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Midwest Road Trip Posted by on Aug 14, 2017 in Culture, Travel

There are some things that are distinctly American – apple pie, baseball games, and road trips. There’s just something about getting in your car and cruising the land of the brave and free that Americans love. We’ve already taken a few road trips here – one on the west coast, another on the east, and one down south. This time, we’re going to take a Midwest road trip.


Downtown Milwaukee. Image by Jim Bauer from flickr.com.

Our first stop is the city of Milwaukee. Located in Wisconsin, it’s known as Brew Town for its famous beer industry. Even the baseball team is called the Brewers here. In addition to sampling the city’s many breweries, you can take a stroll on the beautiful lakefront to visit the Art Museum, War Memorial Center, and more. There are also plenty of festivals going on here throughout the year, including Summerfest – the world’s largest music festival.

Check out the “Streets, Beats & Eats” of Milwaukee.


Midwest Road Trip

A view of the city’s skyline.

Next up is Chicago, the 3rd largest city in the US and the biggest in the Midwest. It’s most famously referred to as the Windy City, although there’s much debate on where the nickname comes from. One of the best things you can do here is take a cruise on the Chicago River to admire the city’s legendary architecture. Chicago is also very much a sports town, with teams in all major sports. The Chicago Cubs just won the World Series last year for the first time since 1908. There are tons of museums here, a great food and music scene, and some very fun nightlife.

See what you can do with “48 Hours in Chicago” in this video.



My hometown!

From Chicago, we head to my hometown of Detroit. It’s known as the Motor City since it’s home to the Big 3 automakers – Ford, GM, and Chrysler. While the decline of Detroit has been very well-documented in recent years, the city has been making a tremendous comeback. There are thriving art, music, food, and sports scenes in the city, so there’s lots to do. There’s even an island – Belle Isle – that is a beautiful state park with plenty of activities on offer. When you’re in Detroit, be sure you try the “Coney Challenge” to sample the city’s famous hot dog.

Take another “Streets, Beats & Eats” tour, this time of Detroit.


Cleveland rocks.

Our final stop on the Midwest road trip is Cleveland. It’s located in northeastern Ohio on the shores of Lake Erie. The city is most famous for its Rock & Roll Hall of Fame, where you can see the clothing, instruments, and much more of famous singers and bands. Cleveland is also home to several museums and a thriving performing arts scene. The city’s NBA team – the Cleveland Cavaliers – has had a lot of success recently. Led by LeBron James, they’ve made it to the last three NBA Finals and won the championship in 2016.

Tour the Rock & Roll Hall of Fame in this short video.


While the Midwest doesn’t get as much attention as the west or east coasts, there’s lots to see and do in this region of the US. Plus, people in the Midwest are known to be very friendly and polite. Get out there and take a Midwest road trip and you’ll surely fall in love with this part of the country.

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About the Author: sasha

Sasha is an English teacher, writer, photographer, and videographer from the great state of Michigan. Upon graduating from Michigan State University, he moved to China and spent 5+ years living, working, studying, and traveling there. He also studied Indonesian Language & Culture in Bali for a year. He and his wife run the travel blog Grateful Gypsies, and they're currently trying the digital nomad lifestyle across Latin America.


  1. priyanga:

    Thank you… it’s really helpful