Home » Here Are Three Roads In The Midwest That Are Genuinely Worth Driving

Here Are Three Roads In The Midwest That Are Genuinely Worth Driving


If you’re a resident of the Midwest then chances are you’re well aware that our roads sort of suck. I mean, our potholes can swallow a Smart whole and a “scenic” drive usually consists of long, straight roads dotted by endless cornfields. But what if I told you that you could drive down some engaging and beautiful roads among the farms of Wisconsin, Iowa, and Illinois? If you know where to look, there’s some real good driving to be had out here.

One of my favorite things to do in both a car or on a motorcycle is just go on a random drive. Over the years I’ve found that driving a car or riding a motorcycle is the perfect counter to a rough day or hearing bad news. It’s just the open road, a soundtrack, and your vehicle soothing your soul. But living in the Midwest does come at a cost for this activity. Not only is the world outside frozen for months, but there often isn’t much in the way of scenic or engaging roads. There are farms to my west, suburbs and cities to my east and south, and more farms to the north.

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However, a few years ago I discovered three places in Illinois and Wisconsin that almost make you forget that you’re in the Midwest.

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Photo Credit: Mercedes Streeter

The first is the Kettle Moraine Scenic Drive. This route runs along the eastern side of Wisconsin. If you start up north, the start point is the Broughton Sheboygan Marsh Park in Sheboygan County. This is an active place with spots to camp, launch a fishing boat, and connects to a massive county trail system.

If you start down south like I do, your start point is the southern side of the Kettle Moraine State Forest. The activities here are vast from swimming, watching wildlife, hiking, camping and so much more. It’s easy to get lost taking in either start point, but trust me, don’t spend too much time because there are sights to see! Here’s a handy set of directions and a map.

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Photo Credit: Mercedes Streeter

If you come from the south, one of your first stops will be the village of Palmyra. It’s a true tiny American town where if you blink you’ll miss it. Palmyra is one of those places where the town’s major upcoming events are displayed on a sign. The highlight of the town is Blue Spring Lake, a mineral spring with some wonderful water to swim, boat and fish in.

A little up the town’s main street is Spring Lake, a place where I’ve gotten in a relaxing swim after a hot motorcycle ride.

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Photo Credit: Mercedes Streeter

Once you’ve gotten your watery fill, continue to follow the Kettle Moraine Scenic Drive’s route to find some truly gorgeous parts of Wisconsin that you may not have known existed. You’ll ride or drive through twisting turns, tall forests, and pass through countless little towns. The route runs along the Kettle Moraine State Forest, so you’ll find plenty of places to stop to get out on foot and experience nature.

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Photo Credit: Mercedes Streeter

If you came from the south, the roads will get progressively more curvy the farther you drive. At times it’ll feel like a miniaturized version of the Tail of the Dragon, and on weekends you’ll catch car and motorcycle clubs riding around the curves. One particular area of interest will be the Greenbush Recreation Area. The speeds are low, but the turns and the scenery make it so worth it. Sadly, I couldn’t safely stop for pictures here as there isn’t a shoulder. Amazingly, not even Google has gone back there.

Overall, the Kettle Moraine Scenic Drive is 114.5 miles of a drive that should make any day a good one. I’ve done this drive a number of times and still haven’t seen everything.

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Photo Credit: Mercedes Streeter

If you like your trips a lot more unguided, there is a huge swath of Wisconsin, Illinois, Iowa, and Minnesota out west offering roads that would feel at home nestled in Tennessee’s mountains. It’s called the Driftless Area. Driftless means that the terrain in the area hasn’t seen glacial drift, or the deposits of silt, gravel, and rock left behind by glaciers.

The Area covers some 24,103 square miles of all three states, but the best of it for vehicle enthusiasts is around the Galena, Illinois area and north along the Mississippi River.

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Photo Credit: Mercedes Streeter

The area is characterized with steep hills, forests, rocky ridges, river valleys, waterfalls and even cave systems. There are no specific routes to drive out here, but I recommend sticking close to the Mississippi. That’ll give you an experience that you will remember. On the Wisconsin side you’ll encounter long, sweeping turns, steep hills, and even switchbacks.

A lot of roads out there are unpaved with speeds up to 55 mph. Some of these roads are little adventures of their own. Check out this dirt side road between the small town of Bagley and the even smaller town of Glen Haven.

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Photo Credit: Mercedes Streeter

The road follows along the Mississippi and a set of railroad tracks. It also glances by the Devil’s Backbone State Natural Area.


You’ll rarely have cellular reception out here, but that only amplifies your experience. You’ll stop at an intersection and find yourself stuck at the decision to go right, go left, or keep straight.

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Photo Credit: Mercedes Streeter

That’s how wonderful these roads are.

Admittedly, these roads aren’t as grand as California’s Pacific Coast Highway or the Blue Ridge Parkway, but a Midwestern resident won’t have to drive 2,000 miles to experience them, either. In my three years of visiting this area I’ve yet to cover all of the roads and it still hasn’t gotten old.

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Photo Credit: Mercedes Streeter

If you drive far enough north, be sure to visit Wyalusing. There, you can take a dip in the Mississippi without getting washed away then later visit the area’s State Park.

And if you drive across the border, I highly recommend a visit to the National Mississippi River Museum in Dubuque. After, you could take a riverboat cruise while you’re there. In Galena, you can also see the Ulysses S. Grant Home.

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Photo Credit: Mercedes Streeter


Amazingly, there’s still one more route to go, and it’s one that I’ve yet to go on. For the off-roaders out there, Wisconsin offers the Trans Wisconsin Adventure Trail. The TWAT offers some 600 miles of adventure with a mix of pavement, gravel, dirt, and sand. The TWAT itself shouldn’t require any hardcore off-roading equipment and it could even be done on motorcycle. But the route does have ATV trails for those who really want to go wheeling. The TWAT is also a longer journey than the other two, taking two to three days to complete.

[Editor’s Note: Uh. – JT]

I hope to cover the TWAT this year from the saddle of my Triumph Tiger. Until then, I’m more than happy to continue exploring the Driftless Area. And if you live out here or are simply passing through, I highly recommend that you do, too. The Midwest usually has boring roads, but these are anything but!

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2 years ago

I have completed the TWAT 3 times and I recognize many of your photos from the route. Thanks for highlighting that!


Also, spot-on with the Driftless Region. I dont think people in the Chicago-area or elsewhere in the prairie understand how great this area really is. I have tons of routes mapped out for day trips or longer in the area from work I have done. If anyone wants some more travel advice for the area, please let me know.

Doug Kretzmann
Doug Kretzmann
2 years ago

I borrowed my son’s WRX for a camping/fishing trip in the MN Driftless area. It was a very close-run thing whether I went fishing, or just kept driving that fun car on those fun roads.. not what I’d expected at all.

Ryan Dutra
Ryan Dutra
2 years ago

Check out the Porcupine Mountains sometime. The roads in in very rough shape, but the area is quite beatiful with lots of twisty roads. Would be perfect if you had some sort of bastard half-breed of a GT car with WRC underpinnings.

Philip Ogston
Philip Ogston
2 years ago

Everybody check out Roadcurvature.com. The hero who made that site developed an algorithm based on open maps which rates roads on how twisty they are, and maps them out. Its a great tool for exploring interesting drives and rides. You do have to use some sense, the map tool doesn’t always know a scenic highway from a farm road up a ravine. But it is a cool way to find hidden gems.

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