7 Unexpectedly Great Midwestern Cities for a Weekend Visit

It’s high time we stop calling it “flyover country.”

aerial view of city
Not everyone in the Midwest is a farmer. | f11photo/Shutterstock
Not everyone in the Midwest is a farmer. | f11photo/Shutterstock

America’s Heartland is often written off as farm country. And while this is a big part of the Midwest’s past and present, some of the not-so-sleepy cities like Cincinnati and St. Louis are undergoing a pretty big cultural shift thanks to emerging art scenes, cool craft breweries, and award-winning restaurants that take advantage of the surrounding agriculture and are the definition of farm-to-table dining.

With everything from the Great Lakes to the Ozarks—plus regional specialities like Cincinnati chili and Minneapolis Juicy Lucys—the Midwest really does have it all. Now you just need to know where to discover it. There’s a reason the phrase “Midwest is Best” is a popular one—and these seven cities are proof.

view of Wisconsin's State Capitol
All the action is right around the Capitol building. | youngryand/Shutterstock

Madison, Wisconsin

This down-to-earth state capital has everything from lakefront views and countless nature trails to beloved cult beers and a farm-to-table food scene. Stay as close to the Capitol building as possible—all the action is right here in the heart of the city, with walkable streets radiating outward from the square. Grab tickets for a comedy show at Comedy on State, which draws acts from across the nation. You can take a bike ride around the lake, or if you want to get really outdoorsy, camp at New Glarus State Park, which, like all Wisconsin state parks, allows alcohol on-site—a major plus. It’s also a convenient walk from New Glarus Brewing Company, where one of the country’s largest craft breweries produces perfectly balanced beers like Spotted Cow and Two Women, all sold exclusively in Wisconsin.

Must eat & drink: Restaurants like Heritage Tavern boast locally sourced—almost too easy in these farm-filled parts—and thoughtfully prepared fare, while bars like Camp Trippalindee and Paul’s Club serve up fantastic cocktails with a side order of kitsch. End your stay with brunch at Sardine, where the lakefront views are superb.

Don’t leave without: Visiting the Chazen Museum of Art, the University of Wisconsin’s free art museum. Pieces like the worn, canyon-wrinkled “Ethel Long,” by American painter Arthur Byron Phillips, and an appropriately eerie David Lynch work leave lasting impressions, while string quartets and other music acts fill the galleries on Sunday afternoons. Temporary exhibitions often highlight the works of university alumni.

toledo mural
There’s a cultural renaissance underway in Toledo. | Destination Toledo

Toledo, Ohio

Downtown Toledo is in the midst of a renaissance, with Adams Street looking to make itself known as a cultural corridor. House of Dow vintage shop and Handmade Toledo are overflowing with quirky, colorful finds, but the street is also a good spot to spend a night out—particularly since Bourbon Street-style public drinking is allowed. Start off at Carlos’ Poco Loco for Cuban staples like succulent ropa vieja and massive (and clearly not Cuban) margaritas, then meander to nearby watering holes like The Attic on Adams.

The Toledo Mud Hens have been a point of pride for the Glass City (named for its early history as a blue-collar town of glassmakers) for over a century, and the Minor League team’s downtown ballpark has become the epicenter of Toledo’s entertainment district. Dubbed Hensville, the area around the ballpark puts on a summer concert series and is home to great sports bars like Ye Olde Durty Bird and Fleetwood’s Tap Room.

Must eat & drink: The craveable, Hungarian-style hot dog from Tony Packo’s, Toledo’s signature dish. No restaurant is as admired in Toledo as the long-established Lebanese-Italian Byblos, where you’ll find fragrant chicken shawarma and lamb-stuffed grape leaves served alongside lobster linguine and ravioli. The Byblos family’s next generation also runs tapas spot Poco Piatti, which serves great craft beer and cocktails.

Don’t leave without: A free visit to the Toledo Museum of Art, acclaimed for its stunning Glass Pavilion. Glimpse familiar sights like Monet’s water lilies alongside modern artists like Chuck Close—and keep your eyes peeled for temporary exhibits from renowned artists like Kehinde Wiley and Mel Chin.

Minneapolis downtown skyline
Come for the Jucy Lucy burger, stay for the art and theater. | f11photo/Shutterstock

Minneapolis, Minnesota

Yes, it’s the farthest north we’ll send you, but oh, is it worth it—if anything, just to try the signature Jucy Lucy burger. Besides its vibrant arts scene, the City of Lakes’s community of chefs tempt both the James Beard crowd and locals alike, making for a gastronomically delightful getaway. Walk off your food baby with a visit to the enchanting, 53-foot-high Minnehaha Falls—arguably the state’s most photographed spot—and the surrounding park, or visit the thriving Northeast Minneapolis Arts District, where hundreds of artists and galleries open their studios to visitors. When you’re ready to hit the town, check out First Avenue for up-and-coming music acts, or get your culture fix at the Guthrie Theater.

Must eat & drink: Pick up something (anything) sweet from Rose Street Patisserie, home to one of the world’s top pastry chefs, John Kraus. New Nordic cuisine has blossomed in this Scandinavian-leaning metropolis (early settlers are rumored to have found it quite warm), with the American Swedish Institute’s FIKA Cafe and, on the upscale end, Spoon and Stable. The massive Surly Brewing is home to a beer hall with pretzels and pierogies, as well as a dog-friendly seasonal beer garden and a New Haven-style pizzeria. Of course, you have to try the city’s infamous Juicy (or Jucy) Lucy cheese-stuffed hamburger, but there are two major competitors for the title of creator: Matt’s Bar and the 5-8 Club. Just to be safe, better sample both.

Don’t leave without: Checking out the Minneapolis Sculpture Garden, a sprawling collection of endless curiosities, including an iconic Robert Indiana LOVE sculpture and a Theaster Gates concept piece titled Black Vessel for a Saint.

kids on campus
College town charm means 24/7 diners and great pizza. | Leigh Trail/Shutterstock

Urbana-Champaign, Illinois

Urbana-Champaign (or Champaign-Urbana) is a college town anchored by the hyphenated cities, with enough going on to satisfy a student body of 50,000. Swing by Exile on Main Street for the type of eclectic records you could only find in this kind of town. A walk through the University of Illinois campus is the perfect way to relive the glory days. Make your way to the Japan House and its gardens for tranquil scenery and public tea ceremonies, while concerts at Foellinger Auditorium (past performers range from Father John Misty to Janelle Monáe) are a chance to actually enjoy sitting in a college lecture hall.

Must eat & drink: Don’t skip the Diner Stack—a mound of hash browns topped with cheese, sausage patties and eggs that’s smothered in gravy—found at old-school Merry Ann’s Diner (which never closes). Black Dog Smoke & Ale House, a spacious barbecue joint, has locations in both of the twin cities, while Jupiter’s Pizza provides not only delicious pies, but also some very chill pool tables great for a two-for-one casual date night.

Don’t leave without: Bibliophiles should expect to spend a few hours at Jane Addams Book Shop, which has amassed a collection of 70,000 (very reasonably priced) titles in its 35-year history as an independent bookstore. Wander through three floors of shelf after shelf stocked with historical tomes, children’s books, fiction, and every other imaginable genre.

downtown street Ann Arbor
Everything you could want out of Main Street USA. | Hanson L/Shutterstock

Ann Arbor, Michigan

Downtown Ann Arbor, with all its Main Street USA charm, is a perfect place to start your visit. Wander from hip chains like Fjallraven to local stores like Literati Bookstore and The Himalayan Bazaar. Keep heading west until you reach the University of Michigan campus, which is surrounded by blocks of shops, casual eateries, and two historic theaters: The State Theatre and Michigan Theater, both of which host concerts and new movie releases.

Half the fun of Ann Arbor is found in the nooks and crannies, exhibited by Nickels Arcade and Kerrytown Market & Shops, where you’ll find spice merchants, Fustini’s Oils & Vinegars, and vintage finds. After a day of leisurely wandering, head to The Last Word, a cocktail bar with thoughtfully reimagined Prohibition-era sippers.

Must eat & drink: Everyone will tell you this, but only because it’s true: You must eat at Zingerman’s Deli. The Ann Arbor institution offers dozens and dozens of massive, irresistible subs—a personal favorite is the Aubrey’s Milk & Honey with hot sopressata and homemade goat cheese drizzled with honey and served on rustic Italian bread. An adjoining bakery and artisanal delicatessen offer an epicurean treasure trove of kitchen goodies.

Don’t leave without: A walk through the University of Michigan Museum of Art, where a spotlight on under-recognized genres like Inuit art and the African diaspora amplifies the museum’s permanent collection of Western, Asian, and modern and contemporary art.

Budweiser bottling facility
One of the city’s claims to fame. | RozenskiP/Shutterstock

St. Louis, Missouri

If there are two things St. Louis is known for on a national level, it’s the Gateway Arch and Budweiser. But its flourishing dining and culture scenes are reason enough for a visit to this river town. The buzziest restaurant here is vegetable-focused Vicia, opened by two expats of acclaimed Blue Hill at Stone Barns in New York, but other great picks include Bosnian favorite Lemmons by Grbic (St. Louis has the largest population of Bosnians outside of their home country) and food truck graduate Guerrilla Street Food.
Forest Park—one of the largest urban parks nationwide—clocks in at almost twice the size of Central Park, and it’s a scenic, lagoon-dotted Eden that’s also home to many of the city’s top cultural attractions. Here, you’ll find the free Saint Louis Art Museum, known for its collection of 34,000 objects from 5,000 years of history and different cultures, and the Saint Louis Zoo. Wrap up your night with a visit to the snazzy jazzy club The Dark Room at The Grandel or the laidback BB’s Jazz, Blues & Soups.

Must eat & drink: While you’re here, might as well drink some beer, right? For a taste of history, head to Square One Brewery, which is housed in a century-old former Anheuser-Busch tavern, while Bridge Tap House and Wine Bar provides a thorough introduction to the local scene with 55 beers on tap out of more than 200 total brews to sample.

Don’t leave without: Strolling down Cherokee Street, a vibrant district anchored by antique shops like The Purple Cow and Mesa Home, art galleries, and Latinx-owned bakeries.

Cincinnati river front with steam boat
You’ve got everything from the bourbon to the donut trail here. | RobDun/Shutterstock

Cincinnati, Ohio

Straddling the Ohio River that separates the Buckeye State from Kentucky, this German-settled river city boasts the largest Oktoberfest in the United States, three major sports franchises, and a thriving music scene. In some sense, Cincinnati proves to be a choose-your-own-adventure getaway: Partake in the 13-stop Donut Trail or the winding Kentucky Bourbon Trail, or spend a day stopping by the many breweries.
As a city of neighborhoods, Cincinnati also provides dense pockets of retail and dining options that are fun to explore. O’Bryonsville, Hyde Park, and Oakley are top candidates for an afternoon out (absolutely do not miss out on the double-chip opera cake adorned with buttercream rosettes and a smooth chocolate glaze at The BonBonerie), while Mt. Adams is tailor-made for a night out. Start off at Blind Lemon for cocktails on the lush, romantic patio, where live music often elevates the experience.

The main stretch of Over-the-Rhine has become a hipster mecca of trendy eateries and cool bars like Longfellow (check out its tiny Other Room for the state’s largest selection of rum) and Rosedale, while Fountain Square anchors downtown and offers summertime programming and a winter ice rink.

Must eat & drink: Black raspberry chocolate chip ice cream at Graeter’s, the French Pot-crafted treat that’s been a staple in Cincinnati since 1868. Rhinegeist is a local favorite for craft beer fans, Sam Adams has a newish, spacious taproom, and Fifty West Brewing Company offers kayaking and volleyball to really kick the day into high gear. Of course, no visit is complete without a taste of Cincinnati-style chili, a beanless, cinnamon-tinged version traditionally found atop spaghetti or coney dogs. Skyline Chili is the standard bearer, but Cincinnatians in the know will point you to 24-hour Camp Washington Chili for a less corporatized take.

Don’t leave without: Taking a walk along the Ohio River. The city’s Smale Riverfront Park features a carousel with a hand-carved menagerie and a playground area complete with a rock-climbing canyon, racing slides, and log climbers.

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Ariel Cheung is a senior editor for Modern Luxury Chicago, where she covers the city’s dining scene. She resides in the Bridgeport neighborhood of Chicago, where she is currently resisting the urge to adopt every stray cat that crosses her path.