The Great Upper Midwest Road Trip

Scrolling on Pinterest, I see one trend with road trips. They all tend to be on the western or East Coast of the United States. Well, its about time we discuss a upper Midwest road trip.

If you are like me, you are located in the smack center of the continental United States and are wondering where you can drive to on a road trip without being in the car for over 20 hours.

With the help of the perfect road trip tips and after hours of research, I have curated the perfect northern Midwest road trip for 2021.

Make sure to print out your free road trip planner before you leave!

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Milwaukee, Wisconsin

Our upper Midwest road trip journey begins in the great city of Milwaukee. Located on the west coast of Lake Michigan, Milwaukee offers activities for everyone in the family.

A great first stop in the Milwaukee Art Museum. Populated with beautiful art, this museum is world-renowned for its culturally-enriched environment. Next, let's check out the Public Market for lunch. Filled with delicious local food, you will be left stuffed yet wanting more from this cute eatery.

If traveling in the summer, your next stop could be at one of the dozen festivals running through the season. One of my favorites in Germanfest where you can enjoy the afternoon eating brats and beer. Afterward, head over to the scenic riverwalk to enjoy the view or join the kayakers getting their workout session in.

Get good rest after this activity-packed day, tomorrow we are heading to the glorious Twin Cities.

Minneapolis, Minnesota

After a 5-hour drive on our upper Midwest road trip, we now find ourselves in the more famous of the two twin cities. To truly enjoy this town, we need to head straight downtown.

A great first stop on this upper Midwest road trip is Water Power Park where you can walk down to the Mississippi River to get amazing views of both St. Anthony Falls and the famous Stone Arch Bridge. Afterward, head over to Aster Café where you can enjoy a quaint lunch near the park. A perfect next stop is St. Anthony Falls Visitor Center.

This is where you can learn about the lock and dam system of the great falls. Next, head over to the Walker Art Center which is open to the public. You will see beautiful art statues along your journey lining the terrace in the Minneapolis Sculpture Garden.

If you have free time be sure to stop at one of the 10,000 lakes Minnesota boasts and the "Land of 10,000 Lakes".

Medora, North Dakota

While there is not much to see in Medora, North Dakota, you will want to make plenty of stops on our upper Midwest road trip along the road there.

The first stop you will want to make is Frontier Village found in Jamestown, North Dakota. At first, you may not believe this town has much to offer, however, Jamestown offers the world's largest buffalo statue. Afterward, get back on the road and head to the next giant animal. This one happens to be a giant cow and is found in North Salem, North Dakota.

Following this stop, make sure to get on the enchanted highway filled with giant metal structures. Our last stop is right outside Medora, North Dakota. Offering scenic overlooks and plenty of hiking options, Theodore Roosevelt National Park is the perfect end to the day.

At the end of the day, head over to the Medora Musical and one of Medora's famous steak houses.

Deadwood, South Dakota

Four hours south of Medora, North Dakota, the next stop along the upper Midwest road trip features the historic town of Deadwood.

Home to gunslingers and gold mines alike, this stop is perfect for history buffs. A perfect gold mine to visit is the Broken Boot Mine. The famous Sturgis motorcycle rally happens in the summer, so if you are planning your trip during this time, be aware you might run into large crowds.

The Lodge at Deadwood is one of the top places to stay. They offer a cute pool for cooling off, especially helpful if you are bringing kids.

After touring this historic town we are heading back east.

Keystone, South Dakota

This next stop is recognizable from around the world.

After cruising through the Black Hills driving from Deadwood, you will be enlightened to see some of the founding fathers' faces carved out of a mountain. As one of the top National Parks in the Midwest, you may see a lot of other guests exploring Mount Rushmore and the surrounding area, however, there are numerous paths to allow for crowd control.

Watch out for wildlife here as it is very common for animals to stroll the paths alongside the visitors. Travelers coming from around the world can be found here. Make sure to bring your camera to document the magnificent Mount Rushmore.

After taking in what Keystone has to offer, we are heading further east to Des Moines, Iowa.

Des Moines, Iowa

After the longest segment of driving the upper Midwest road trip, you are most likely very hungry.

A perfect first stop in Des Moines is the famous Fong's Pizza. If you are lucky enough to travel during the Iowa State Fair, Des Moines is where you want to be. Often noted as the top state fair to visit, food, drinks, and activities are there to fill your happiness.

If the state fair really is not your thing, head on over to the Pappajohn Sculpture Park. A quick walk from downtown, this sculpture garden will surprise you as it is surrounded by nature. On your way out to your hotel, stop at the Greater Des Moines Botanical Garden. Here you will find a beautiful array of plants in full bloom during the summer.

Now we head off to our last stop, Chicago.

Chicago, Illinois

As the last stop on the upper Midwest road trip journey, Chicago will not disappoint.

A five-hour drive from Des Moines, Chicago will be there to help you finish your amazing road trip. Chicago is home to the great Bean (formally known as Cloud Gate). This giant, mirror, bean-shaped sculpture provides the perfect photo spot to document your visit.

Next, head over to Buckingham Fountain where you will see a beautiful display of water fountains complementing each other. For all you history buffs, Chicago offers plenty of museums. My personal favorites are the Field Museum and the Shedd Museum, however, I am sure you can choose ones personalized to your liking.

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


This sequence of cities found in the northern Midwest of the United States has formed the ideal upper Midwest road trip. No matter where you start on this upper Midwest road trip, you will end where you started, therefore allowing saved time.

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