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.

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. โ€“ 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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43 Responses

  1. 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.

  2. Wow! Mercedes is here too! This is awesome. I just want to give you a shout out… You were they only writer at “that other website” that moved me out of the greys after 3 years of dutiful commenting. So happy to be reading your articles again!

  3. When I lived in St Paul and my dad lived in Peoria, I would always take the US 52 route down the Minnesota/Iowa side instead of the Interstate. Cuts through the corner of the Driftless area. It added two full hours to the trip, but I wasn’t in a hurry, and found out that I got there in a lot better mood.

    Go further north and a little west, and there are some incredible roads in Minnesota and NW Wisconsin. Not anything you want to be tearing ass around, but nice twisty turns and beautiful scenery. Even the highways. US 2 and US 61 are both well worth traveling, with state and county roads offshooting into the woods if you want to explore more. Those roads are how I put 60,000 miles on a VW Golf in two years during college.

    1. I haven’t done it in over a decade so things may have changed, but the drive from Duluth MN to Ely MN is both incredibly scenic and fantastically fun–curvy, hilly forest roads with minimal traffic and maximal speed limit (I think it was like 70 last time I did it? Honestly I had all the fun and didn’t ever reach the speed limit)

      1. MN state highway 1? Yep, that’s a good one. Wisconsin Hwy 13 from Superior to Ashland is another good one. And if you keep going east, you hit the UP of Michigan (ya hey), and that’s nothing but good scenery and twisty roads.

  4. I have never driven in the Midwest, but it sounds beautiful.

    You should do a feature where we have readers chime in with one road or route from their state. It would be interesting to see what we all enjoy.

  5. Wow. Holy Crap! This is the first time anybody has ever called out my old home town.

    My parents bought a lot on Blue Spring Lake in 1954. Dad built the house with his firehouse buddies and that’s where we spent summers till full timing it in 1968.
    Among other High Schools (moving for Dad’s Jobs) I finished the last two years at Palmyra High back before they worked to make it touristy and it was a full on Farm Town with a Gamble’s store and everything. Worked at a service station there where I learned a lot about wrenching and of course sex ’cause the Gas Station is where that happened back then.
    So yes – beautiful riding and driving in and around the Kettle Moraine!

  6. I’ve been to the US Grant home in Galena before. Been a long time since I’ve been out that way.

    I’m currently in NE Indiana where we face a similar problem with most of the “scenic routes” that follow straight stretches of road dotted by cornfields and the occasional super-faded and tattered”F*ck Biden” flag (not bringing politics in here – just being truthful about what this area is like). However, there are some gems worth driving to see here – Cedar Creek Canyon is notable for some hilly tree-canopied roads with beautiful color changes seen during the autumn months. The roads near the Salamonie Reservoir are equally impressive, and then finally cap off your trip with a visit to the ACD (Auburn-Cord-Deusenberg) Museum in Auburn, Indiana. The view of a straight-8 in a Deusey model A or model J is quite a sight to behold when walking the exhibits there.

  7. It’s weird reading an article about the area I grew up in. The Kettle Moraine is about as good as you can get in the SE corner of Wisconsin, but it’s not a very large area. I’ve ridden about every road in the Southern Kettle Moraine area having grown up there.

  8. 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.

  9. 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.

  10. Everybody check out 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.

  11. As someone who grew up near Bagley (it was the weekend party spot when I was in high school), I still went “WTF is Glen Haven”. Tiny indeed. ๐Ÿ˜€

    I mentioned this on the other site when you had an article about good driving roads in the area, but anywhere on the Wisconsin side of the Mississippi from Winona to Wabasha (at least) is a great place to just get lost for a few hours. I will occasionally drive over there and every time I come to an intersection I check the map and go the direction that looks most curvy. I’ve rarely been let down by that strategy and have found some great roads in the process.

  12. Wisconsin here. My ND Miata and I drive with a sports car club (not Miata specific) mostly on the narrow, twisted roads in Iowa county and western Dane county. Beautiful scenic roads and challenging at the same time, many cut along narrow, meandering valleys. And if you’re headed to Road America in Elkhart Lake from the south, pick up State Highway 67 at the Illinois state line. It’ll add at least an hour to the trip but you won’t be sorry.

  13. Awesome read, Mercedes. The driftless area is a gem.

    One other Wisconsin curvy road I recommend (that is filled with water) is the Namekagon river between Lake Namekagon and Grantsburg where it meets the St.Croix.

    That section is approximately 149 miles via canoe (if I’m remembering correctly). It’s absolutely spectacular and virtually people free. Campsites can be found all along the way. There are numerous outfitters that can give you shorter routes for smaller sections if your ambition is less than a four or five day trip for the whole thing.

    (The first section between Lake Namekagon and Cable is sketchy as hell so maybe start at Cable if you don’t enjoy walking your canoe over beaver dams.)

    Plus, you can swim almost anywhere among the way. Just pull up to a sandbar and have at it.

    Note: Some paddling skill is required for any river journey and the Namekagon is no exception. Take someone who has some experience as there are some rapids here and there you need to navigate properly to avoid swamping your canoe. Also, good dry bags are a must.

  14. I live in Southern Wisconsin and can confirm that there are some awesome twisties throughout what the glaciers left behind. Should you get bored with that then the scenic drives through the Driftless Area, especially around The Dells, will certainly take your breath away as will the cliffs along the Mississippi.

    Car or bike, the upper midwest is a great place for summer exploring ๐Ÿ™‚

  15. The bluff campsites in Wyalusing overlooking the Mississippi are pretty spectacular too. Don’t forget to stop in New Glarus for a beer and a liverwurst sandwich while you’re in the area. If you’re going as far as Minnesota then you really should take highway 16 to Lanesboro. Riders need to look out for gravel on the corners and Amish buggies. I crested a hill one time and came across a couple of burly guys with beards wrestling with a spooked horse. Not your typical road hazard.

    1. If you’re in New Glarus then also head toward Spring Green along county HH. It’s not very long, but twisty. You’ll get to it off 51 between Blue Mounds and Dodgeville. While in Spring Green, House on the Rock and Frank Lloyd Wright’s old school are worthy places to go past or to. And from Spring Green head toward Devil’s Lake. Do this in October for maximum colors.

    2. Shh, it’s already impossible to get reservations for those campsites. ๐Ÿ˜›

      Also, basically all of the roads around Lanesboro are fantastic drives. It’s one of my goto destinations when I’m looking to turn some dead dinos into fun. 250 is actually my favorite road there – even the bit that looks straight on the map is a rollercoaster-like ride because of some pretty significant elevation changes. I usually drive that and 30 (which has some fun sections too, including back-to-back 90 degree corners) to Chatfield. I’ll also take 16 from Lanesboro to Rushford, then leave Rushford on 30, turn on 25 to Peterson, and then 16 back to Lanesboro. That’s a really fun and scenic loop.

      Oh, and my new favorite section of road is 76 between Houston and Caledonia. It’s about two straight miles of linked turns and the only drawback I’ve found is that traffic has been kind of heavy every time I’ve been there. It was not fun coming around a sharp corner and seeing a 40 foot fifth wheel halfway into my lane.

  16. The roads were a major disappointment when I moved to the Detroit Metro area after growing up in the South and living in California and WA. One of the reasons I bought my current house is because the road leading to it (Orion – about 10 miles north of DT) has sequence that reminds me of Eau Rouge!

  17. This was great. Now I propose we get JT and DT to send you on scenic roadtrips. I nominate a trip through the White Mountains, across the Kancamagus Highway, and through one of the Notches near Mt. Washington (maybe with a detour up the Autoroad). Mercedes does America!

  18. Oh, I bet Jason and David are soooooo glad the comments don’t allow for pics or gifs right now.

    So instead, just image the image of Beavis and Butthead giggling their asses off right now.

    Also, I’ve heard the Pan-European Natural Intercontinental Speedway makes for a great week-long ride. Never tried it myself, but I have to confess, I’m curious.

    1. That’s a long, hard ride. You’ll need some training first. Since you’ll be near the start/tip of the P.E.N.I.S., in Malmo, Sweden, you can shoot right over to Koenigsegg and take a couple of training courses. That way you’ll be better prepared not to blow your load prematurely, so to speak.

      I’d recommend starting with “Creative Operation of Cars, by Koenigsegg (of Sweden),” and then you’ll be ready for “Driving, Intermediate Course by Koenigsegg (of Sweden).”

      I’ll see myself out…

  19. Great article! This is such a nice area to drive. I’m more familiar with roads further North along the Mississippi, as that’s where my grandparents used to live. They had a three-story limestone house that overlooked the river and railroad tracks. I can say from experience it’s equally fun zipping along through the curves in a ’91 Celica or lumbering by like one of the river barges in a ’67 Cadillac.

    Also, the TWAT sounds fun – something to really get into. I’ll talk to my wife about it, but she’s pretty adventurous so I’m guessing she’ll want to come as well.

  20. Don’t know if my travels will ever take me out that way, but any similarity to the Tail of the Dragon is promising.
    Took that once in the Prius, as fast as I dared, and it was one helluva fun experience! I’m sure the photogs at some of the S-bends had a giggle but nobody on my tail complaining! Then caught up to someone with less desire to push those corners and had to take it easy.

  21. As a resident of Wisconsin’s Driftless area I can attest to the beautiful (though sometimes poorly maintained) roads. Having said that, please slow down and enjoy the scenery. If you want to drive fast and drift around corners, THIS IS NOT THE PLACE! We have a large Amish community that also uses these roads along with many bicyclists that also enjoy these roads. And don’t forget to watch out for the farmers!

    Stick to the Interstate if you’re in a hurry. Please.

    1. Very good note! I obeyed the speed limits when I was out there. That dirt road between Bagley and Glen Haven had residents and kids just casually enjoying the scenery for themselves. Yet, someone in a Civic blew by myself and the residents going what had to be 70 if not more. That road has a speed of 25 mph, so it was particularly bad.

    2. Yeah, I’m also from this area — besides the Amish and the [bi] cyclists, there are tons of deer and turkeys that will ruin your day or worse, so care is warranted when enjoying these great roads.

      I live on a twisty county “letter” road, and have witnessed a motorcycle + deer fatality at the end of my driveway — yearling jumped out of the corn in front of the cycle, rider and fawn both died.
      And turkeys — don’t laugh — a turkey thru the windshield isn’t fun. The windshield guys out here told me it’s their #1 call. I have nearly hit / been hit by a turkey too many times to count.

      1. I hit a turkey going 70mph recently, it just walked right out in front of me from behind a guardrail. I’m still picking feathers out that were embedded in my grill. Didn’t mean to hit it, but they have no sense of danger of what a speeding car represents. Glad I wasn’t on a bike

      2. When I was in eighth grade, we went on a field trip down to see the Illinois state capital. On the way back, the bus hit a pheasant and it went through the windshield. We were all OK, the pheasant obviously wasn’t, and the mess was considerable. As was the screaming from many students in the first couple rows as blood and feathers rained down.

        Fortunately we were only half a mile from a place I’m sure Mercedes is familiar with: Dixie Trucker’s Home, on I-55. Forty eighth-graders milled around the truck stop, eating diner food (the teacher paid for everyone’s dinner, which was above and beyond, thinking back) and playing arcade games for four hours while we waited for a new bus to show up.

        I don’t remember a thing about the field trip itself, but man, do I remember the day. I learned to watch for wildlife, and a newfound respect for safety glass.

    3. Agreed, most of the time we are there with the expedition mobile and all I can think of is how much of a riot it would be with the Del Sol. Viroqua is absolutely our favorite place in all of Wisconsin, and we live near the river and the lake near Milwaukee. The food, the people, the art, the roads. the camping it all is just stellar. And in a typical Wisconsin cliche, it hasn’t been flat landed like Door County. Sorry Mercedes, but it is pretty mcc true. Also, Highway 2 from Beloit area to Moline along the Rock River is an amazing road. Glad you are here and please keep being just who you are.

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