United States

The Most Charming Towns and Small Cities in the Midwest

by Michael C. Upton  |  Published July 10, 2023

Known for the friendly demeanor of its residents, the American Midwest welcomes visitors to relax in nature, explore history, and relish the cultural aspects of hometowns and small cities.

The American Midwest offers everything from cowboy culture to vibrant art scenes for visitors (Photo: Michael C. Upton for TravelMag)

Towns and small cities offer a specific charm sometimes lost in the major metropolis. The “Heartland of America” was born from agriculture and industry and recently embraced tourists from all over the world looking to explore its natural beauty and charm. The Midwest, an area of almost a million square miles, is larger than the country of Mexico and includes a range of geography from miles of flat corn fields to pristine, lakeside forests. The US Bureau of Labor and Statistics defines the Midwest as including 12 states: Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Missouri, Nebraska, North Dakota, Ohio, South Dakota and Wisconsin.

TravelMag asked more than 100 travel writers, photographers and industry professionals to name up to five destinations in the Midwest they found the “most charming.” The survey only considered locales with a population of under 100,000 residents and our methodology also assures the inclusion of at least one location from each Midwestern state, with a cap of three destinations. Below, in alphabetical order by state, we share the top 20 voted towns and small cities in the Midwest, which provide natural or urban charm, modern or historic significance, and an array of unique options when it comes to dining, entertainment and lodging.

Elmhurst, Illinois

Tree-lined downtown Elmhurst, Illinois offers shopping, dining and entertainment (Photo: David Wilson via Flickr / CC BY 2.0)

The Potawatomi people were the first-known inhabitants of what is now the suburb of Elmhurst, six miles west of Chicago’s Loop. The area is a draw for architecture lovers, since several residential homes were built by famed architects like Mies van der Rohe, Frank Lloyd Wright and Walter Burley Griffin. Elmhurst has several shopping districts, which attract visitors year-round, and a number of museums like the Elmhurst Art Museum. Getting around the vibrant, tree-lined community with thriving retail shops, fine dining and outstanding theater is easy via the free Explore Elmhurst Express Trolley.

Galena, Illinois

The beautifully preserved Galena Historic District is a site to see (Photo: Dirk DBQ via Flickr / CC BY 2.0)

Charming Galena, Illinois boasts a rich history and unique attractions set among stunning 19th-century architecture, including the beautifully preserved Galena Historic District. Many tourists make their way to Galena to visit the Ulysses S. Grant Home State Historic Site, which offers a fascinating glimpse into the life of the Civil War general and former president. Galena’s food scene is a culinary adventure in a small town with an impressive array of restaurants and specialty shops, including the famous fudge from the Great American Popcorn Company. Spirited travelers will enjoy the local wines at Galena Cellars Vineyard & Winery or Massbach Ridge Winery.

Bloomington, Indiana

Bloomington, Indiana is called the Gateway to Scenic Southern Indiana (Photo: Visit Bloomington)

Often called the “Gateway to Scenic Southern Indiana,” Bloomington was established and named by settlers from Kentucky, Tennessee, the Carolinas and Virginia who made their way to the area in 1818. Hoosier pride runs deep here in the home of Indiana University, which adds 40,000 students to the city’s population. Walkable Downtown Bloomington is a blast from the past fast-forwarded to the modern with lively nightlife, museums and galleries, and an ethnically diverse culinary scene. Pizza lovers rejoice in the option of almost 30 places to find a pie, probably thanks to the presence of so many college students.

Columbus, Indiana

Downtown Columbus, Indiana is home to dozens of restaurants, cafés and boutique shops (Photo: Don Nissen / Columbus Visitors Center)

Downtown Columbus is home to dozens of restaurants, cafés, and boutique shops including the nationally recognized ZwanzigZ Pizza & Brewery, which offers 22 craft beers and house-made sodas. History lovers will enjoy a stay at the Inn at Irwin Gardens, a circa-1910 mansion transformed into a posh bed and breakfast; the gardens are open to the public on Tuesday and Sunday afternoons June through October. Pickers enjoy the antique shops off Interstate 65’s exit 76. Columbus has been hailed as a “small-town architectural mecca” and “one of the world’s best cities for architecture lovers.” The Columbus Area Visitors Center offers information on various architectural tours.

Nashville, Indiana

The art scene in Nashville, Indiana attracts visitors (Photo: Brown County Convention and Visitors Bureau)

The people in Nashville love their area and they could not be happier when folks come to visit their slice of the Midwest. The grand draw to Nashville is the art scene. As the center of the Brown County Art Colony, downtown Nashville is home to several galleries, public art exhibitions, and the Brown County Art Gallery with a massive permanent collection of works by early Indiana artists. Visitors enjoy the unique lodging in the area from cabins in the woods to downtown bed and breakfasts and inns. The Historic Brown County Playhouse offers a full slate of entertainment, from concerts to comedy.

Iowa City, Iowa

Year-round, Iowa City is bustling with activity, whether fans of University of Iowa sports or festival goers in the summer (Photo: Michael C. Upton for TravelMag)

In the spring, the scent from flowering trees fills the streets of Iowa City as students from the University of Iowa prepare to depart for the summer. Meanwhile, the 74,596 permanent residents of the crowning jewel of Midwestern small cities prepare for a new season of festivals. Iowa City hosts one of the longest-running Pride festivals in the U.S., a downtown block party which brings in 45,000 visitors. They revel in jazz and art festivals throughout the summer. Iowa City is one of only two U.S. cities to carry the UNESCO designation “City of Literature,” celebrating the written word through workshops, live performances, and markers and murals throughout downtown, especially on the Iowa Avenue Literary Walk.

Dodge City, Kansas

Dodge City, Kansas is an original Midwest cow town (Photo: Visit Dodge City)

Built on the Santa Fe Trail in the 1800s, Dodge City has grown from a cow town of the wild Midwest to an important destination for history-loving travelers. The tourist-friendly town captures the essence of early America with attractions like the Boot Hill Museum, where daily gunfights reenact the wild west; “rough and rowdy” tours aboard the Historic Trolley; and the Long Branch Variety Show. Dodge City Days—attracting more than 100,000 visitors as the state’s second largest annual festival—started in 1960, and the 10-day summer festival celebrates the city’s western heritage with a parade, BBQ events, a classic car show, concerts and much more.

Frankenmuth, Michigan

Fireworks along the bridge in Frankenmuth, Michigan (Photo: Aaron Burden via Unsplash / CC BY 2.0)

Strolling the streets of Frankenmuth, filled with quaint shops and lively eateries, visitors are transported to Michigan’s “Little Bavaria.” German settlers founded the settlement in the mid-1800s and even today families of German descendants make up nearly half of the 5,193 residents. Visitors enjoy the Bavarian architecture and the safe, clean environment. Frankenmuth is home to Bronner’s Christmas Wonderland, and the company offers the largest selection of Christmas ornaments in the world. Bring an appetite as Zehnder’s and the Bavarian Inn Restaurant are famous for serving more than 2 million family-style chicken dinners every year.

Holland, Michigan

Sailboats pass by the Big Red Lighthouse in Holland, Michigan (Photo: Mike Lozon / Holland Area CVB)

In 1847, Dutch immigrants landed in the New World and established what would become today’s Holland, Michigan. The area prospered with different industries, from furniture to pickles, and eventually grew into a destination attracting travel enthusiasts, tulip lovers and amateur and professional photographers who recognize the beauty of the Big Red Lighthouse and the De Zwaan windmill. From its “All-American” downtown to nearby beaches along Lake Michigan, Holland offers everyday delights and annual events beyond its famed Tulip Time. The “Handcrafted Passport” features breweries, wineries, distilleries and cideries in the greater Holland area in an easy-to-use tool.

Marquette, Michigan

Lake Superior serves as a picturesque backdrop to downtown Marquette, Michigan (Photo: Travel Marquette)

In Michigan’s Upper Peninsula, on the shores of Lake Superior, sits the city of Marquette. Vacationers are drawn to the area for its natural beauty, which includes an untouched shoreline in Presque Isle Park and an abundance of hiking opportunities in and around the city. Sustainability is at the forefront of city efforts to maintain the natural wonder of the area. Family-friendly beaches include McCarty’s Cove and South Beach. Beer lovers visit the city’s breweries, taprooms and a fall beer festival, as well as Honorable Distillery, Marquette’s first spirits maker. The city’s Tourist Park has been home to the Hiawatha Music Festival since 1980.

Branson, Missouri

Free trolley service shuttles visitors through Branson, Missouri’s quaint downtown (Photo: Michael C. Upton for TravelMag)

To properly enjoy Branson, out-of-towners must take the advice of previous visitors and “lean into the experience.” Although a tourist destination attracting millions of guests each year, Branson’s charm is in the locals who love their little neck of the woods like no other. A visit to the Branson Centennial Museum downtown displays a history of the town apart from the mega-attractions lining Country Boulevard. A visit to the College of the Ozarks allows guests to observe “Hard Work U” students creating stained glass, handwoven baskets, and dry goods. Dining at the student-run Keeter Center is Branson’s finest and the ice cream comes straight from the on-campus dairy.

Saint Charles, Missouri

Winter holidays are a great time to visit St. Charles, Missouri (Photo: Heath Cajandig via Flickr / CC BY 2.0)

Saint Charles, Missouri was founded as Les Petites Cotes back in 1769. The area just west of St. Louis is steeped in rich history, best experienced by a stroll down Main Street, or a visit to the First Missouri State Capitol State Historic Site or The Lewis and Clark Boathouse. History and culture are celebrated with numerous events throughout the year like the Festival of the Little Hills which showcases local art, music, food, and traditions passed down through generations. The unique blend of old-world charm and modern amenities make Saint Charles an ideal destination for travelers seeking an authentic Show Me State experience.

Lanesboro, Minnesota

The 42-mile Root River State Bike Trail is a major draw to Lanesboro, Minnesota (credit Ryan Taylor)

Called a hidden gem of Minnesota, Lanesboro is a blend of art, agriculture and outdoor recreation. Many visitors come to Lanesboro via bicycle from the Root River State Bike Trail, which runs 42 miles from Fountain to Houston with Lanesboro in the center. The “Bed & Breakfast Capital of Minnesota” is home to a vibrant arts center, a professional theatre and eclectic shops for fun and unique gifts. Seasonal festivals include the Rhubarb Fest, Art in the Park and Buffalo Bill Days. Foodies will enjoy the elevated fast casual cuisine at Juniper’s.

Grand Forks, North Dakota

The Japanese Gardens make a relaxing place to stroll while visiting Grand Forks, North Dakota (Photo: North Dakota Tourism / Greater Grand Forks Visitor’s Bureau)

Space may be the final frontier, but in Grand Forks it is just the beginning. Home to the University of North Dakota and their research center for aerospace science, this small city of 60,000 residents on the border of Minnesota boasts an eclectic public art scene, a variety of locally owned shops, and a handful of breweries, like the fun and funky Rhombus Guys Brewing Co. Apart from activities on the Red River, popular draws include the Sertoma Park Japanese Garden, the “World’s Smallest Art Gallery” at Urban Stampede coffee shop, and Widman’s Candy Shop, home of chocolate-covered potato chips.

Valentine, Nebraska

Kayaking, tubing, and canoeing on the Niobrara River brings visitors to Valentine, Nebraska (Photo: Jeffrey Hamilton via Unsplash / CC BY 2.0)

The sleepy Midwestern town of Valentine, Nebraska is actually a hidden gem for adventure enthusiasts and home to some of the most stunning natural attractions in the United States, including the famous Niobrara River and its surrounding sandstone cliffs. Visitors can explore the river by kayaking, tubing, or canoeing. For those who prefer hiking, the nearby Fort Niobrara National Wildlife Refuge offers miles of scenic trails that wind through rolling hills and prairies. Valentine is cowboy country, and Bolo Beer Co. invites brewery visitors to “go western” and meat eaters will enjoy stops at Bordertown Steakhouse and Bulldoggers BBQ.

Lancaster, Ohio

Downtown Lancaster, Ohio is filled with activity as people gather (Photo: ReineDownPhotography)

First organized in 1800 and settled by German immigrants from neighboring Pennsylvania, Lancaster predates the state of Ohio. Modern Lancaster is dedicated to historic preservation and has embraced the nationally recognized Main Street America program. Fueled by an abundance of natural gas, glassmaking has become a part of life in this city of 40,763 residents 30 miles southeast of Columbus and visitors flock to the city’s Ohio Glass Museum. Sightseers enjoy the downtown covered bridges, the buzz of the open-air art trail, and an annual 10-day music and arts festival in the summer. The Glass City and surrounding Fairfield County is home to several wineries and breweries.

Yellow Springs, Ohio

Beers and bikes are popular pastimes for visitors and residents of Yellow Springs, Ohio (Photo: Greene County CVB)

Twenty miles west of Dayton, Ohio sits the Village of Yellow Springs, a new hot spot for travelers looking for an authentic, small-town atmosphere. With more than 50 shops specializing in books, artwork, pottery, jewelry, stained glass and more, Yellow Springs attracts visitors looking for unique items and gifts. The village of less than 4,000 residents is home to eight restaurants ranging from creative, four-star dining at the Wind’s Café—with items like a duck sausage corn dog and almond-crusted walleye when in season—to the casual and historic Olde Trail Tavern. The 28-room boutique Mills Park Hotel is a prime reservation.

Deadwood, South Dakota

Travel back in time to the historic city of Deadwood, South Dakota
(Photo: Travel South Dakota)

Deadwood is a rare gem in that the entire town is a National Historic Landmark. Travel back to 1876 when historic folks like Wild Bill Hickok and Calamity Jane roamed these cobblestone streets through Wild West reenactments happening daily over the summer months. Today, Deadwood embraces a touch of the modern with 1,700 contemporary hotel rooms, winery tasting rooms and major entertainment events like concerts, rodeos and parades. The 24-hour gambling is nothing new! Every building, street and hillside holds a legendary story and a great way to learn the history of this Wild West town is through a guided tour.

Oshkosh, Wisconsin

Greetings from Oshkosh, Wisconsin, an art-filled destination (Photo: Jim Koepnick / Discover Oshkosh)

Snap a selfie in Oshkosh, one of the most scenic small cities in Wisconsin with its system of surrounding lakes offering waterfront dining, Oshkosh Riverwalk scenic walkway, and English estate-inspired Paine Art Center and Gardens. Enjoy arts and leisure at the circa-1883 Grand Oshkosh or the 33,000 sq. ft. Old English/Tudor Revival-style landmark, The Howard, which now doubles as an event space and upscale bowling venue. The Oshkosh Craft Pass allows beer and wine lovers to check in at participating spots to collect prizes like a themed bottle opener or an Oshkosh baseball hat. Oshkosh Craft Beer Week takes place over 10 days in the spring.

Washington Island, Wisconsin

Passage to Washington Island, Wisconsin is through Death’s Door, the strait linking Lake Michigan and Green Bay (Photo: Michael C. Upton for TravelMag)

The 660 Washington Island residents can see the visitors coming. Hopping the ferry from mainland Door County, tourists cross the “Death’s Door” passage between Green Bay and Lake Michigan to arrive on the shores of Wisconsin’s natural and cultural wonder. The island is home to unique spots like Fragrant Isle lavender farm, a Nordic-style church, the pebble-filled Schoolhouse Beach, and Nelsen’s Hall—home of the Bitters Club, where entry is a shot of Angostura bitters first embraced as a loophole to prohibition. New events like the Sól Grass Music Festival bring music lovers to the island for a two-day bluegrass event.