Located on the state's western border near the confluence of the Missouri and Kansas Rivers, Kansas City is definitely a must-see city on a road trip through the Midwest. Not to be confused its namesake city just across the border in Kansas, this Kansas City is the largest city in Missouri and best known for its jazz music and BBQ food, as well as its professional sports teams. Depending upon the amount of time being spent here, travelers can choose from several major attractions, including the National World War I Museum and Memorial, American Jazz Museum, the Nelson Atkins Museum of Art — recently named America's best museum by Yelp — and the enormous Truman Sports Complex, featuring Arrowhead Stadium, the home field of the Kansas City Chiefs and Kauffman Stadium, the home of the Kansas Royals. Dining choices abound in the city nicknamed the BBQ Capital of the World and Jazz Capital of the World. Among the favorite dining places are Q39, the Farmhouse, Beer Kitchen, Arthur Bryant's and Joe's Kansas City Bar-B-Que, named one of America's 20 most iconic food destinations by the Smithsonian. Other optional stops worth a visit before leaving the Greater Kansas City area are noteworthy side trips to the Money Museum, Negro Leagues Baseball Museum and the Harry S. Truman Presidential Library & Museum just east of the city in Independence.
After driving for about four hours, the next must-see stop through the Midwest is St. Louis. One of the great cities that resides along the Mississippi River, St. Louis was established in 1764 and named after King Louis IX of France. This great Midwestern city is best known for its world-famous attractions, including the iconic Gateway Arch, known as the Gateway to the West and the world's tallest arch with a tramway to the top; Busch Stadium, home of the St. Louis Cardinals; and the landmark Anheuser-Busch Brewery, known for its best selling beer and its beloved Budweiser Clydesdales. While those are the most high profile attractions in the city, visitors might also enjoy stopping by places like the renowned Missouri Botanical Garden, the oldest in the country, St. Louis Zoo, Ballpark Village next to Busch Stadium and the Missouri History Museum. For dining, road trippers might want to try some local culinary specialties like toasted ravioli, St. Louis-style BBQ or St. Louis-style pizza. Among the best restaurants to consider during a tour of downtown St. Louis are Monty's Sandwich Company, Pickles Deli, St. Louis Bread Company (Panera Bread) and Budweiser Brew House.
Related: Best BBQ Cities In America
Shortly after departing St. Louis, motorists will enter Illinois via U.S. Interstate Highway 70. At this point, travelers can opt to head north towards Springfield or east, crossing the Indiana state line to Indianapolis. Before exploring the must-see downtown area, visitors should definitely stop by the most famous attraction in the Hoosier State, the Indianapolis Motor Speedway, home to one of the most celebrated racing events in the world, the Indianapolis 500. Also known as the Brickyard, the Motor Speedway is the world's largest capacity sports venue, with more than 250,000 permanent seats for racing fans. In addition to a grounds tour of the legendary track and a visit to the Hall of Fame Museum, travelers might also want to make stops at the Soldiers Sailors Monument on Monument Circle in downtown Indianapolis, in addition to other prominent attractions like the Indianapolis Museum of Art, Lucas Oil Stadium, the home field of the Indianapolis Colts, the Indiana State Fairgrounds and, if children are along for the ride, the must-see Children's Museum of Indianapolis. To get the true Indianapolis experience, visitors should opt for delicious local dishes such as pork tenderloin, sandwiches, corn on the cob, pizza sticks with cheese sauce and sugar cream pie, also known as Hoosier Pie. Among the many great Indianapolis restaurants worth checking out are the Eagle, Goose the Market, Paradise Bakery and Cafe, King David Dogs and Giorgio's Pizza.
After leaving the city nicknamed the Crossroads of America, the next major stop is Chicago. The third largest city in the country and largest in the Midwest, Chicago is likely to be the most interesting stop on this lengthy road trip, especially for first-time visitors. That's because there are so many things to see and do, from towering skyscrapers like the Willis Tower, the nation's second tallest building, to historic Wrigley Field, the second oldest baseball stadium in Major League Baseball. The Windy City is also well known for serving phenomenal local cuisine like Chicago-style deep dish pizza, Italian beef, Chicago-style hot dogs and chicken Vesuvio. In addition to Wrigley Field and Willis Tower, other recommended attractions to visit are Navy Pier on the shoreline of Lake Michigan, Millennium Park, Field Museum and the Art Institute of Chicago, just steps from the beginning of historic Route 66. The list of outstanding local restaurants is unsurprisingly extensive, but among the best for the entertaining road trip are Gino's East, Giordano's, Uno Pizzeria, Original Jimmy's Red Hots and Lou Mitchell's.
The final must-see stop on this unforgettable road trip is Milwaukee. While Madison is an exceptionally nice alternative, especially since it's the state capital, a trip to Milwaukee will provide a much more scenic journey from Chicago via U.S. Interstate 94 as it travels near the Lake Michigan shoreline. And as the largest city in Wisconsin. Milwaukee is an incredibly vibrant city known for several famous breweries, extraordinary cuisine and its Milwaukee Brewers baseball team, whose home field is Miller Park. But there are many other noteworthy attractions of particular interest to road trippers. Among the best are the Harley-Davidson Museum, whose corporate headquarters is in Milwaukee, the magnificent Pabst Mansion, Milwaukee RiverWalk, the Bradley Center, Allen Bradley Clocktower and a brewery tour at places like Miller Brewing, Milwaukee Brewing Company and Lakefront Brewery, named TripAdvisor's fourth best brewery tour in the country. Also known as Brew City, Milwaukee is well known for an assortment of food specialties such as pretzel rolls, bratwurst, beer cheese soup, fried cheese curds, chili and butter burger. Travelers can celebrate their end of the road trip at popular restaurants like Smoke Shack, Buckley's, the Wicked Hop, Milwaukee Ale House and Harley-Davidson's MOTOR Bar & Restaurant.
Related: A 48-Hour Guide To Chicago
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