7 Unexpectedly Great Midwestern Cities For a Weekend Visit

It might surprise you to learn that everything you need for a memorable, culture-packed getaway is smack dab in the heart of the Midwest. Sure, there’s plenty of glamour and good eats to be had in a city like New York City or San Francisco, but they’re also more crowded and a helluva a lot more expensive. In cities like Toledo, Minneapolis, and Madison, you’ll find charm in spades alongside hipper offerings like emerging art scenes, cool craft brewers and increasingly renowned restaurants.

Frankly, it’s high time we stop treating the region like “flyover country.” If you’re the sort of person that wants to trade loud, cramped streets for Main Street, USA vibes, you can find yourself in an affordable, easy-to-navigate, mid-sized city bolstered by the laidback congeniality Midwesterners are known for in a few short hours. Weather can run the gamut -- at various times of the year, you’ll experience rain, thundersnow, and polar vortices -- but when you’re hunkering down with stick-to-your-ribs regional specialities (St. Louis-style pizza, Cincinnati chili, and Minneapolis Juicy Lucys, to name a few), you won’t mind too much. After all that beer and food, opportunities abound to work it off, as nature’s never too far out of reach.

Suffice to say, Midwest is best, and these top seven cities prove they’re worth the trip.

The Wisconsin Union
Terrace szn, baby! | The Wisconsin Union

Madison, Wisconsin

This down-to-earth state capital has everything from lakefront views and countless nature trails to beloved cult beers and dedicated farm-to-table food scene

Why go: When it comes to pleasant weekenders with a wealth of things to do, Madison comes out on top. When you add in its walkability, it’s the hands-down winner. There are two ways to do this trip, or combine both options for a trip that has it all. Stay as close to the Capitol building as possible (there are plenty of both hotel and Airbnb options). All the action is right here in the heart of the city, from streets of shops radiating outward from the square -- the Fromagination fine cheese shop and Earthbound Trading Co. are worth a visit -- to Comedy on State, which draws comedy acts from across the nation. Grab a Madison B-cycle in the summer and take a spin around the lake, or plan a trip during the free Frozen Assets winter festival, featuring bike races and kid friendly activities on the lake itself.

Must eat/drink: New Glarus Brewing Company’s current Thumbprint Series brew. Meanwhile, restaurants like Heritage Tavern boast locally sourced -- almost too easy in these farm-filled parts -- and craftily prepared fare, while bars like Camp Trippalindee and Paul’s Club deliver tasty cocktails with a side order of kitsch. Finish up with brunch at Sardine, where French classics -- recent offerings included duck confit with a warm bacon lardon vinaigrette and decadently rich baked creamed eggs -- are lovingly treated and the lakefront views are superb.

Weekend highlights: Camp at New Glarus State Park, which, like all Wisconsin state parks, allows alcohol on-site -- 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.

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 like Southern Rites, a gripping portrait series of Georgia teens attending segregated proms in the 2000s, often highlight the works of university alumni and uphold the reputation of collegiates as forward-thinking provocateurs.

Toledo Museum of Art
Neat! | Toledo Museum of Art

Toledo, Ohio

Family-friendly activities within arms reach of fun-having neighborhoods

Why go: Downtown Toledo is in the midst of a bit 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 it’s also a good spot to spend a night out -- particularly since it was designated open to public drinking, in full Bourbon Street style. Start off at Carlos’ Poco Loco for Cuban staples like succulent ropa vieja and massive (decidedly not Cuban) margaritas, then meander to nearby watering holes like The Attic on Adams.

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 pungent chicken shawarma and lamb-stuffed grape leaves served alongside pizza and spaghetti studded with steak. The Byblos family’s next generation runs the small-plates gem Poco Piatti, which is opening a new downtown location this spring.

Weekend highlights: 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 (just ask Sgt. Maxwell Q. Klinger of M*A*S*H*), and the Minor League team’s downtown ballpark has become the epicenter of Toledo’s entertainment district. Dubbed Hensville, the area around the ballpark offers a summer concert series (catch Diana Ross in July) and great sports bars like Ye Olde Durty Bird and Fleetwood’s Tap Room.

Don’t leave without: A free visit to the Toledo Museum of Art, voted “America’s Favorite Art Museum” by art enthusiasts and acclaimed for its stunning Glass Pavilion. Glimpse familiar sights like Monet’s water lilies alongside modern artists like Chuck Close, while keeping your eyes peeled for temporary exhibits from renowned artists like Kehinde Wiley and Mel Chin. Or cap off your weekend (when the weather is nice) with stop by the Toledo Zoo, a past winner of the Best Zoo in America award, which boasts 10,000 animals in one scenic, sprawling go.

Minneapolis, Minnesota

World-class food scene, artsy jaunts and one heckuva signature burger

Why go: Yes, it’s the farthest north we’ll send you, but oh, is it worth it. Besides its vibrant arts scene, the City of Lakes’ community of chefs tempt both the James Beard crowd and locals alike, making for a cozy getaway.

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 serving up creative charcuterie boards and tempting dishes like mole short-rib chili, a dog-friendly seasonal beer garden and a New Haven-style pizzeria. Of course, you ought to try the city’s best-known delicacy, the 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.

Weekend highlights: Walk off your food baby with a visit to the enchanting Minnehaha Falls -- deemed 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 eager for a glimpse. When you’re ready to hit the town, check out First Avenue for up-and-coming music acts, or go get your culture on at the Guthrie Theater.

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

Quad lawn of University of Illinois
Quad lawn of University of Illinois | Leigh Trail/shutterstock

Urbana-Champaign, Illinois

College-town vibes with plenty of chill hangs

Why go: The quaintest of Big 10 cities, 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. Case in point: swing by Exile on Main Street and the adjoining Daisies Vintage for the type of eclectic records and old-school cool threads you could only find in such an idyllic college town.

Must eat/drink: Don’t skip the Diner Stack -- a mound of hash browns topped with cheese, sausage patties and eggs and smothered in gravy, is found at Merry Ann’s Diner, a classic old-school cool diner that never closes. Black Dog Smoke & Ale House, a spacious and tasty 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 for a two-for-one casual date night.

Weekend highlights: A walk through the University of Illinois campus quad 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 for hours in a college lecture hall. If you care to relive some of those, ahem, fuzzier college memories, there’s a decent college bar scene, but those keeping it classy will have plenty to enjoy, too.

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 stuffed to the gills with historical tomes, children’s books, fiction and every other imaginable genre.

A scrumptious Reuben. | Zingerman’s

Ann Arbor, Michigan

A buzzy Main Street and robust campus life offers a trove of art and culture

Why go: 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 shops like Literati Bookstore and Himalayan Bazaar. Keep heading west until you reach the University of Michigan campus, which is surrounded by blocks of retail, casual eateries and two historic theaters, The State and Michigan Theater. Both are hosts to new movie releases, concerts (Jeffy Tweedy hits up Michigan Theater April 1) and other special events.

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

Weekend highlights: Half the fun of Ann Arbor is found in the nooks and crannies, exhibited by both Nickels Arcade and Kerrytown Market & Shops, where you’ll find spice merchants, Fustini’s Oils & Vinegars and vintage finds. Enjoy a delicious meld of Indian and French cuisine at Dessous, featuring seasonal samosas and mashups like avocado naan and green chile chicken with French-baked rice. It’s perfect for a fancy night out, which could then continue at The Last Word, a lovely cocktail bar with thoughtfully reimagined Prohibition-era sippers.

Don’t leave without: A walk through the University of Michigan Museum of Art, where a spotlight on underrecognized genres like Inuit art and the African diaspora amplifies the museum’s permanent multicultural collections.

The Dark Room
Keith Bowman leads the Young Cats of Jazz w/ Keith Bowman Quartet. | The Dark Room

St. Louis, Missouri

Go for the renowned blues scene, stay for the curious squeaky cheese

Why go: 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 rivertown metropolis. The buzziest restaurant in town is the vegetable-centric Vicia, opened by two expats of the 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.

Must eat/drink: Local favorite Melo’s Pizzeria offers wood oven-fired classics, but its unique specialty pies are where the real fun begins. Keep your eyes peeled for the Sloppy Louie, a take on St. Louis-style pizza, appropriately topped with sausage, pepperoni and the city’s signature Provel cheese, a curious, melty fusion of provolone, Swiss and white cheddar. And hey, while you’re here, might as well drink some beer, right? For a taste of history, Square One Brewery 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.

Weekend highlights: 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 and also home to many of the city’s best cultural attractions. Here, you’ll find the free Saint Louis Art Museum, renowned for its modern collection and pre-Columbian art, and the Saint Louis Zoo, where a pack of eight cheetah cubs recently turned one year old. 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 and Soups.

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.

 Oktoberfest Zinzinnati
The largest Oktoberfest in the United States. | Oktoberfest Zinzinnati

Cincinnati, Ohio

Welcoming neighborhoods entice visitors with grade-A nosh, beer and funtivities

Why go: 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 12-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 luxuriant 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 delicious cocktails on the verdant, romantic patio, where live music often elevates the experience.)

Must eat/drink: Black raspberry chocolate chip ice cream at Graeter’s, the French Pot-frozen treat (it’s a thing) that’s been a staple in Cincinnati since 1868. Rhinegeist is a local favorite for craft beer fans, Sam Adams recently unveiled a spacious new taproom, and Fifty West Brewing Company also 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 Camp Washington Chili for a less corporatized take.

Weekend highlights: 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.

Don’t leave without: Taking a walk along the Ohio River. The city’s new 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.
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