The Midwest Has Awesome Driving Roads In The Last Places You’d Think To Look

I have reached three years with The Autopian, and I’m forever thankful to be a part of this team. I wouldn’t have been able to achieve the dreams I have without this site or you, lovely readers. It was about two months or so ago when I realized that it had been a full three years since I last took a trip out to my little-known slice of driving paradise in Wisconsin.

The last time I was out there was when I first chatted with David and Jason about The Autopian. Admittedly, I had ignored warnings from my former Jalopnik editors and was swimming in the Mississippi River when we had that call. I even have a picture to prove it!

That drive was great, just like the previous runs I’ve done out there since discovering the area in 2019. But I realized that I had never driven those roads in the way I wanted to: In an open-top vehicle of some kind. Instead, when I drove the roads in 2022, I did it in my old 2005 Volkswagen Touareg VR6 with a bad transmission valve body and blown shocks.

The post I wrote after that drive was one of the very first that I wrote for the Autopian. Now, it was time to go back and do it in style.

This time, I had access to a 2025 Polaris Slingshot R. I tested the Slingshot R last year, but for 2025, Polaris updated the model with new looks, a revised interior, and a few tweaks to the powertrain. The Slingshot is now slightly more ridiculous, which I love because it’s not like the 2024 model was tame. I’m going to talk about my time reviewing the 2025 Polaris Slingshot R in a separate piece.

One Of The Best Parts Of Wisconsin And Illinois

According to our internal metrics, the most Autopian readers in a single city live in Chicago. If you’re one of our Chicago readers, you know, just like I do, that driving roads are not what Illinois is known for. Sure, the roads do get much better at the southern tip of the state near the Shawnee National Forest, but that’s a long hike just to find roads.

Our many readers in the Milwaukee region in surrounding areas have the same sort of problem going on. Sure, you could head north into the Upper Peninsula of Michigan, but that’s a long drive. There’s also the Kettle Moraine Scenic Drive (above), which I’ve written about several times over the years, but that gets old pretty quickly.

As it turns out, there are great driving roads only a few hours west of northeastern Illinois and much of eastern Wisconsin. Check out this map:

Now, normally, showing a map of Wisconsin isn’t going to thrill a car enthusiast. Look, I get it. I live out here. But the area highlighted in red on the map is a big deal for us.

[Ed Note: This reminds me of a hidden gem that not nearly enough Michganders talk about: The Allegheny National Forest. That’s in Pennsylvania, yes, but it’s less than five hours away, and it makes for a fantastic weekend outdoors trip, not unlike this one Mercedes is describing. Are any of these “awesome” relative to, say, the famous Angeles Crest here near me? Sure! Maybe not as great for testing the handling of your car, but that’s only part of a road’s charm. -DT].

Twisties And Water

This is the part of Wisconsin, Iowa, and the tiniest parts of Illinois and Minnesota known as the Driftless Area. Driftless Wisconsin describes the region as so:

Crawford and Vernon Counties, and the Kickapoo Valley which runs through them, lie in the heart of the Driftless Area. The Driftless Area includes 24,103 square miles, covering all or part of 57 counties in southwest Wisconsin, southeast Minnesota, northeast Iowa, and a small part of northwest Illinois.

The region’s distinctive terrain is due to its having been bypassed by the last continental glacier. The term “driftless” indicates a lack of glacial drift, the deposits of silt, gravel, and rock that retreating glaciers leave behind.

The Driftless Area geography is characterized by its steep, rugged landscape, and by the largest concentration of cold water streams in the world. The absence of glaciers gave the rivers time to cut deeply into the ancient bedrock and create the distinctive landforms. Karst topography is found throughout the area, characterized by shallow limestone bedrock, caves, sinkholes, springs, and cold streams.

I’ve been exploring the Driftless Area since 2019, and I think I’ve found the best places to visit.

On Memorial Day weekend, I tossed my bag into the Polaris Slingshot R, donned my shades and the helmet as required by Polaris, then set off. Due to where I live in Illinois, much of my drive takes place on historic U.S. Route 20. Because of its 3,365-mile length, Route 20 is the longest signed road in the United States. If you were to drive the whole thing, you’d end up at the road’s terminus in Boston, Massachusetts, or Newport, Oregon.

In my case, I rode Route 20 from the suburbs of Chicago and into vast, flat farms. After about a couple of hours of driving, those farms emptied out into rolling hills. Then, the grades of those hills increased, like the amplitude of waves. The further west you drive, the more these hills grow. Then, you’ll notice them being joined by rock faces, peaks, luscious forests, and important to you as a driver, real curves.

The Appetizer

Once you reach Galena, you can immediately turn off Route 20 and enjoy the territory. These roads are real eye candy and make for great photography. This photo was taken just outside of Galena:

Galena itself is a crazy busy, touristy town:

But consider Galena to be an appetizer. The roads around Galena are often short and slow. So, they’re breathtaking, but not because you’re carving corners.

I continued my drive into Dubuque, where I paid a visit to the National Mississippi River Museum & Aquarium. Now, I did this because I wanted to see some historic riverboats. If you’re not interested in riverboat action, just go on ahead and skip the museum. If you want to do this bypass, take Route 20 to Illinois Route 35. Then take that north to Wisconsin Route 11. Turn left onto Route 11 and take that to U.S. 61/151.

From here on out, this is your adventure. What I like to do is take the highway up a few miles to Dickeyville. Then I’ll ride through the town until I hit Indian Creek Road. From there, I just try my best to stick as close to the Mississippi River as possible.

Endless Roads

If you follow that simple instruction, the state of Wisconsin will handle the rest and deliver breathtaking views and engaging roads. The Driftless Area isn’t a place where there’s any one route to take. You can drive or ride all of the roads in the area for a whole day, and you will not catch everything.

Even better is that this drive is family-friendly. The area is littered with recreation areas and parks. There are also rivers to swim and fish in and small-town America to enjoy. This part of Wisconsin is barren as far as population goes. There are roads where you will be the only vehicle for miles. There will be places where your phone will not connect. There will be places where the pavement disappears. You will even encounter weird little nooks and crannies where the road reduces to a single line and snakes its way to a secret fishing spot on the Mississippi.

I love that. Besides, you don’t need your phone for anything other than taking pictures, anyway. Let the world around you provide the fun.

The amazing thing about the Driftless Area is just the sheer scale of it and the breadth of roads at your disposal. The driving stays great past Prairie du Chien and all the way north, nearly to La Crosse, Wisconsin.

There are great things to see if you like nature, too. The Driftless Area has spectacular hiking, some caves, some waterfalls, and even springs. The wild thing is that despite going out here for over six years, I still haven’t seen the caves and waterfalls. That’s because the driving out there is just that overwhelming.

What I would recommend is doing the opposite of what I do. Don’t try to do a single-day speed run, because you’ll miss so much. Instead, go camping at one of more of the Driftless Area’s picturesque campgrounds and take your time taking everything in. Pass through Glen Haven and have a drink at a bar in the middle of nowhere. Visit Wyalusing and check out one of Wisconsin’s oldest state parks.

Really, if a road looks interesting, just point your car or motorcycle down it and go. Even if the road ends in a dead end, and many of them do, you’ll have a blast. I’ve been told by locals that the area is also great for wildlife watching, especially if your favorite animals are of the avian variety. Sadly, I probably spend too much time banging off rev limiters to really enjoy the wildlife.

I didn’t do much in the way of discovery on this drive. Instead, I pointed the Polaris Slingshot R down roads I’ve been on before. Yet, it was even more than in the past. Being in an open-air vehicle made my old favorite roads feel more tranquil at times and more thrilling at other times. Removing the roof, airbags, and a proper windshield made the experience feel a bit more raw.

The Slingshot was a great little companion for this drive, in part for that reason, but also because it was just a blast to send through the curves out there. It sort of felt like I was driving a go-kart. It was just me, some music, a boldly weird Slingshot, and infinite roads. I got lost in a rhythm of slotting that AR5 manual transmission into the next gear, banging my head to the beat, and hugging the curves.

The great part was that so many of the roads out there have speed limits of around 55 mph, so you’re not forced to take the roads at a crawl. Be responsible, of course, but don’t be afraid to have fun. You’ll certainly watch the locals enjoying their little slice of paradise.

A Fun Drive In Almost Anything

While the Slingshot was my steed of choice for this drive, honestly, it would be great in an old British roadster, a Mazda Miata, a motorcycle, or some other kind of drop-top vehicle. But one thing’s for sure: Having no roof made this so much more fun than previous times I’ve been out there. I might head back out there this weekend for my first time on a motorcycle. Then, maybe I’ll return in a Kei car. The Driftless Area is just that fun. Like a great video game, the replayability is evergreen.

If you do somehow get bored, feel free to try out the roads on the Minnesota side of the Driftless Area. I’ve been out there and in my opinion, they aren’t as good as the Wisconsin side. But you may find them to be fun! Likewise, the intensity of the driving also decreases when you drive south of Dubuque. The roads south of the Driftless Area are still great scenic roads for sure, but the number of twisties goes down dramatically.

I ended up spending my whole day out in the Driftless Area. I left home around 10 a.m. and reached Galena maybe three hours later. I then spent so much time zipping around those roads that I didn’t get back home until after 10 p.m. that night. When I checked the Slingshot’s odometer, I noticed that I managed to put a good 400 miles on the unit, and all of those miles were a real joy.

There’s still so much I have left to see. I still haven’t visited the Ulysses S. Grant Home in Galena. I haven’t done the Trans Wisconsin Adventure Trail, either. I also need to see what beauty can be seen in the far northern ends of Wisconsin.

The Midwest has a reputation for being a terribly boring place to drive, and for the most part, this region has earned the reputation. Most roads in the Midwest are a real snoozefest of straight lines and level ground. But if you know where to look, there’s some real driving to be had out here. So, grab your favorite car, take your spouse, your family, or your friends, and hit the road. Maybe I’ll see you out there.