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.

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.