Road-Tripping Wisconsin’s Great River Road: A 3-Day Itinerary

Great River Road and Driftless Road Trip

Y ‘all know that I love me some Wisconsin. So, when an opportunity came up to road trip the state’s southwest corner by fork, I was all. in. Wisconsin’s Great River Road showcases the stunning vistas of the Mississippi River. The iconic scenic byway leads travelers straight into the heart of the Driftless Region, a unique area characterized by its rolling hills and valleys untouched by glacial activity.


Our Great River Road & Driftless Itinerary Overview

Wisconsin’s Great River Road and Driftless Region provide an unforgettable adventure, offering a seamless blend of natural beauty, cultural richness, and a serene escape from the bustling world. And did I mention we traveled by fork? That, too. Keep reading for an amazing road trip itinerary that celebrates food, drink, fun things to do, and landscapes all in one.

DAY #1:

  • Depart Eau Claire
  • Prescott
  • Stockholm
  • Pepin
  • Alma
  • Galesville
  • La Crosse

DAY #2:

  • Depart La Crosse
  • Cashton
  • Viroqua
  • Potosi
  • Platteville

DAY #3:

  • Depart Platteville
  • Blue Mounds
  • Mount Horeb
  • Madison

Depart from Eau Claire, The City of Bridges

Nestled up in northwest Wisconsin, Eau Claire is a vibrant and welcoming city situated at the confluence of the Eau Claire and Chippewa Rivers. Eau Claire, or “clear water,” is renowned for its thriving arts and music scene, with numerous galleries, live music venues, and local festivals that foster creativity and community engagement. Spend a couple days here and use it as your jump-off point.

Getting There & Around

  • By Air: I’m not gonna lie, Eau Claire is a little ways out there. But it does have its own airport—the Chippewa Valley Regional Airport (EAU).
  • By Bus: If you’re not particularly interested in a connection (as I wasn’t), I suggest flying into Minneapolis (MSP) and bussing out to Eau Claire with Groome Transportation. Pick-ups stop at both Minneapolis Airport terminals, shuttles depart every hour, and it’s less than a two-hour drive.
  • By Taxi or Rideshare: Should you fly directly into Eau Claire or take the bus, you’ll quickly find that Ubers are not particularly plentiful. Be patient, and if all else fails, call a cab like in the olden days. (Groome has taxi contacts inside if your cell signal is nowhere to be found.)
  • By Rental Car: Probably your easiest route. Especially since, you know, you’re going on a road trip and all. Be sure to check parking costs (if any) at all your hotels along the way.

Where To Stay In Eau Claire

Highly, highly recommend The Oxbow Hotel. Central location, cute and comfortable rooms, restaurant and bar on site. Plus, every room has a record player and you can borrow three vinyls per room from the owner’s personal collection. Yep, this is small town Wisconsin. Ain’t it great?


Day #1 of Our Great River Road Itinerary: Eau Claire to La Crosse, WI

Yep, you’re gonna spend day one going full-tilt down Wisconsin’s Great River Road. Take in river views, lush landscapes, and—of course—stop for all the food and drinks along the way.

Must-Stops Along The Way

• Twisted Oak Coffee House in Prescott• Castlerock Museum in Alma
• Great River Road Visitor Center in Prescott• Buena Vista Park in Alma
• Stockholm Pie and General Store in Stockholm• Winghaven Pizza Farm in Galesville
• Villa Bellezza Winery in Pepin• Pack it in for the night in La Crosse

First stop? Prescott, Wisconsin. Where you’re gonna grab coffee and brekkie at Twisted Oak Coffee House. It’s the beginning of an epic road trip and you need to fill up. Twisted Oak served up an uber creamy white chocolate latte and an amazing ham and Swiss panini. Sit outside or upstairs, or take it to go. On your way to the Great River Road Visitor Center. Where you’ll lay eyes on thee Mississippi River you’ll be traveling down for the day.

On your way down, be sure to stop off in Stockholm, Wisconsin. Population 78. It’s a picturesque country town with loads of adorable shopping, great for a quick walk to stretch your legs. While you’re there, definitely stop at Stockholm Pie & General Store for a slice of their famous pie. The double lemon is award-winning, and confirmed delicious.

Keep heading south and you’ll find somewhat of a bizarre site in the middle of rural Wisconsin—an Italian winery, Villa Bellezza Winery. Absolutely worth a stop. Tour the cellars and vineyards, have a tasting, and grab a bite. This is the perfect place to enjoy the summer sun, drink in hand next to a fountain in the center courtyard.

If you thought an Italian winery was strange, you’re gonna love this next stop—the Castlerock Museum in Alma. As it would happen, an area judge spent a lifetime collecting historical arms and weapons. Eventually, the Castlerock Museum would come to be. Now, speaking honestly, I went into this stop kinda ho-hum, but left pretty dang impressed. Then, while still in Alma, drive up to the Buena Vista lookout for some jaw-dropping views. (Yes, it’s worth it.)

You’ll want to time your day for this last stop—Winghaven Pizza Farm in Galesville. Sunset. And happy hour. Enjoy pretzels, pizza, drinks, and live music out on a farm in the rural, rolling hills of the Great River Road region. It’s a truly epic way to finish off your first big road trip day.

And—don’t worry—your next stop is La Crosse. Where you can lay your head down to sleep for the night. You can get up and explore La Crosse in the morning, after a solid night’s rest.

Where To Stay In La Crosse

Home2 Suites by Hilton in La Crosse. Great location, clean rooms, comfy beds, even a kitchenette. Yes.


Day #2 of Our Great River Road Itinerary: La Crosse to Platteville, WI

I’m happy to report that today will be an easier—and shorter—day than yesterday. Spend some time strolling La Crosse in the morning before heading into Wisconsin’s incredible Driftless Region.

Must-Stops Along The Way

• Fayze’s Restaurant & Bakery in La Crosse• Potosi Brewing Company in… Potosi
• Amish country in Cashton!• Los Amigos Mexican Restaurant in Platteville
• Driftless Café in Viroqua• Also, sleep off those margs in Platteville

When traveling Wisconsin’s Great River Road and Driftless Region by fork, one must stop at Fayze’s in La Crosse and order the mimosa “flight.” Select four different mimosa flavors and what arrives will not be a flight at all, rather four whole mimosas. Which is such a great way to start the day, really. *Have a designated driver (duh).

Now, prepare yourself for Driftless’s Amish country. You’ll see bluffs and coulees galore, totally untouched by glacial activity, which in and of itself is striking enough. But you’ll also see real live Amish people. Buggies right next to cars, men working the fields by hand right next to tractors, and biker women buying pastries from barefoot, bonneted girls. Hit up Pasture Pride Cheese and Down a Country Road, if you can find them. And don’t trust your GPS.

After your brief time warp, spend a couple hours wandering Viroqua, another friendly small town nestled in the heart of Wisconsin’s Driftless Region. For lunch, I suggest Driftless Café, with their super fresh farm-to-table menu.

Surely, at this point, you’ve sobered up since breakfast and we simply can’t have that on Global Debauchery. Enter Potosi Brewing Company. Potosi, while super tiny, may have been one of my top fav towns on this Wisconsin road trip. Very old, kind of mountainous, and in the middle of it all… a brewery. With an awesome museum. Pay for second-level access and test out the Steamboat Shandy. Yum.

After two long days, you’ll be happy to learn that Platteville is your final destination for the day. Go for the 64 ounce Mermaid Margarita and beef chimichangas at Los Amigos Mexican Restaurant before checking in to your hotel for the night.

Where To Stay in Platteville

Don’t knock a shiny new Holiday Inn. This one in Platteville is money.


Day #3 of Our Great River Road Itinerary: Platteville to Madison, WI

It wouldn’t be a Wisconsin road trip without a stop in the capital city, right? So today, enjoy just a little more of the Driftless Region before heading back into the hustle and bustle of Madison. (And Madison is awesome, so I’m setting you up with a few more kick-ass things to do there.)

Must-Stops Along The Way

• Cave of the Mounds in Blue Mounds• Babcock Dairy Store, also in Madison
• Brix Cider in Mount Horeb• Genna’s Lounge in Madison
• Garver Feed Mill in Madison• Merchant for dinner… and sleep!

So, Potosi may have been one of my favorite top towns on the road trip, but Cave of the Mounds was definitely a top stop. Stroll the wildflower pollinators, mine for some gems, and—of course—head on down to explore the cave. Get the black lights for an extra special treat.

After a little communing with nature, head over to Mount Horeb… which is basically like troll capital of the world. It’s cute and kitschy (if you dig that kinda thing), but—above all—it’s home to Brix Cider. Super innovative cider flights and tasty grub (though service did take a little long).

Next, we’re keeping it moving by diving right into the big city. On your way in, hit up the Garver Feed Mill, one of those multi-use industrial spaces with pop-up restaurants and cafés and shops and art. Notably, though, they’re home to Nessalla Kombucha. If you’ve never seen a kombucha distillery, now’s your chance. It’s delicious and pretty cool, actually.

Nessalla Kombucha

We didn’t ultimately get to go, but I’m told an afternoon ice cream at Babcock Dairy should be on the list.

Followed by happy hour cocktails at Genna’s Lounge. Full disclosure that Genna’s seemed to be missing an ingredient from literally every cocktail I attempted to order (maybe the bartender was having a bad day), so I ended up with a basic cider. But I’m told the Old Fashioneds there are pretty epic. (Sadly, I don’t care for bitters.) The location and outdoor atmosphere, however, can’t be beat. Full view of the Wisconsin state Capitol.

This would be contrasted by the service at Merchant, where they went out of their way to make me my all-time favorite cocktail… the Pornstar Martini. The atmosphere was gorgeous and the food was tasty. Couldn’t have been a better way to end our road trip.

Where To Stay in Madison

For the best view in town, stay at none other than the Best Western Premier Park Hotel. Directly across the street from the Capitol building and only a block or two from one of Madison’s lakefronts. The beds are next level and there’s a rooftop bar to boot.


The Ultimate Great River Road & Driftless Region Itinerary

Unfortunately, all good things must come to and end, right? Wisconsin’s Great River Road and Driftless Region offer front-row seats to the mesmerizing vistas of the Mississippi River and a unique geologic area. This road trip itinerary 1000% provides an escape from the ordinary. And thank you, Wisconsin, for showing me amazing time yet again.

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Cheers, Jordan