Take me home, country roads to where Midwest driving magic unfolds
Published on Jun 25, 2025 at 11:14 PM (UTC+4)
by Molly Davidson
Last updated on Jun 25, 2025 at 10:56 AM (UTC+4)
Edited by
Kate Bain
Move aside Pacific Coast Highway and Route 66, the best driving road in the Midwest isn’t where you think it is.
Forget what you’ve heard about Midwest roads: the flat, the straight, the kind that fade from memory.
Just a few hours out of Chicago or Milwaukee lies something different entirely – a region that feels less like Illinois and more like a back road into West Virginia.
Out here, the roads aren’t just scenic, they feel like a homecoming.
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This isn’t West Virginia, but it might just feel like it
The Driftless Area is what the Midwest looks like when glaciers leave it alone – a landscape of surprise curves, steep climbs, and limestone ridgelines.
Start your drive west from Chicago on Route 20, and the land slowly transforms. By Galena, the roads begin to breathe.
Galena is quaint and pretty, but keep going. Once you pass Dubuque and cross into Wisconsin, it all opens up.
No single route defines the experience. The best plan is no plan – just follow the Mississippi and trust the road.
And the magic? It’s in the quiet. No traffic, no billboards – just the sound of your tires and the open sky above.
Midwest country roads that take you somewhere you didn’t expect
The deeper you go, the more it gives – springs, caves, eagle sightings, and empty backroads lined with wildflowers.
Whatever your ride – roof down, visor up, or windows wide – the roads here make everything feel like the right choice.
It’s family-friendly, too. Campgrounds, fishing holes, and small towns like Glen Haven and Wyalusing make perfect pitstops.
This is not a place you rush. The Driftless rewards you for slowing down, turning off your phone, and just… listening.
It might not be the Blue Ridge Mountains, but it’s got the same soul – and out here, that’s enough.
Most people don’t come to the Midwest for the drive, and that’s exactly why it’s worth doing.
Because sometimes, the most beautiful roads aren’t the famous ones. They’re the quiet ones, tucked into river valleys and limestone hills, waiting to be found.
And while it’s not West Virginia, these country roads might just take you home all the same.
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Molly Davidson is a Junior Content Writer at Supercar Blondie. Based in Melbourne, she holds a double Bachelor’s degree in Arts/Law from Swinburne University and a Master’s of Writing and Publishing from RMIT. Molly has contributed to a range of magazines and journals, developing a strong interest in lifestyle and car news content. When she’s not writing, she’s spending quality time with her rescue English staffy, Boof.
