7 Charming, Under-the-Radar Places to Live in the Midwest

As a lifelong Midwesterner, I’ve sat awkwardly in the middle of the East Coast vs. West Coast debate, corn cob in hand and no stake in the game. The misconception that the Midwest is merely a collection of flyover states has always baffled me. While I’m proudly writing this from my Chicago apartment, I long to be in one of the region’s many incredible small cities and towns—you know, places with a rich past, historical buildings, and real Stars Hollow-vibes. Here are some of my favorite charming places to live in the Midwest. 

Population: 26,594
Median home value: $177,819

My friend Colin puts it best when he says Winona is “where God goes to take a break”. Located on the Mississippi River, Winona has a rich Native American history, its land being of the Dakota Nation—in fact, Winona is named for the daughter of Chief Wapasha. With its robust collection of historical sites and preserved architecture, you’ll feel like you’re stepping into a simpler time, which I think we all could use right about now. Its famous landmark is the Sugar Loaf Bluff, a spot offering plenty of hiking trails for nature adventurers. And it’s a birder’s paradise, with the National Eagle Center and International Owl Center. Talk about something to tweet about (forgive me)!

Population: 36,926
Median home value: $102,906

Beloit is making a comeback. This town, located just north of the border of Wisconsin and Illinois, was a destination for many African-Americans during the Great Migration. Formerly a booming manufacturing town, Beloit’s local developers have invested in preserving and expanding the city’s cultural offerings. Visitors from all over the region trek to Beloit’s downtown for Al Fresco on Grand, a weekly outdoor social event in the picturesque city center that features shopping, drinking, and an unimaginable but totally predictable (and greatly appreciated) collection of cheeses. Give in to the charm of the cheddar. 

Population: 75,130
Median home value: $228,493

When you’re in Iowa City, you’re in Hawkeye territory. Situated along the Iowa River, the home to University of Iowa is much more than your typical college town. The “Athens of the Midwest” boasts creativity and academia, with a Literature Historical Walking Tour, a bustling children’s museum, and countless arts and film festivals. While I’ve only heard the tales (or at least, what they could remember) of the bars and nightlife from my Hawkeye cousins, I know for certain their breweries and restaurants rival what you’d find in any major metropolitan city. “Fight for Iowa!”

Population: 5,529
Median home value: $218,362

Frankenmuth isn’t some sort of freaky monster town (I’ll pause briefly for someone in the comments section to say, “Actually, it’s the monster’s CREATOR’s town!”). It’s considered Michigan’s Little Bavaria, and it shows. Founded by German missionaries, the location was selected in part because it reminded the settlers of their native Bavaria, with rolling hills and the Cass River running through town. If you’re wondering whether to settle there yourself, please keep in mind that 1-800-Fun-Town sincerely, literally, and genuinely is their phone number. Between the Franconian architecture, an epic Oktoberfest, and a strong sense of community, Frankenmuth will charm your lederhosen off. 

Population: 5,916
Median home value: $344,725

Friends, Granville is charming as all heck. The historic Bryn Du Mansion is a massive estate that once hosted Presidents Coolidge, Taft, and Harding. Today, you can view polo matches on the great lawn—or play in them, I suppose, if you’re a professional or a horse. The Granville Inn, built in 1923, features a restaurant and pub for the public, where you’ll certainly want to take in the preserved architecture. And here’s a sentence I never thought I’d write: in the Raccoon Creek valley, prehistoric people built an animal effigy that perhaps depicted a panther or an opossum (who knows?) but it’s called the Alligator Mound. This, and a gorgeous downtown, is all part of Granville’s charm. 

Population: 1,293
Median home value: $224,380

On the western edge of the Midwest lies a rough and tumble town with a history as epic as its rolling hills. A Gold Rush mining town, Deadwood had everything: gamblers, shootouts, Calamity Jane, and a pretty saloon lady who’d drink a rancher under the table and then steal his gun and oxen. Today, there are plenty of attractions that are flavored with the Old West, giving this charming historical town some serious edge. Locals can enjoy the indescribable beauty of South Dakota’s landscape, then mosey down to the rustic town for a drink at one of the town’s wineries and breweries. Yee-haw!

Population: 3,158
Median home value: $193,090

My heart has a fifth chamber, reserved just for Galena. The quintessential town is surrounded by rolling, protective hills, with its achingly perfect Main Street settled at the base, tucked in warmly by the Galena River. Steeped in history, it’s the former home of Ulysses S. Grant, which you can visit, as well as home to the Dowling House, Galena’s oldest preserved house built in 1826. In Galena, you can shop for homemade soaps in a shop with creaking floors and gentle shopkeepers; assume your daily Sun Salutation while covered in goats; course down the slopes of Chestnut Mountain; and dine in a quiet, candlelit tavern amid the low murmur of pleasant diners. With nature and culture as brilliant and bountiful as its starlit sky, Galena’s warmth will win you over.