Top 10 Charming Small Towns in the Midwest

Move over, Chicago — the Midwest is also home to some stellar small towns.

Fact checked by Elizabeth MacLennan

The Midwest is a region that really has it all in terms of landscapes, from the gorgeous Great Lakes to striking sand dunes, densely wooded forests, and beyond. The bucolic, wide-open spaces and dynamic cities of America’s heartland are ripe for exploration, as more visitors focus on previously overlooked domestic destinations.

While many travelers will only converge on major destinations like Detroit, Chicago, or Minneapolis, the Midwest’s small towns make for memorable excursions too. With that in mind, we’ve rounded up 10 of the best small towns in the area with less than 11,000 residents. Read on to plan your next Midwestern getaway.

Petoskey, Michigan

This cute waterfront town sits near the “Tip of the Mitt” in the northern reaches of Michigan’s Lower Peninsula. Enjoy the historic downtown, where you’ll find artisanal preserves gem American Spoon, former Hemingway haunt Stafford’s Perry Hotel, and upscale kitchen and bar, Pour. Outdoor activities are also key in the area, as it’s home to the world-class Bay Harbor Golf Club as well as great hiking along the North Country Trail and in the Bear River Valley Recreation Area. Don’t forget to hunt for the famous Petoskey stones at nearby Petoskey State Park. Wine enthusiasts should visit some of the designated wineries along the region’s wine trail, such as Walloon Lake Winery (a well-known lake where Hemingway’s summer cottage was located) and Pond Hill Farm, part of the Tunnel of Trees drive.

Hill City, South Dakota

Hill City‘s population totals just under 900, but this small South Dakota town packs a big punch. A few of its can’t-miss sites include Prairie Berry Winery and Miner Brewing Co. for locally crafted and sourced beverages, the 1880 Train for a two-hour, narrated round-trip journey between Hill City and Keystone, and the family-friendly Palmer Gulch Campground, which holds a number of rodeos over the summer. Hill City is also within driving distance of major South Dakota draws like Custer State Park, Mount Rushmore National Memorial, and Crazy Horse Memorial. The town even makes a lovely jumping off point for checking out two of the state’s best national parks, Wind Cave (about 30 miles away) and Badlands (about 90 miles away).

Kohler, Wisconsin

Located in the heart of the Midwest in Wisconsin, the village of Kohler was one of the nation’s first planned communities — the green spaces here were actually designed by the same landscape architect who created Central Park. However, the crown jewel of Kohler is undoubtedly The American Club, an elegant hotel with Wisconsin’s only AAA Five-Diamond rating. Spend some time relaxing at the Waters Spa or hitting the links at the Whistling Straits or Blackwolf Run golf courses. Kohler is conveniently located about 55 miles from Milwaukee and 145 miles from Chicago, so it’s accessible even to travelers outside the region.

Pella, Iowa

Pella, nicknamed “America’s Dutch Treasure” for its connection to the Netherlands, hosts a legendary tulip festival each spring and a working windmill all year long. Other Dutch-inspired spots include Vander Ploeg Bakery, Ulrich’s Meat Market, Dutch Fix, and Jaarsma Bakery. Drive approximately 11 miles to nearby Leighton for small-batch Gouda cheese from Frisian Farms Cheese House, which even has Gouda cheese curds. Plus, Lake Red Rock, the largest in the state at over 15,000 acres, is just outside of town and offers prime recreational adventure. Pella is located about 177 miles from Omaha and 45 miles from Des Moines, making it a great day trip option or weekend escape.

Medora, North Dakota

Tiny Medora serves as the gateway to Theodore Roosevelt National Park, where the majestic Badlands settle into the Great Plains. To explore by car, take the South Unit’s 48-mile scenic drive, which begins and ends in town. Hiking, horseback riding, camping, and snowshoeing are just some of the activities available in the park, alongside spotting bison and prairie dogs. Medora is also home to a cute children’s park, a thrilling zip line, the interactive Pitchfork Steak Fondue dining experience, and Medora Uncork’d, a cool wine bar.

Fish Creek, Wisconsin

It’s hard to pick just one small town in Door County, Wisconsin (a.k.a. “The Cape Cod of the Midwest”), but Fish Creek is a charming option. Highlights include wine tasting at Lautenbach’s Orchard Country winery and market, dinner and a nightcap at the Whistling Swan, and shopping at Sister Golden. For those who want to experience a traditional fish boil or the famous cherry-stuffed French toast — both Door County delicacies — White Gull Inn is a must. As for outdoor recreation, look no further than nearby Peninsula State Park, home to trails, a lighthouse, and swimming and kayaking galore. Rest your head at Thorp House Inn & Cottages, a quaint choice for accommodations.

Ashland, Nebraska

Halfway between Lincoln and Omaha, Nebraska’s biggest cities, lies the small town of Ashland. Its charming and walkable downtown commercial district makes for a bustling destination, with stops like Salt Creek Mercantile, Postscript, Glacial Till Cider House & Tasting Room, and numerous galleries filled with local art. Aviation fans and history buffs can also check out the nearby Strategic Air Command & Aerospace Museum, which offers a flight simulator experience. Plus, Iron Horse Golf Club is a beautiful course just outside of town, while Eugene T. Mahoney State Park welcomes families and outdoor enthusiasts.

Lanesboro, Minnesota

This charming small town in southeastern Minnesota rests on the bluffs of the winding Root River, a popular tubing destination. Bikers should check out one of the state’s premier pathways, the Root River State Trail. In town, pop into Parkway Market & Coffeehouse, Another Time Ice Cream Parlor, Sylvan Brewing, and Pedal Pushers Cafe. Plus, catch a play at the renowned community theater, the Commonweal. Lanesboro is sometimes called the “Bed and Breakfast Capital of Minnesota,” so if you’re seeking an overnight stay, you may want to aim for that type of lodging. Located just 40 miles from Rochester, 50 miles from La Crosse, and 125 miles from Minneapolis, “the heart of Bluff Country” is an easy small town getaway.

Winona Lake, Indiana

Winona Lake is a northern Indiana gem just a two-and-a-half-hour drive from both Indianapolis and Chicago. The Village at Winona, located along the lake, is on the National Register of Historic Places and filled with old cottages that have been turned into cute shops. Visitors should dine at Cerulean or the Boathouse Restaurant and check out stops like The Olive Branch, LetterWood Paper Co., and The Mucky Duck. Get out on the water with a paddle board or kayak rental from The Lake House, or swim from the beach at Lake Park, which also has a splash pad for kiddos.

Weston, Missouri

While this small town in Missouri is only about 33 miles from Kansas City, it feels worlds away from the hustle and bustle of the metro. Start your day by fueling up at Weston Coffee Roastery before hiking in Lewis and Clark’s footsteps at Weston Bend State Park. Experience a farm tour and cheese tasting at Green Dirt Farm, enjoy local beverages from Jowler Creek Vineyard & Winery and Weston Brewing Company, and rest your head at the historic St. George Hotel. Weston’s cute downtown and prime location make it arguably the best small town in the “Show Me State,” which celebrated its bicentennial in 2021.