America’s Heartland: An Epic Midwest Road Trip Itinerary

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A Road Trip Route through America’s Heartland

1—Flew into Chicago, Illinois. Toured a couple days. 2—Drove to Dubuque, Iowa. Continued to Minneapolis, Minnesota. Stayed a day. Also toured St. Paul. 3—Drove to Bayfield, Wisconsin. Toured Apostle Islands National Lakeshore.

4—Drove to Marquette, Michigan. Continued to Munising. Toured Pictured Rocks National Lakeshore. 5—Went to Green Bay, Wisconsin. Continued to Milwaukee. Stayed a day. 6—Drove to South Bend, then to the airport.

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1. Chicago, Illinois

Chicago seemed to be the most logical starting point for an epic road trip through America’s heartland. It was the cheapest and most convenient flight from DC, but it’s also arguably one of the best cities to visit in the US. We were hesitant to fly during the pandemic, but we’d heard that so few people were flying, everything was really spaced out. It’s only a two-hour flight (if that). And it was minus a long day of driving and one more day of touring. …So, we opted to fly in and rent a car.

Note: I’ll be doing a post just for traveling during Coronavirus, so stayed tuned. It’s a whole thing. Seriously. The decision on going at all, and then where to go, was not taken lightly. Please put careful consideration into whether traveling right now is a safe and healthy thing to do, not just for you, but for others as well. A lot of different factors were taken into account for this trip, and I’d be happy to answer any questions folks might have.

Getting Around

Getting From the Airport to Downtown

Chicago’s “L” (short for “elevated train”) goes straight from O’Hare to downtown and is pretty easy to navigate.

• You’ll want to follow airport signs to the CTA (Chicago Transit Authority) and hop on the blue line. It only goes in one direction since O’Hare is the end of the line.
• It takes about 45 minutes to get to the heart of downtown and is way more budget-friendly than a taxi.
• You can purchase tickets at an on-site ticket machine for $5 per person.

Getting Around Chicago

Once in the city, we did a combination of walking and Ubering. Yes, Uber was pricey on 4th of July weekend, but it was incredibly hot, we walked miles upon miles every day, and there was quite a bit of construction going on with the L. (Seems to be fairly standard practice during the pandemic to get as much construction done as humanly possible while everyone is teleworking.)

At any rate, under other circumstances, we probably would have used the L to get around. I’ve never been much of a bus user in the US, so that’s likely a decent, wallet-friendly option as well. Ideally, we would have done a hop-on/hop-off bus like we usually do, but they were all closed down. Big Bus Tours operates in Chicago and I get great deals with them, so check them out for sure.

Chicago Sights

We’ve both been to the city before. So this gave us the opportunity to do all the things we hadn’t done before, all the Instagrammable Chicago spots, and then get some lesser-known sights in (my favorite). We also got together with some travel friends for dinner and drinks and that was an excellent time. A mention that Chicago in the summer is so fun and there were lots of happenings over 4th of July weekend despite Coronavirus. Just a great lake town. Literally a “Great Lake” town and “a great lake town!”

• Cloud Gate	• Offshore Rooftop Bar	• Tribune Tower Artifacts
• Crown Fountain	• Promontory Point	• University of Chicago
• Fountain of Time	• Robie House	• Wabash Arts Corridor

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2. Chicago, Illinois to Minneapolis, Minnesota

After a couple days in the big city, we rented a car in Boystown (the sort of premier neighborhood for gay Chicago) and hit the road. Our final destination for the day would be Minneapolis, by way of Dubuque, Iowa. We saw signs in Galena, Illinois for the home of Ulysses Grant on the way to Dubuque, so decided to make a quick stop. Why not, right? The beauty of a road trip.

They had a little house representing the typical home of the time (i.e., not President Grant’s house) and a little old post office and general store. It was just so insanely American, I couldn’t not include photos. That’s literally an American flag with a white picket fence second photo down. Definitely a good idea for a day trip from Chicago.

Dubuque, Iowa (For-Real-For-Real America’s Heartland)

To formally “check off” the state of Iowa, I made it mandatory that we at least stopped in a town and had lunch, did a little walking around. We also ended up driving through the state for several hours, so… I think we’re okay. Given that we’ll have to head back to the region for more states another time, we can dip back into Iowa… if we want to.

Yes, there were lots of cornfields. Iowa is, like, the very definition of America’s heartland, right? But we also did some driving along the Mississippi River valley that were surprisingly pretty.

We stopped in the tiny Mississippi River town of Dubuque, where almost forty large-scale murals are painted on the historic buildings of downtown. The murals were exceptional. But, while it seems the town may once have been a bustling hub of industry, I’d hate to say that it’s not so much anymore. The downtown buildings are pretty cool, but there are an awful lot of vacancies. It was pretty desolate in general. We moved on, stopping for lunch at a catfish place on the Mississippi River just outside town.

Minneapolis, Minnesota

It took a complete day to drive from Chicago to Minneapolis, but we reserved the entire next day for some Minneapolis exploration. Given the recent state of affairs in the United States, we really didn’t know what to expect arriving in Minneapolis. But in no way, shape, or form, did the city of Minneapolis look like a dumpster fire. It was very much a quintessential, vibrant industrial city of America’s heartland. And a huge music city.

I enjoyed my time there, despite the fact that a lot of places were closed down due to the pandemic. There was a lot to do outdoors. And, if I ever go back, I’d definitely check out some of the art museums—the Walker, the Weisman, and the House of Balls. (Just look at this link, for real.) Things we did do…

• Bob Dylan mural	• Prince star	• Stone Arch Bridge
• Ice cream at Izzy’s (famous!)	• Sidewalk Harp	• Weisman Art Museum exterior
• Minneapolis Sculpture Garden	• Spoonbridge & Cherry

We even had a little extra time, so we drove over to St. Paul (Twin Cities!) where we caught the Cathedral and F. Scott Fitzgerald’s homes—where he was born and where he grew up. (…The Great Gatsby… whoever it is that “can’t quite put [their] finger on it.” You know the one—the Great American Novel. And on our road trip through America’s heartland!) Jaw-droppingly beautiful neighborhood, by the way.

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3. Minneapolis, Minnesota to Bayfield, Wisconsin

Next up was a few hour drive to northern Wisconsin, passing through Duluth, Minnesota. We really wanted to visit a national park way up north on the Canadian border, like Isle Royale or Voyageurs… but then I discovered the Apostle Islands.

Bayfield, Wisconsin & Apostle Islands National Lakeshore

The Apostle Islands National Lakeshore is home to Bayfield, Wisconsin and was hands down one of my favorite stops on this road trip. I can’t even tell you how cute this little baby city is (400-500 people). And it’s gorgeous. That true small-town charm in America’s heartland for. sure.

We went sailing through the islands with Animaashi Sailing and stayed at The Bayfield Inn. They had this awesome rooftop bar overlooking the water. We watched the sunset while listening to a band just below. Truly epic. Bayfield is the perfect place to have a relaxing few days on the lake. I highly recommend. If we had more time, we would have kayaked the sea caves!

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4. Bayfield, Wisconsin to Munising, Michigan

Wouldn’t you know Pictured Rocks National Lakeshore is only a short drive from Apostle Islands? Whereas the Apostle Islands are mainly red sandstone, though, Pictured Rocks are spectacularly multicolored. And the #AdventurePartnerForLife insisted on visiting Michigan’s Upper Peninsula. So, that’s where we headed.

Marquette, Michigan

We stopped in the lakefront town of Marquette on the way. Learned that Northern Michigan University is there, but I can’t for the life of me think what the locals do for a living there in the off-season. There’s not much to it.

I can only imagine that the students spend the winters drinking. Just… seems like the perfect location for a total party school. But what would Global Debauchery know about that kinda thing?

Munising, Michigan & Pictured Rocks National Lakeshore

We arrived in Munising and chilled out for the afternoon. The following day was a full day of touring Pictured Rocks, starting with a cruise of the lakeshore first thing in the morning.

The cruise was excellent. It’s difficult to see rock formations from the shore since you’re literally standing on them and looking out at the water. It’s much, much better to schedule a cruise and see them from the opposite direction, if you know what I mean. We did ours with Pictured Rocks Cruises, right at the Munising City Dock, and had a great time.

There were tons and tons of different rock formations. All different colors from all different rock types and chemical interactions. The water was crazy aquas and greens. You just… wouldn’t think this was a Great Lake. The summer colors are gorgeous, but this would also be the perfect destination for a midwest fall getaway!

We spent the rest of the day driving the length of the park, stopping for a waterfall hike and the Grand Sable Dunes. A super cool thing about these dunes is they have what’s called a “ghost forest.”

Most of the park is jack pine, and right on the coast there are these legit sand dunes. Over time, and with weather erosion, the sand under the forest starts to fall into the dune and the dunes gets windswept further and further back. Eventually, the forest collapses into the sand and the dunes basically eat the trees whole. Leaving only the very tops poking out of the sand.

See photos below (waterfall, creek, ghost forest). You’d hardly know you were standing on top of what was once a whole pine tree forest. Jeff didn’t even know we were there upon arrival and was not at all thrilled with the ghost forest. But I personally was tickled pink with the entire phenomenon.

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5. Munising, Michigan to Milwaukee, Wisconsin

After a couple days of fresh air and “enjoying” nature while hiking in the sweltering heat, we set off for another city break. Enter Milwaukee! With a quick stop in Green Bay.

Nothing much to note in Green Bay because we were only there for a half hour for Lambeau Field. Took some photos and tested out a cheese head in the fan store. You know… what one does in Green Bay.

Milwaukee, Wisconsin

It was my first time in Milwaukee, and I. am. smitten. I’ve heard that Milwaukee is, like… “having a moment.” It’s true. I adored it. Think—cheese, beer, ridiculous Bloody Marys with beer chasers, endless German food. (You know how I like my jaegerschnitzel and goulash.) Lots of revitalized historic buildings on the river, local food markets. I even bought a Milwaukee t-shirt that says, “beer and kitties.” It’s perfect.

Oh, right. You want to know what we did. Cool cool cool. I should mention that, in normal times, we’d probably have had three dinners a day at all different restaurants, too.

• Black Cat Alley	• Milwaukee Public Market (twice)	• Riverwalk
• Brady Street	• North Point Water Tower	• Swing Park
• The Bronze Fonz Statue	• Old World 3rd Street	• Wisconsin Cheese Mart
• Hoan Memorial Bridge	• Pere Marquette Park

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6. Milwaukee, Wisconsin back to Chicago O’Hare

After my fill of Wisconsin beers and ciders and cheese curds (#GlobalDebauchery), it was time to swoop down to South Bend to visit Notre Dame’s campus, with a stop at Indiana Dunes National Park.

South Bend, Indiana & University of Notre Dame

Oof. Ummm… what to say… While Notre Dame’s campus is pretty and super well-manicured, South Bend itself leaves much to be desired. (So sorry, friends from South Bend.) We didn’t stay very long, though. Maybe there was a historic city center we missed?

We drove around campus to find the Basilica of the Sacred Heart, Touchdown Jesus, and First Down Moses before stopping by the bookstore. Which is the most insane university bookstore I’ve ever seen. For the record.

Indiana Dunes National Park

Indiana Dunes is one of the few national parks in the state of Indiana. There’s one other park and then a monument and a trail, I think. Something like that. There are four in total. And not all of them are “parks.”

At any rate, I thought it would be just the coolest thing to go hang out on some legit sand dunes on Lake Michigan. Like… who’da’thunk’it? And, while it’s probably a cool experience in general, that day was just not the day I don’t think. The line to get in was crazy, parking was crazier. There was a whole beach and no one was social distancing or wearing masks. (They didn’t have to at the time.)

It was a small park and, if we had a whole day there, I probably would’ve jumped on a trail or two in the dunes. That seemed like a nice idea. Maybe first thing in the morning or at dusk. That being said, I wouldn’t count this one out. Just… at the end of a road trip and don’t want to be around crowds.

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Our Epic Road Trip through America’s Heartland Concludes

After our Indiana stops, we drove straight to a hotel airport where we got to see the sun set over the city of Chicago in the distance. Not a bad finish at all. Tomorrow morning, we’d catch a flight straight home. Overall, I’m pretty satisfied with our “epic road trip through America’s Heartland.” There were some misses in there, but there were definitely some big hits, too. You wouldn’t know if you didn’t go.

Did you have different experiences in some of our less favorite spots? Do you agree with some of our new favorite spots? Anyone embarking on a stateside road trip themselves? Reach out via my Contact page or leave a comment below. Looking forward to the next adventure, friends!

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