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Midwest Cities to Visit - Heartland Vacations Skip to content

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Heartland Getaways

Kansas City, Mo.

Jazz Band Horns, Nightclub Kansas City, Heartland Getaways


En español | Kansas City’s barbecue tastes even better with music — and both are top-notch in this city of about 480,000. Most nights you can catch everything from blues to country to jazz, pop and more. Jazz lovers will want to head to the Blue Room in K.C.'s Historic 18th and Vine Jazz District, which swings with live music performed by both up-and-comers and well-seasoned pros. (It's also right next door to the American Jazz Museum.) When you're hungry, there are plenty of restaurants serving good BBQ, but the most popular include Jack Stack BBQ, Oklahoma Joe’s Barbecue and B.B.’s Lawnside BBQ, which offers live blues with its pulled pork every night.


Boats on Canal, Trees and High Rises, Heartland Getaways


Just about a two-hour drive north of Louisville, Ky., and three hours south of Chicago, this capital city of 865,000 has plenty to offer and is easy to navigate: Downtown is within walking distance of the major sports arenas as well as the NCAA Hall of Champions (there are lots of sports lovers here), the adjacent Indiana State Museum for entertaining science exhibitions and the Indianapolis Museum of Art. Also impressive is the Indianapolis Cultural Trail, a wheelchair-accessible eight-mile path that leads away from downtown to six distinct cultural districts with the allure of museums, delicious food and unique shops.



Oriental Theatre Lobby, Milwaukee, Heartland Getaways

Once known mostly for manufacturing and big breweries, this open-hearted city on Lake Michigan is now a “mini-Chicago,” locals like to say; with a population of about 600,000 (compared with the Windy City's 2.7 million), it increasingly provides many of the benefits of that big city just a 90-minute drive south, but for much less money. A short to-do list would need to include the Milwaukee Art Museum; the Historic Third Ward, for art galleries and fun places to grab a bite; and RiverWalk, an urban trail that cuts through the city on both sides of the Milwaukee River. Also fun: brewery tours and the many festivals held throughout the year (the biggie for music is Summerfest).



Music Hall, Cincinnati, Heartland Getaways


A city is never all about one neighborhood, but an old German area in Cincinnati called Over-the-Rhine has managed to turn this town around — encouraging investment and drawing new residents to its gentrified coolness. OTR, as locals call it, is now a vibrant, carefully cultivated 319-acre mix of condos, apartments, restaurants, bars and shops, many in renovated 19th-century brick Italianate buildings. The city of nearly 300,000 is also home to the world-class Cincinnati Symphony Orchestra and Cincinnati Opera, a new Shakespeare Company theater that’s modeled after London’s Globe Theatre, and the Cincinnati Art Museum, established in 1886 and boasting 167,000 works of art.

Louisville, Ky.

African-American Bartender Serves Whiskey Bar, Louisville, Heartland Getaways


You don't have to like the taste of whiskey to fall for Louisville (pop. 253,000), a gem of a destination that offers a wealth of serene parkland with an urban sensibility. Besides distillery visits, tourists head for the lush Cave Hill Cemetery, where Louisville natives Muhammad Ali and Col. Harland Sanders (of Kentucky Fried Chicken fame) are buried, and the Louisville Slugger Museum & Factory to see where the famous bats are born. Hot areas for food and drink include the stylish Butchertown neighborhood and NuLu, short for New Louisville, along downtown’s Market Street. It's home to some of the city’s best farm-to-table restaurants. 

Columbus, Ohio

Short North District Arches, Columbus Ohio, Heartland Getaways


This city of almost 900,000 is the biggest in Ohio and the state capital but is often overlooked as a getaway destination. That’s changing. In recent years it's had an influx of new residents eager for cool restaurants, bars and cultural offerings. Some of the most popular are in the Short North Arts District, full of galleries, boutiques and great spots to eat (the Pearl) and drink (Brothers Drake Meadery). June brings the Columbus Arts Festival, with hundreds of artists exhibiting along the Scioto Mile, a 175-acre greenway connecting downtown to the river.


Visitors Blur, The Last Supper, Warhol Museum, Heartland Getaways


Made rich by the success and philanthropy of men like Andrew Carnegie and Andrew Mellon, Pittsburgh has enjoyed a cultural bounty that’s the envy of many other American cities its size (about 300,000). Music reigns at Heinz Hall, home of the Pittsburgh Symphony Orchestra, and across town at the Carnegie Museum of Art you’ll find masterpieces by Monet, Whistler, Degas and Pollock. On the North Shore, the Andy Warhol Museum offers iconic works from the city’s native son, and the Mattress Factory exhibits a bold array of brilliant experimental and contemporary art. 

Madison, Wis. 

Cheese Shop, Madison, Heartland Getaways


The capital of Wisconsin has the advantage of being a big college town with about 250,000 residents — meaning it’s got lots going on, from Badgers football games to great places to eat, drink and shop. It’s been called a foodie paradise, thanks to places like Fromagination for artisanal cheese and tasty-and-trendy restaurants that include A Pig in a Fur Coat, for pork of all sorts, and the Old Fashioned, a favorite for cheese curds. And there are endless opportunities to play outdoors, with hiking and biking — the Capital City State Trail cuts through the city and on to scenic spots — and no fewer than five lakes in the area.

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