The Midwest has some of the most charming small towns that you will ever come across. If you have driven the many scenic byways that crisscross the Midwest, you may have seen road signs for many of these. Here is a list of some of my favorite Midwest small towns that offer a charming experience that you will not find anywhere else. Each of these towns has fewer than 30,000 people, and they each have something special that sets them apart from other small towns across the Midwest.
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Note: Some of the information in this article was obtained during a sponsored trip. All opinions are my own.
1. Medora, North Dakota
Medora is one of the cutest, most charming mountain towns that I have ever visited. With fewer than 130 residents, it’s bursting with experiences that will be sure to leave you with a lasting impression. The entrance to the South Unit of Theodore Roosevelt National Park is in the town of Medora. This national park is one that offers outstanding hiking trails as well as wildlife viewing unlike any other national park. The bison, prairie dogs, and wild horses offer hours of entertainment in one of America’s most beautiful national parks. The streets of Medora are filled with unique shopping experiences as well as historical sites. For a Western experience in a small town, Medora cannot be beaten by any other town in America.
2. Elk Horn, Iowa
Elk Horn is home to the largest rural Danish settlement in the United States and home to around 600 residents. It’s located approximately one hour east of Omaha on I-80 in Southwest Iowa. The charm of Main Street will inspire you to learn more about the Danish community and why the people of Elk Horn enjoy sharing their Danish Heritage with everyone. The beauty of the rolling hills along the drive into town will remain in your mind for quite some time. Fall is a particularly scenic time of year to make this drive, as the fall colors are in full force. As you drive into town, you will come upon the Danish Windmill. Pull into the parking lot and explore the grounds of the windmill and stop inside to visit the visitors center. Plan to dine at Larsen’s Pub and indulge in an award-winning Iowa tenderloin.
3. Abilene, Kansas
Abilene is home to America’s 34th President, Dwight D. Eisenhower, and home to nearly 7,000 people. The charm of this community is evident as you drive in on Buckeye Avenue. The Seelye Mansion will leave an impression at first sight and you will be planning your tour of this historic mansion. The downtown area is home to numerous antique shops, which makes for a perfect day of antiquing in the charm of Abilene. The Dwight D. Eisenhower Presidential Library, Museum, and Boyhood Home is handicap accessible and should be a top priority when in town. Plan to spend a good two hours in the museum, as there are many interactive things to see and do. If you visit in the summer, make time to stroll through the Eisenhower Park Rose Garden; it’s absolutely breathtaking.
4. Mason City, Iowa
Mason City was home to Meredith Willson. He is best known for his work on the Broadway musical The Music Man. You can visit his boyhood home and visit Music Man Square, which is a replica of the streetscape from the production of The Music Man. A few blocks to the west, you can cozy up for a night’s stay at the Historic Park Inn Hotel, the last operating hotel designed by Frank Lloyd Wright. This property showcases all of Wright’s work and it’s a charming night of luxury in downtown Mason City. The lower ceilings and beautiful stained glass windows are truly a reflection of his work. History, music, and art all come to life in this Midwestern community of fewer than 30,000 residents.
5. Galena, Illinois
The charm of Galena is visible as you enter the town and have a view of Main Street. The historical buildings offer stunning architecture with a killer view of the downtown area. Make time to stroll the streets of Galena. One of my favorite things to do in Galena is to grab an ice cream cone at the American Old-Fashioned Ice Cream Parlor located on North Main Street. A unique view of Galena is offered from the property that the Ulysses S. Grant Home sits on across the Mississippi River. A beautiful photo opportunity is in front of you as you stand with your back to the historical home. The steeples alone make the view an exciting one. Galena will not disappoint, and I can guarantee that you will be planning a return visit before you depart the area. Golfing, hiking, kayaking, and historical walks are all outdoor experiences in this charming Midwestern community of under 4,000.
6. Charlevoix, Michigan
Charlevoix is located along the shores of Lake Michigan, Round Lake, and Lake Charlevoix in Northern Michigan. It is home to nearly 2,500 residents and offers charm and seemingly out-of-this-world experiences, including the World’s Largest Cherry Pie. When you come into downtown on the hill, you will have an aha moment. The charm of this little community nestled between the lakes is something you will fall in love with. And if you enjoy dreaming, why not take a drive around the lake and view the beautiful homes that line the lakeshore? Wrap up your day in one of several restaurants that are sure to keep your taste buds happy.
7. Winterset, Iowa
Winterset is located a short drive from Des Moines in Central Iowa. 5,400 people call Winterset home, making it a small town that poses big. Here is where you can experience the charm of the Bridges of Madison County as you drive the Covered Bridges Scenic Byway. The roads meander through the countryside as you navigate the rolling hills in the area. Summertime is a fabulous time to visit this town as the wildflowers are stunning. The Town Square is also beautiful, as the square is lined with numerous hanging baskets of beautiful flowers. There are several bridges in the area and you can easily spend a full day exploring the bridges and Winterset. John Wayne’s Birthplace and Museum are also open to visitors near the Town Square.
8. WaKeeney, Kansas
WaKeeney is a small town in Western Kansas with fewer than 2,000 people. They have a charming community that is known as the Christmas City of the High Plains year-round. This small town is known to have the largest annual tree lighting and downtown Christmas displays between Kansas City and Denver. Shiloh Vineyard and Winery is a short drive from WaKeeney and will top off your experience in the area with a glass of wine with a view. For a memorable night’s stay in this small community, stay at the 1906 Cottage Garden. Mary is your host and she runs a comfortable cottage for travelers to book a cozy night’s stay in WaKeeney. Stroll the streets and take a moment to reflect on how easy it is to slow down and enjoy life.
9. Clear Lake, Iowa
Clear Lake is home to a lake and one of the best 4th of July festivals in the United States. Stroll this charming Main Street and grab a sandwich from Starboard Market and a cup of coffee from Cabin Coffee. Hop on your bike and ride around the lake or through the quiet neighborhoods that surround the lake. A visit to the legendary Surf Ballroom should be on your list of things to do when you visit Clear Lake. You can even hike out to the Buddy Holly Crash Site, which lies a few miles north of town. The history and charm of this small lake town community in Northcentral Iowa will welcome you as you embrace time at the lake. For a town of some 8,000 residents, it sure knows how to provide visitors with a wonderful experience.
10. Arthur, Illinois
Arthur is a community in Eastern Illinois that is home to nearly 3,000 residents. It is home to the largest and oldest Amish community in Illinois and was founded in the 1860s. This charming community will lure you in with the baked goods in the bakeries, which can be spotted all around town. There is not a bad meal to be found in Arthur. For a unique experience, book a ride with an Amish gentleman and ride through the countryside with a horse and buggy. This is the best way to see the charm that this area of Illinois has to offer. Fall also brings pumpkins and fall foliage that are not to be missed, especially while the temps are still warm.
11. Pella, Iowa
Pella is home to America’s Dutch Treasure. The minute you step foot onto the pavement in Pella, you will fall in love with the charm of this community of under 11,000. If you have never been to the Netherlands, why not experience it in Pella? The tallest working grain windmill in the United States is here as are heritage museums and delicious pastries. The historic downtown is home to unique shops, some of which sell Dutch products, as well as American boutique shops. As you stroll through town, you will come upon Klokkenspel, a clock that goes off on odd hours and rings throughout the downtown. Spring brings tulips and as summer progresses, colorful flowers can be spotted throughout the community. The annual Tulip Time Festival brings hundreds of thousands of visitors to Pella, as the Dutch heritage is celebrated on an annual basis.
Each of these small, charming towns brings something unique to the Midwest. The history, arts, and even food experiences will live in your mind for a long time. Many of these communities also offer activities during all four seasons. Summer in the Midwest brings out the flowers and warm temperatures for outdoor activities. If you bundle up in layers, the Midwest also offers many great opportunities for winter experiences. A challenge that I would give you, is to visit each of these communities during each season. The Midwest has four distinct seasons with charm that looks different in each month of the year. If there is one thing that I know for certain, it is a guarantee that each community on this list will welcome you into their town. With a little luck, you may find the next place you want to call home — or at least make a repeat vacation destination.
