bread mural in the historic downtown. 

For even more history of Chillicothe, the Grand River Historical Society Museum provides a unique glimpse into the town's past. The exhibits showcase the everyday lives of individuals and families from the community, including a soda fountain from Main Street, a working train whistle, and military uniforms worn by local veterans. Located near the museum is Simpson Park, the site of memorable outdoor activities and annual events, such as the Freedom Festival in July and the Annual Chillicothe Car Show, featuring classic vehicles. The park is also home to one-of-a-kind wood carvings made from trees dying in the park. Outdoor enthusiasts can also walk the one-mile path in the park under 200-year-old trees.

Hannibal

Downtown street in Hannibal, Missouri.
Downtown Hannibal, Missouri. Editorial credit: Sabrina Janelle Gordon / Shutterstock.com

Hannibal, the childhood hometown of author Mark Twain, offers a treasure trove of unique activities and attractions. Outdoor enthusiasts enjoy exploring Mark Twain Cave, Missouri's oldest show cave, discovered around 1820. As a child, Mark Twain played in the cave's labyrinth, which inspired his renowned work, The Adventures of Tom Sawyer. Located in town along cobblestone streets is the Mark Twain Boyhood Home & Museum. After exploring the author's home, nature lovers can stroll along the riverwalk on the banks of the Mississippi River, featuring a statue of Mark Twain as a steamboat pilot.

History buffs can explore stories of other notable figures from the town at the Hannibal History Museum. Uncover tales of Cliff Edwards, the voice behind Walt Disney's Jiminy Cricket, baseball legend Jake Beckley, and the "Unsinkable" Molly Brown, who survived the Titanic's tragic sinking in 1912. Explore the captivating story of Molly Brown at the Molly Brown Birthplace and Museum, located in the 1867 cottage where she was born.

Cuba

A vintage car next to a rock building on Route 66 in Cuba, Missouri.
A vintage car next to a rock building on Route 66, Cuba, Missouri. Image credit Logan Bush via Shutterstock

Located along Historic Route 66 is the unique town of Cuba, Missouri, where art and history meet. Home to an eclectic arts community, the town's historic Main Street features 14 murals. The Murals of Cuba share the unique history of the town, including President Harry S. Truman's 1940 political campaign in the town and when Amelia Earheart was forced to stop near Cuba on September 4, 1928, during her flight to Los Angeles

More history can be uncovered at the Crawford County History Museum. The museum displays several distinct exhibits, such as the Hall of Bridal Gowns, featuring gowns from the 1890s through the 1970s. For outdoor enthusiasts, Cuba is located just north of the Meramec River, which offers waters for fishing, canoeing, and floating. After a day of outdoor adventures and exploring the quirky town, visitors can stay at the Wagon Wheel Motel, the oldest continuously running motel on Historic Route 66. Listed on the National Register of Historic Places, the motel is known for its original 1947 flashing neon sign.

Carthage

Restored vintage Phillips 66 Gas Station located at Red Oak II, Carthage, Missouri
Restored vintage Phillips 66 Gas Station located at Red Oak II, Carthage, Missouri. Editorial credit: Nick Fox / Shutterstock.com

Carthage, situated in southwest Missouri, blends quirky charm and unique sites with nostalgic art in the Ozark Mountains. One of the most unique sites in town is the Precious Moments Chapel, created by artist Sam Butcher. With more than 9,000 square feet, the chapel showcases 84 murals, 30 stained-glass windows, and a gift shop of the porcelain Precious Moments figurines. Visitors can also get their kicks in Carthage along Historic Route 66. The road boasts the 66 Drive-In movie theater and the Boots Motel, where actor Clark Gable stayed in 1947. History buffs and Civil War enthusiasts can explore the Battle of Carthage State Historic Site. Fought on July 5, 1861, 6,000 Confederate troops forced Union soldiers to retreat during the pivotal Civil War battle. 

More history can be explored in historic downtown Carthage, including one of the most photographed buildings in the state, the Jasper County Courthouse. Built in 1894-95, the courthouse was built from Carthage marble in the town's square. There are also four areas in town listed on the National Register of Historic Places. With more than 600 buildings on the list, visitors can take the Historic Driving Tour to view the historic architecture.

Genevieve

The County Clerk building in Ste. Genevieve, Missouri,
The County Clerk building in Ste. Genevieve, Missouri.

Nestled along the banks of the Mississippi River is Ste. Genevieve, about a one-hour drive south of St. Louis. Settled by French Canadians around 1735, the charming town is Missouri's oldest permanent European settlement. The town celebrates its French heritage at events throughout the year, including at the Alleé Allumeé in December and events at the Centre for French Colonial Life Museum Campus. The museum offers tours of four historic homes from the 1700s and 1800s, such as the Bolduc House Museum and a living history camp each spring. Nearby is the Ste. Genevieve National Historical Park, includes the oldest home in the town, the Green Tree Tavern, built in 1790. 

The town also boasts unique views of the region's prehistoric past at the Sainte Genevieve Museum Learning Center. Although the museum showcases more recent memorabilia, such as items from the WWII Weingarten POW Camp and a bank safe that the infamous Jesse James Gang robbed, visitors are first greeted by eight life-sized dinosaurs when entering the museum. Prehistoric adventures occur in the museum's Hall of Giants exhibit and the Focus Gallery, where the egg incubator prop from the movie Jurassic Park III is displayed.

Kimmswick

kimmswick missouri
Downtown Kimmswick, Missouri. Image credit: Paul Sableman via Wikimedia Commons.

Kimmswick is a quirky Missouri town known for its historic sites and unique annual festivals. Founded in 1859, Kimmswick boasts dozens of historical buildings throughout the small town of 128 people. Visitors can explore the oldest log structure in town, the Burgess-How House and Museum, a farmhouse built in the 1850s. Nearby, on the banks of the Mississippi River, is the picturesque Anheuser Estate and Museum. Constructed in 1867, the estate is the ancestral home of Fred and Mabel Ruth Anheuser of the Anheuser-Busch Brewing Company. Travelers can tour the home to view family heirlooms and items from the 1904 World's Fair in St. Louis. Afterward, take a walk across the nearby Windsor Harbor Road Bridge. Built in 1874, it is considered the oldest wrought iron bridge in Missouri.

While strolling through the charming town, visitors must stop at the famous Blue Owl Restaurant and Bakery for their Levee High Caramel Apple Pecan Pie. Featured on several TV shows, the pie was created in honor of the levee that saved the town during the Great Flood of 1993. More tasty treats can be enjoyed during the town's annual Strawberry Festival in June and the Apple Butter Festival in October.

Hermann

Aerial view of Hermann, Missouri.
Aerial view of Hermann, Missouri.

Situated along the Missouri River is the enchanting town of Hermann. Known for blending its German roots with its rich agricultural heritage, Hermann offers unique festivals, history, and wineries to enjoy. In March, meat processors from Missouri attend Wurstfest to compete in a sausage-making contest and a Weiner Dog Derby. More German heritage is celebrated during the annual Maifest in the spring and Oktoberfest each weekend in October. Visitors can also enjoy the town's agricultural roots on the Hermann Wine Trail. Guests can sample wine at six local wineries, including Adam Puchta Winery, America's oldest, continuously owned family farm winery. 

For more history, take the Hermann Riverfront Walking Tour to view 17 historical buildings, such as the Historical Hermann Museum at the German School, which was built in 1871. Another stop on the tour is at the Hermann statue of the town's namesake. Also known as Arminius, Hermann was a hero of the Battle of the Teutoburg Forest, liberating parts of Germany from Roman rule.

These small towns throughout the "Show Me State" provide a unique glimpse into Missouri's history, vibrant art communities, and eclectic annual events. From exploring a living history camp of French settlers in Ste. Genevieve to touring the Mark Twain Cave in Hannibal, these small towns in Missouri offer offbeat attractions and exciting adventures. Whether spending time among 200-year-old trees in Chillicothe or staying at a historic Route 66 motel in Cuba, these quirky small towns in Missouri provide a memorable getaway.

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