Road Trip

The Ultimate Road Journey Through the Upper Midwest

As I browse through Pinterest, I’ve noticed a prevailing trend when it comes to road trip destinations in the United States. Most of them seem to focus on the Western or Eastern Coasts. However, it’s high time we shine a spotlight on an Upper Midwest road trip.

For those of us who are centrally located in the continental United States, it’s natural to wonder where we can embark on a road trip adventure without spending excessive hours behind the wheel.

After meticulously researching and gathering valuable road trip tips, I’ve carefully crafted the perfect Northern Midwest road trip itinerary for 2023. Don’t forget to print out your free road trip planner before hitting the road!

Milwaukee, Wisconsin

Our Upper Midwest road trip commences in the vibrant city of Milwaukee, situated on the western shore of Lake Michigan. Milwaukee offers a wide range of activities suitable for the entire family.

Our first stop is the Milwaukee Art Museum, renowned worldwide for its rich collection of art, creating a culturally enriching environment. Following this, we’ll visit the Public Market for a delightful lunch, indulging in scrumptious local cuisine that will leave you craving more from this charming eatery.

If your journey aligns with the summer season, consider attending one of the numerous festivals happening throughout the season. Germanfest is a personal favorite, where you can relish brats and beer in a festive atmosphere. Afterwards, take a leisurely stroll along the scenic riverwalk, enjoying the picturesque views or observing kayakers getting their workout on.

After an action-packed day, ensure you get a good night’s rest because the following day takes us to the splendid Twin Cities.

Minneapolis, Minnesota

After a 5-hour drive on our Upper Midwest road trip, we find ourselves in the more famous of the Twin Cities. To fully appreciate this city, we need to head straight downtown.

Our first stop in Minneapolis is Water Power Park, offering stunning views of both St. Anthony Falls and the iconic Stone Arch Bridge along the Mississippi River. Following that, we’ll visit the Aster Café for a charming lunch experience near the park. A perfect next stop is the St. Anthony Falls Visitor Center, where you can learn about the lock and dam system of the great falls. Continue to the Walker Art Center, which welcomes the public with beautiful art installations lining the terrace in the Minneapolis Sculpture Garden.

If you find yourself with free time, take a moment to visit one of Minnesota’s “10,000 Lakes” and soak in the natural beauty.

Medora, North Dakota

While Medora, North Dakota, may not offer a plethora of attractions, there are plenty of interesting stops along the way during our Upper Midwest road trip.

Our first stop on this journey is Frontier Village in Jamestown, North Dakota. Initially, it may not seem like this town has much to offer, but Jamestown boasts the world’s largest buffalo statue. After this intriguing visit, get back on the road and head to your next giant animal encounter, a colossal cow located in North Salem, North Dakota.

Subsequently, embark on the Enchanted Highway, adorned with colossal metal structures. Our final destination is just outside Medora, North Dakota, where Theodore Roosevelt National Park awaits with its scenic overlooks and numerous hiking opportunities. To conclude the day, head over to the Medora Musical and savor a meal at one of Medora’s renowned steak houses.

Deadwood, South Dakota

Four hours south of Medora, North Dakota, our Upper Midwest road trip brings us to the historic town of Deadwood.

Home to legendary gunslingers and gold mines, this stop is a paradise for history enthusiasts. Explore the fascinating Broken Boot Mine, a perfect gold mine to visit. Keep in mind that during the summer, the famous Sturgis motorcycle rally takes place, so if your trip coincides with this event, be prepared for large crowds.

The Lodge at Deadwood is an excellent lodging choice, complete with a charming pool for cooling off, especially if you’re traveling with children.

After immersing ourselves in the history of this town, it’s time to head back east.

Keystone, South Dakota

Our next stop is globally recognizable.

As we journey through the Black Hills on our way from Deadwood, you’ll be treated to the sight of the faces of some of America’s founding fathers carved into a mountain. As one of the top National Parks in the Midwest, Mount Rushmore draws visitors from around the world. While you may encounter numerous fellow tourists exploring Mount Rushmore and its surroundings, there are several pathways to help manage the crowds.

Be vigilant for wildlife, as it’s common to see animals strolling along the paths alongside visitors. Travelers from various corners of the globe gather here, so be sure to have your camera ready to capture the awe-inspiring Mount Rushmore.

After soaking in the wonders of Keystone, it’s time to head further east to Des Moines, Iowa.

Des Moines, Iowa

Following the longest leg of our Upper Midwest road trip, you’re likely to be quite hungry.

A perfect starting point in Des Moines is the renowned Fong’s Pizza. If your trip coincides with the Iowa State Fair, Des Moines is the place to be. Often hailed as the premier state fair to attend, it offers a wide array of delectable food, beverages, and activities to delight you.

If the state fair isn’t your cup of tea, visit the Pappajohn Sculpture Park, a short walk from downtown, where you’ll find a stunning sculpture garden nestled amid natural surroundings. Before heading to your hotel, make a stop at the Greater Des Moines Botanical Garden, where you’ll encounter a delightful array of blooming plants during the summer.

Now, we embark on our final stop—Chicago.

Chicago, Illinois

As the last destination on our Upper Midwest road trip, Chicago is sure to leave a lasting impression.

A five-hour drive from Des Moines, Chicago awaits to help you conclude your incredible road trip. Chicago boasts the renowned Bean, formally known as Cloud Gate, a colossal, mirror-like, bean-shaped sculpture offering the perfect backdrop for your photos.

Next, venture to Buckingham Fountain, where you’ll witness a captivating display of water fountains harmoniously complementing each other. History enthusiasts will find plenty of museums to explore in Chicago, with personal favorites being the Field Museum and the Shedd Museum. However, you can select museums tailored to your interests.

To complete the round trip, we head back up to Milwaukee.

This sequence of cities in the Northern Midwest of the United States has been carefully crafted to offer the ultimate Upper Midwest road trip. Regardless of where you begin this adventure, you’ll ultimately return to your starting point, allowing you to save precious time.

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