We use the word underrated a lot on this blog, but this part of the world is just that. I was reminded of that fact once again a couple of weeks ago as I partnered up with Travel Wisconsin on a road trip down the Wisconsin's Great River Road.

This stretch of Highway 35 winds along the Mighty Mississippi as it makes its way toward the Gulf. The region, also called the Driftless, is geographically and culturally unlike any other place in the country, with the river carving its way through rising bluffs that look like a miniature mountain range.

And I'm not just saying it's unique because it's beautiful — it really is one-of-a-kind. The distinct landscape comes from the last Ice Age, where glaciers drifted all over the Upper Midwest, leaving giant puddles/lakes behind as they flattened the land — but they forgot about this part. Hence, the name "Driftless."

The deep green valleys here are dotted with farms and sunflowers and wineries (wineries!). The small railway towns along the river each tell a different story. Some have been ghost-quiet for decades, while others have become thriving regional cultural centers for art, film and food.

For the Great River Road, underrated is an understatement.

To help you plan your own Great River Road trip, we've rounded up a few highlights from this epic adventure up and down the Mississippi. You can do this trip in any order that suits you — this order made the most sense for us from Minneapolis to La Crosse (and back again) over a long weekend.

Stop 1: Maiden Rock, Wisconsin

Our first stop was Maiden Rock, a little town of 121 people that sits right at the Rush River Delta. Legend has it that the daughter of Chief Red Wing of the Dakota Sioux, Winona, jumped off the bluffs to her death when forced to marry a man she didn't love. That's how Maiden Rock got its name, but its history since has been decidedly more positive.

Maiden Rock Cidery & Winery

Do you know this part of Wisconsin is wine country? And do you know that it's called the Great River Road Wine Trail? And do you know that we drank all the wine and there might not be any left for you now?

Just kidding, there's a little bit left.

Luckily, I wasn't driving so I tried pretty much everything they had in the cider, mead and wine departments (they even serve some New Glarus pours too). My favorite of the bunch was the flagship Scrumpy — a semi-dry, sparkling cider that's quite light and refreshing.

If you're with a group, they offer reasonably priced private tastings and classes — and the owners Herdie Baisden and Carol Wiersma really know their stuff. These two bought this farm with big plans but virtually no background in agriculture or vinification (Herdie is a retired organizational psychologist who started brewing as a hobby). Close to two decades later, they've studied and worked their behinds off to become regional experts on cider-making, wine-making and agricultural tourism.

Cultural Cloth

This store won me over in, well, no seconds. As we pulled up to the building in downtown Maiden Rock, I could already tell I was going to love instantly. The owners Mary Anne and Jody opened the shop in 2009 with a shared passion for textiles and supporting women artisans from all over the world. Every handmade piece is something special, from Guatemalan rugs to museum-quality Indian quilts. Luckily for me (but not for my bank account), they also have an online shop.

Smiling Pelican Bakeshop

The Smiling Pelican Bakeshop's pies and pastries came highly recommended, but alas, it was closed for the day by the time we arrived. Hopefully our baked goods-less Maiden Rock visit will help you avoid making the same horrible mistake and you'll get there in time.

Pick something up to tide you over until the next bakery stop (which is in 10 minutes).

Stop 2: Stockholm, Wisconsin

The town of Stockholm is quite special to me because my husband and I got engaged there at A to Z Pizza Farm. The town is a storybook sort of place, where I imagine an alternate version of myself living like a Gilmore Girl.

I'd be Lorelai, running the Stockholm Hotel or the Spring Street Inn and drinking too much coffee and eating too many cheeseburgers at Lena's Lucky Star and volunteering at the Flyway Film Festival.

Stockholm Pie Company & General Store

I've written about this bakery before. The blackberry-apple is amazing (it's got a hint of cardamom, which just makes the whole experience seem even more Swedish — the Dala horse in the window is kind of a giveaway too). Oh, and the caramel apple crunch pie is so good that I'm not allowed to buy a whole pie because I'd absolutely eat the entire thing alone. My suggestion? Call ahead and pre-order two mini pies and then attempt to share with at least one other human being.

The general store on the right side of the store is a nice place to pick up local queso, jams, wines, beers and the makings for a picnic.

Stop 3: Alma, Wisconsin

While Stockholm's roots are very Swedish, Alma's are Swiss. It's one of the larger small towns in the area and designated as a National Historic District, which translates to... extra cute.

We had to cruise through Alma quickly on Friday to get to dinner on time, and Sunday was a sleepy day without too many businesses open in the late afternoon. However, I'd love to return here to explore, stay at one of the B&Bs, drink a latte at a place called Coffee Wench and go to the only medieval armor museum I can think of.

Riecks Lake Park

You might blink and miss it, but this little roadside park in Alma has incredible views. The algae, while probably not the best sign for the lake, made the landscape look like Jurassic Park. This park is known for bird-watching as well — in October and November, huge flocks of migrating swans stop here on their way south. And birds are basically tiny dinosaurs, so it all makes sense in this setting.

Stop 4: Cochrane, Wisconsin

I don't know anything about the town of Cochrane, but I do know about their pizza farm.

Suncrest Gardens Farm

The Great River Road is rich with pizza farms — probably the most concentrated pizza farm habitat in the Midwest. So of course, we had to check a new farm out during this road trip.

We drove a few miles inland through the lush mini mountains into the peaceful Yaeger Valley just before sunset. We lost our cell phone signals. We started to wonder if we were going in the right direction. We thought about turning around and finding a good burger instead.

And then we saw a couple hundred cars, a plume of bonfire smoke, a live band and a bossy goat and knew we were in the right place.

It's hard for me to fully describe how magical this evening was. Despite the lengthy lines and waits for food (definitely come early!), it felt like we were at a backyard pizza party with a thousand friendly strangers and a few dozen happy farm animals.

Suncrest Gardens Farm (and its Thai Peanut Chicken Pizza) is a treasure to Wisconsin.

Stop 5: La Crosse, Wisconsin

We spent Saturday in the wonderful City of La Crosse, a college town where riverboats and polka reign. La Crosse is famous for their annual Oktoberfest celebrations, complete with beer, brats and accordions (as it should be), but there's so much more to this charming community than that.

The Charmant Hotel

This hotel is in a former candy factory and they give you chocolate at check-in.

(Okay, there's more if you're not sold already.)

From the duck confit hash and trout benedict brunch and the rooftop cocktail lounge to the lobby coffee bar and the super comfy beds, The Charmant is one of the coolest hotels in the Midwest. There, I said it.

It's owned by the same group that owns The Iron Horse in Milwaukee and the not-quite-open Hewing Hotel in Minneapolis, among a few others. They always do a great job of highlighting the history of the building and the culture of each city, so there are a lot of small, original touches like that throughout the property.

Cameron Park Farmers Market

When I'm in a new city, hitting up the local farmers market is one of my little rituals. It's a window into the heartbeat of the town, and this Saturday market was a blast. It's small, but you'll be able to buy strawberry bubble tea, great local produce from the local Hmong farmers and even breakfast ramen from Apothik Food Truck.

P.S. While you're there, make sure to check out the little fenced-in section of the park that's not public.

The Root Note

If I lived in La Crosse, I'd hang out here all the time. It's quite simply a hang out. They serve Kickapoo Coffee from nearby Viroqua, Wisconsin and have created a welcoming, progressive gathering place for artists, musicians, students and work-from-homers.

The Antique Center of La Crosse

When in La Crosse, you've gotta shop around. Most certainly at this antique mall, if nothing else. 74 booths and three floors of anything everything you could ever imagine. 1930s horse figurines? Check. Mid-century barware? Check. Huge 1890s U.S. Postal Service counter. Check. Creepy Treasure Trolls? Check.

Grandad Bluff Park

When I called on you guys to give recommendations for this trip, you all said we had to go up to this park. And you were all right, of course. You're smart people.

Standing on the the top of this wildflower-covered bluff is like being on top of the world. You can see the whole city and then another city and then another.

Turtle Stack Brewery

La Crosse has a long brewing history and there are several options for the beer-chasers among you. We stopped for a pint at Turtle Stack on the way to dinner (loved the Black Lager), but the Pearl St Brewery came highly recommended as well. Most of the local bars are very local beer-focused, so you're sure to find your old and new favorites all over town.

The Mint

Dinner in an adorable little house? Yes, I'll eat there.

The Mint is the hip, farm-to-table dining outpost near the university campus that serves lunch, dinner and brunch on weekends. We ordered a couple of drinks (don't skip the cocktail menu) and had a feast of Italian chard cannelloni stuffed with seasonal veggies, tender lamb and achiote grilled chicken with brown butter masa gnocchi.

Our biggest regret from this portion of the trip is that we didn't also come back for brunch in the morning.

The Pearl Ice Cream Parlor & Confectionary

There's always room for ice cream! Especially when it's from this cute 1930s-era soda fountain, candy shop and ice cream parlor that had lines out the door for most of the day.

Had we been up for more alcoholic nightcap (vs. the ice cream one), we would've checked out Bodega Brewpub or Digger's Sting, a dimly lit time-warp of a supper club and bar.

Riverside Park

This city park was right outside our hotel, so we spent a solid amount of time walking there in the morning and again in the evening, enjoying the perfect summer weather that weekend. (Also playing Pokemon Go, but that's neither here nor there.)

Saturday morning we just happened to be walking by when the American Queen riverboat pulled up and docked right there in front of us. And then we were walking around again at sunset and it just happened to be paddle-wheeling away, whistling a merry little organ tune.

It was so awesome.

The American Queen is the largest river steamboat in the whole world. It's "the riverboat Queen" that you imagine CCR and Tina Turner hitched rides on in the song where the big wheels kept on turning.

If he were around, Mark Twain would totally be chilling on this boat.

P.S. The other boats pictured are replicas of Christopher Columbus' Nina and Pinta (no Santa Maria though). They stop in about 40 cities per year, but this was their first time in La Crosse. They are about 800 times smaller than what I pictured during history class.

Stop 6: Trempeleau, Wisconsin

Trempeleau is French for "mountain whose foot is bathed in water."

That's not a joke. That's a real translation.

Perrot State Park

On Sunday, we got physical. Opposite the protected Trempealeau National Wildlife Refuge is Perrot State Park, where you can get a majestic view of the actual "mountain whose foot is bathed in water." I recommend packing a water bottle, putting on your real hiking shoes and climbing up to the top of Brady's Bluff from the west side. At the summit (when you've stopped panting), you can see for miles. You'll swear you're in Costa Rica and not Southwestern Wisconsin.

Trempeleau Hotel

After our Sunday morning hike, we had lunch at the Trempeleau Hotel. The restaurant is famous for its walnut burger, a perfect veggie burger without the veggies (I'm okay with that!). It's a delicious blend of walnuts, Wisconsin cheese, eggs, tamari, onions, herbs and bread crumbs. I remember saying, "I'm not that hungry." And subsequently eating the whole thing. The catfish sandwich is also worth a try, and staying for the live music in the garden outside is a must.

Elmaro Winery

Another score for Trempealeau — a phenomenal winery with stunning views.

My husband and I lived in California for a couple of years and I can tell you with confidence that this place really and truly feels like it's in Santa Barbara Wine Country. Like, our GPS said we were in Wisconsin... but no... couldn't be.

But it is!

Not only that, but the actual wine was incredible. Most Midwestern wineries can't possibly grow enough grapes to meet the demands of wine-making so they import them from other areas, but Elmaro sources many of their grapes from local vineyards. And though their sweet wines are most popular, I liked the dry white wines best. We took home a several bottles of the Vidal Blanc (light and citrusy), La Crescent (which won a gold medal at the Riverside International Wine Competition) and their sweet 100% apple wine too.

Stop 7: Nelson, Wisconsin

Nelson is home to the best cheese curds. And a field of sunflowers.

Nelson Cheese Factory

This ivy-covered, historic cheese factory doesn't actually make cheese anymore (spoiler alert: they stopped after over 100 years at the job). They do, however, sell a lot of fantastic cheese, both domestic and imported. And they make ice cream and sandwiches, so could you just forgive them already?

Nelson Cheese Factory is the kind of store you expect to find in a big city and crowded with hipsters. But it lives here where it has always lived, and that's even better.

When we arrived in Nelson, we were both still full from lunch, but we made room and snacked on squeaky cheese curds all the way home. There's always room for curds.

Thanks, Travel Wisconsin!

We honestly can't thank Travel Wisconsin enough for sponsoring this incredible trip, for giving us an encyclopedia of amazing ideas during the planning process and for supporting The Midwestival community (that's us! and you!). It was an absolute dream to partner with such a wonderful organization that shares our commitment to showing off the best of this region. We certainly couldn't fit everything into this one trip or this one post, so make sure to check out their many resources on traveling in Southwest Wisconsin. And check them out on Instagram @travelwisconsin, where you just might see a few of our photos in the coming weeks. :)

If you'd like to add something we missed on this trip, we'd love to hear from you in the comments!

Words and photos by Annie D'Souza

Show more