Where are the Midwest’s Finest Little Towns?

The Great Lakes, beautiful sand dunes, and deep woods are just some of the landscape features found in the Midwest. Increasing numbers of tourists are looking inside, to the vibrant cities and bucolic landscapes of the United States’ heartland.

Small towns in the Midwest are just as worth visiting as the region’s larger cities like Detroit, Chicago, and Minneapolis. In light of this, we have selected ten of the finest communities in the region with a population of fewer than 11,000. Vacationing in the Midwest? Here’s everything you need to know.

This picturesque harbor community is close to “Located in the uppermost part of the Lower Peninsula of Michigan, the “Tip of the Mitt” is a popular nickname for the region. Visit Stafford’s Perry Hotel, where Hemingway sometimes stayed, the elegant Pour Kitchen & Bar, and American Spoon, a restaurant specializing in artisanal preserves, all located in the city’s historic center. Outdoor activities are also significant in the region, since it’s home to the world-class Bay Harbor Golf Club as well dordle as wonderful hiking along the North Country Trail and in the Bear River Valley Recreation Area. Don’t leave town without visiting Petoskey State Park and searching for the fabled Petoskey stones. Walloon Lake Winery (named after the famous lake where Hemingway’s summer villa was situated) and Pond Hill Farm (found on the nearby Tunnel of Trees route) are just two of the wineries that wine lovers should visit while in the area.

Hill City, South Dakota may only have a population of about 900 people, but they carry quite a punch. Must-sees include the Prairie Berry Winery and Miner Brewing Co. for locally made and sourced drinks, the 1880 Train for a narrated two-hour round-trip excursion between Hill City and Keystone, and the family-friendly Palmer Gulch Campground, which hosts a number of rodeos throughout the summer. Hill City is also within driving distance of key South Dakota destinations including Custer State Park, Mount Rushmore National Memorial, and Crazy Horse Memorial. Wind Cave National Park (approximately 30 miles distant) and Badlands National Park are two of the greatest in the state, and the town offers a great base for exploring both (about 90 miles away).

The municipality of Kohler, Wisconsin, in the middle of the country, was one of the earliest planned communities in the United States; its parks were built by the same landscape architect who created Central Park. The American Club, Kohler’s exquisite hotel and the only AAA Five-Diamond property in Wisconsin, is the town’s crown gem. You may unwind at the Waters Spa or play a round of golf at either Whistling Straits or Blackwolf Run. Travelers from outside the area will appreciate Kohler’s location, since it is just around 55 miles from Milwaukee and 145 miles from Chicago.

Because of its historical ties to the Netherlands, Pella is sometimes referred to as “America’s Dutch Treasure,” and it is home to both a world-famous tulip festival and a windmill that is operational throughout the year. Vander Ploeg Bakery, Ulrich’s Meat Market, Dutch Fix, and Jaarsma Bakery are a few more places with a Dutch theme. Small-batch Gouda cheese, including Gouda cheese curds, may be found at Frisian Farms Cheese House in neighboring Leighton, about 11 miles away. Lake Red Rock, the state’s biggest at over 15,000 acres, is conveniently located outside of town, making it ideal for outdoor enjoyment. Pella is an excellent alternative for a day vacation or weekend getaway because of its convenient location around 177 miles from Omaha and 45 miles from Des Moines.

The little town of Medora is the entry point to Theodore Roosevelt National Park, where the Great Plains and the beautiful Badlands meet. Drive the 48 miles around the South Unit, which starts and finishes in town, to see more of the area. In addition to seeing wildlife like bison and prairie dogs, visitors to the park may also go hiking, horseback riding, camping, and snowshoeing. Medora also has an adorable children’s park, a thrilling zip line, the innovative Pitchfork Steak Fondue, and a hip wine bar called Medora Uncork’d.

Fish Creek is one of the many attractive tiny towns in Door County, Wisconsin (often known as “the Cape Cod of the Midwest”). The highlights of the trip include a wine tasting at Lautenbach’s Orchard Country vineyard and market, supper and drinks at the Whistling Swan, and retail therapy at Sister Golden. The White Gull Inn is a must-visit for anybody interested in sampling Door County specialties like a classic fish boil or the world-famous cherry-stuffed French toast. The adjacent Peninsula State Park is a haven for outdoor enthusiasts, with its trails, lighthouse, and plenty of swimming and kayaking opportunities. Thorp House Inn & Cottages is a charming place to spend the night.

Ashland, Nebraska is located exactly halfway between the state capital of Lincoln and the state’s largest city, Omaha. Salt Creek Mercantile, Postscript, Glacial Till Cider House & Tasting Room, and many more local art galleries may be found in its lovely and accessible downtown shopping center. The neighboring Strategic Air Command & Aerospace Museum is also worth a visit for aviation and history aficionados, since it has a flight simulator. A lovely golf course, Iron Horse Golf Club, can be found just outside of town, and nearby Eugene T. Mahoney State Park is a great place to take the kids or go hiking.

Southeast Minnesota is home to this picturesque tiny hamlet, which is perched on the hills above the flowing Root River, a favorite tubing destination. The Root River State Trail is a great route for cyclists in the state. Stop into Parkway Market & Coffeehouse, Another Time Ice Cream Parlor, Sylvan Brewing, and Pedal Pushers Cafe while you’re in town. In addition, the Commonweal Theater is a well-known community theater. The name “Lansingboro” is also often used “Minnesota is known as the “Bed and Breakfast Capital of the World,” so if you’re planning a trip there, you may want to look into staying in a B&B. The “heart of Bluff Country” is conveniently located within driving distance of three major cities: Rochester (60 miles), La Crosse (50 miles), and Minneapolis (125 miles).

Winona Lake, Indiana is a hidden treasure located about 2.5 hours from both Indianapolis and Chicago in the state’s northern corner. The historic lakeside district of The Village at Winona has quaint boutiques housed in restored cottages and is listed on the National Register of Historic Places. You should stop at The Olive Branch, LetterWood Paper Co., and The Mucky Duck, and eat at Cerulean or the Boathouse Restaurant. The Lake House rents out paddle boards and kayaks, so you can go out on the lake, or you can swim from the beach at Lake Park, which also offers a splash area for kids.