What are good places in the midwest to vacation? Here are some top picks for your next trip!

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Alright, so folks sometimes give me that look, you know? When I mention taking a real vacation, not just a weekend trip, somewhere in the Midwest. They’re thinkin’, what’s there? Cornfields? Maybe a big ball of twine? And yeah, I get it, I used to be a bit like that myself. Always dreaming of coasts or mountains way out west, or some fancy international spot.

What are good places in the midwest to vacation? Here are some top picks for your next trip!

But then, a few years back, my big, meticulously planned overseas trip completely blew up in my face. Don’t even ask. Involved a very expired passport, a non-refundable ticket, and a whole lot of me kicking myself. Suddenly, I had two weeks of vacation time, a serious case of the blues, and absolutely nowhere to go that wouldn’t cost another fortune I didn’t have after that first mess-up.

So, I started looking. More like, I was forced to look. Grumbling the whole time, mind you. My wife, she’s a trooper, started pulling up these articles about places I’d barely heard of, or if I had, I’d dismissed them. “What about the Great Lakes?” she said. “Or those little towns in Wisconsin?” I was skeptical, man, truly skeptical. Figured I’d just end up bored in a different setting.

My Forced March to Midwest Appreciation

We ended up picking a spot in Michigan, mostly because it was drivable and we found a decent cabin rental. Figured, worst case, I could just read a book by a lake. And you know what? It started to click. We went to Sleeping Bear Dunes National Lakeshore. I wasn’t expecting much. Dunes? In Michigan? But climbing those things, seeing that massive freshwater lake stretch out like an ocean – it was something else. Totally different from what I had in my head.

Then we spent a few days just poking around small towns. Found this amazing little bakery, went to a local fish fry. It wasn’t flashy, not like the big city trips I was used to, but it was… nice. Relaxing. Real.

That first trip, born out of pure travel disaster, kinda opened my eyes. It made me think, “Huh, maybe there’s more to this middle part of the country than I gave it credit for.” So, the next year, instead of automatically looking for flights to somewhere far-flung, we decided to try another Midwest spot. This time, with a little more enthusiasm.

What are good places in the midwest to vacation? Here are some top picks for your next trip!

What I Actually Found Out There

Over the next few years, we actually made it a point to explore. And it’s not just one kind of thing. It’s a whole mix, really.

  • Door County, Wisconsin: We went there for the fall colors. And the cherries, man, the cherry pie. It’s got this whole peninsula vibe, cute towns, lighthouses. We rented bikes, went hiking. It was surprisingly scenic.
  • The Black Hills & Badlands, South Dakota: Okay, this one blew me away. Totally different landscape. We did Mount Rushmore, sure, but Custer State Park and the Badlands National Park were the real stars. Felt like another planet sometimes. We even saw bison just roaming around.
  • Mackinac Island, Michigan: This was a trip back in time. No cars allowed. Just horses, bikes, and fudge. Lots of fudge. It’s kinda touristy, yeah, but charming in its own way. Staying overnight after the day-trippers left was key.
  • Hocking Hills, Ohio: We wanted some good hiking, and this place delivered. Waterfalls, caves, forests. It’s not the Rockies, but it’s beautiful and rugged in its own right. We rented a cabin with a hot tub, just chilled out after long hikes.
  • Chicago, Illinois (obviously): Can’t forget the big cities. Chicago’s got world-class museums, amazing food, that whole lakefront. It’s a proper city vacation, right there in the Midwest. We’ve done that a few times, always find something new.

So yeah, that’s how I stumbled into actually appreciating Midwest vacations. Started with a ruined trip and a bad attitude, and ended up finding a whole bunch of cool spots I would’ve just ignored before. It’s not always about the most exotic or farthest place. Sometimes, the good stuff is closer than you think, you just gotta be willing to look, or in my case, be kinda forced to look. Now, I’m the one telling people, “Hey, have you ever thought about…?” Funny how things work out.

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