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9 Small Towns in Missouri Worth Stopping For

Growing up in Maine, we had no shortage of small towns to visit. I loved driving through the main streets of these towns, stopping for a slice of pie, and wandering through historic sites. When I moved to Missouri 20 years ago, I had a whole new list of small towns to explore. My in-laws gave me a “Day Trips from Kansas City” book, and I was off! The state of Missouri is twice the size of Maine with five times more people but there are still plenty of small towns right outside of bigger cities and in the middle of cow pastures. These small towns in Missouri are not to be missed. All have populations of less than 25,000 people.

1. Hermann

Hermann – Population: 2,342

Hermann in town to seven wineries in Missouri.
Missouri Division of Tourism

Hermann was founded by the German Settlement Society of Philadelphia in 1837. The city is home to seven wineries that produce roughly one-third of the state’s wine.

In 1983, it was designated as one of the first-federally recognized American Viticultural Areas. This designation recognized the renaissance of an area of vineyards and wineries established by German immigrants during the mid-19th century.

Hermann is known for its cultural festivals including a Maifest–a German festival to celebrate the arrival of Spring–the third weekend in May and an Oktoberfest the first four weekends in October. Hermann also refers to itself as the sausage-making capital of Missouri. You’ll find several restaurants and sausage makers in town.

2. Jamesport

Jamesport – Population: 513

Jamestown, Missouri, home to the largest Amish community in the state
Missouri Division of Tourism

For a town with a population around 500 people, it punches well above its weight as a place to visit. With the largest Amish community in the state, you’ll find many small businesses selling hand-made furniture, food items from baked goods to canned items, and plenty of antiques.

It’s easy to spend a day there walking through town and dining at places like the Gingerich Dutch Pantry Restaurant. And, if you want to stay the night, they also have a couple of Bed and Breakfasts and Inns to choose from.

3. Excelsior Springs

Excelsior Springs – Population: 11,731

Hall of Waters & Excelsior Springs Visitor's Center

Located just 30 miles outside of Kansas City, Excelsior Springs is a very popular small town for a weekend getaway. Whether you’re looking for a romantic spa experience at one of the oldest hotels–operating since 1888–or a historic walk through the Hall of Waters, this is a fantastic place to visit.

They have something for everyone from a brewery to the Slightly Off Broadway Theater. You’ll also find plenty of restaurants and even a golf course.

4. Weston

Weston – Population: 1,815

Old-Fashioned gas station in Weston, Missouri

Located a little north of Kansas City, you’ll find the town of Weston. Known for several destination festivals, it’s a great locale for a weekend trip.

The main street area is full of local shops and restaurants and is very walkable. As with many small towns, you’ll find antiques but you’ll also find wineries, premium hand-rolled cigars made on-site in a tobacco drying barn, and a brewery.

Whether you’re looking for those things or a great hike, a place to pick apples, or a whiskey snug, Weston does not disappoint. There’s a little bit of everything for everyone.

5. Rocheport

Rocheport – Population: 254

Life slows down a little in Rocheport, in the best way. As you drive across the state of Missouri, you’ll come across Rocheport halfway between St. Louis and Kansas City.

Les Bourgeois Winery in Rocheport, Missouri
Missouri Division of Tourism

You’ll definitely want to book a stay at the School House Bed and Breakfast which is housed in a school built in 1914 that used to be a four-room school for 1st-12th graders. It’s now listed on the National Register of Historic Places.

You’ll have plenty to explore between Rocheport’s Les Bourgeois Winery, a general store with live music, and delicious dining options. For the more adventurous, you can even bike through on the Katy Trail for a visit.

6. Boonville

Boonville – Population: 8,439

Katy Trail State Park in Boonville, Missouri
Missouri Division of Tourism

Named after Daniel Boone, Boonville was shaped by its proximity to the Missouri River, the development of the railway, and the Civil War. Today, the town boasts many historic sites including the River, Rails and Trails Museum, the Mitchell Antique Motorcar Museum, and a walking tour with more than 400 sites and structures to see.

If you’re looking for more than history, the town also has plenty of places to eat, shop, and explore. You can even take a sneak peek tour of the town by clicking here.  

7. Kirksville

Kirksville – Population: 17,602

Kirkville town square
Photo courtesy Jenn Beard

Kirkville is a fun and quirky college town. Home to Truman State University and A.T. Still University, home of the Kirksville College of Osteopathic Medicine and a fascinating museum about the origins of osteopathic medicine.

At Thousand Hills State Park, where you can rent a pontoon boat for the day, take a swim, or go fishing. If you’d rather relax with a glass of wine and some live music, check out West Winery at Jackson Stables.  

8. Sedalia

Sedalia – Population: 21,629

Katy Depot in Sedalia, Missouri
Missouri Division of Tourism

Sedalia is a great day-trip from Kansas City. With the State Fair, the Scott Joplin Ragtime Festival, and another portion of the Katy Trail running through it, it’s easy to see why.

Visitors should start with the Katy Depot which houses the town’s welcome center, a railroad exhibit, and is a trailhead for the Katy Trail State Park. From there you can explore everything from art at the Daum Museum of Contemporary Art to the Trail of Tails, following cats around town to learn about the town.

With the popularity of the fairs that come to town, you’ll find plenty of great places to stay and dine as well.

9. Rolla

Rolla – Population: 20,431

At the midway point between St. Louis and Springfield, you’ll find Rolla. The town is best known as the home of the world-renowned Missouri University of Science and Technology. However, even if you’re not there to visit or attend the university, there are plenty of other reasons to come to town.

It’s the headquarters for the Mark Twain National Forest, which includes 1.5 million acres of public land that span across natural wonders in 29 counties in Missouri. Named for Missouri native, Mark Twain, you’ll find wildlife, streams, caves, forests, and more nestled along more than 750 miles of trails.

Beautiful and memorable small towns in Missouri you should visit, including Hermann, Boonville and Weston.

About the Author

Jenn Beard is the founder of Cocktails Away—a collection of adventures in pursuit of a great drink, a quality spirit, a unique ingredient, and the places they come from. When not traveling, she lives in Kansas City. Check out her blog for mouthwatering recipes and insider tips on DIY bartending and cocktail culture or travel to bars around the world at @cocktailsaway.

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Deborah Larsen

Saturday 23rd of October 2021

Many on the list are not small town America. Plus they left out all of southeast Missouri! How about Kimmswick, Ste Genevieve and Cape Girardeau?


Saturday 23rd of October 2021

Southeast Missouri is a region I've yet to explore. I'll add those towns to my to-visit list!

Matt Rector

Wednesday 20th of October 2021

You left off Eminence. Some of these are not even small. Lol

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