Bet you didn’t know the Midwest had hills like this. | Unsplash/Ethan Walsweer
Bet you didn’t know the Midwest had hills like this. | Unsplash/Ethan Walsweer

Find a Taste of New England in the Driftless Area of Wisconsin

But with Mississippi River beaches, Frank Lloyd Wright buildings, and goat butter.

I’d wanted to visit the Driftless Area since I first heard of it about a year ago. COVID and its residual fallout limited my wife and I to road trip travel throughout most of the past two years, and that meant researching all the amazing places within driving distance of our Chicago home. We did the Upper Peninsula, dipped our toes into every Great Lake, spent weekends exploring Indianapolis, Louisville, and Nashville, and pitched a tent everywhere from Starved Rock to the Indiana Dunes.

But the Driftless? That remained uncharted territory—at least until we booked an Airbnb, loaded up the Jeep, and set our sights on western Wisconsin, the promise of rolling hills and farm-fresh cheese beckoning us all the way up I-90.

To put it simply, the Driftless Area is a topographical and ecological anomaly, stretching 24,000 square miles along the Mississippi River from southwestern Wisconsin and Minnesota down to northeastern Iowa and the northwest corner of Illinois. For reasons best left to the scientists to explain, the Ice Age spared this region from a prolonged frosty covering, in turn preventing widespread glacial deposits—or “drift”—from killing off the existing environmental features and leveling the earth.

Summer and Fall are Wisconsin trees’ time to shine. | Driftless Wisconsin

Dramatic bluffs, lush forests, and steep gorges with sweeping vistas abound in these parts, as do incredible views of the Mississippi and its many tributaries. Elevations can soar up to 1,720 feet at points, and thanks to its distinct natural makeup, local wildlife, agriculture, and land patterns mirror those found in New England—a sharp contrast from the flat prairieland that dominates so much of the Midwest.

Local geology made the Driftless rich in natural resources like lead and zinc. Thousands of miners, many of them immigrants, flocked to the region back when Wisconsin was merely a territory, making it the most populous area for miles. The tiny 19th century hamlet of Belmont in Lafayette County, home to the state’s First Capitol Historic Site, proudly showcases this history, as does the University of Wisconsin’s mascot—many of those early transplants lived fulltime inside their mines, earning them the nickname “badgers.”

Throughout the years, the land has given rise to other industries, from award-winning cheesemaking to world-renowned artistic endeavors. It’s here that you’ll find Uplands Cheese, the family-owned creamery behind the highly coveted Rush Creek Reserve (basically the Pappy Van Winkle of the cheese world). Iconoclastic architect Frank Lloyd Wright settled in the Driftless for decades, leaving behind a legacy that continues to shape the area via his 800-acre Taliesin Estate, proclaimed a World Heritage Site in 2019.

You’ll find plenty of Americana classics here. | Buffalo County, Wisconsin

But back to 2022. We picked out an Airbnb in Fountain City, a small town near the area’s far northwest edge just across the Mississippi from Winona, Minnesota. Home to a quaint Main Street, a few interesting bars, and a roadside curiosity called “Rock in the House,” Fountain City’s population taps out at around 810. The house we rented didn’t even have a street number—instead, the GPS led us down a dusty dirt road that dumped us right in front of the driveway. The dog, happily unleashed, started chasing rabbits into a wooded patch above the rental, and we got to work on our own Driftless itinerary.

From quirky attractions and pristine hikes to world-class dining and a whole lot of warm hospitality, Wisconsin’s Driftless Area is chock full of things to keep the average visitor good and busy. Here’s what you need to know.

Buckle up—curves are definitely ahead. | Wisconsin Great River Road

No matter where you’re driving in from, make it a priority to spend at least part of the journey along the Great River Road—AKA Wisconsin State Highway 35. The 250-mile-long route twists and turns its way through 33 deeply historic towns and gorgeous foliage, all the while hugging the Mississippi River. Between colossal bridges, postcard-perfect vistas, ancient rock formations, and striking cliffsides, it's no wonder it leads the charge as one of Wisconsin’s’ most popular scenic byways.

The Driftless Area’s cup runneth over with natural escapes. | Driftless Wisconsin

Get the lay of the land on a leisurely hike

If you’re looking for prime access to the Great Outdoors, you’ve arrived. The Driftless is littered with parks, preserves, refuges, and natural areas, most of them clustered along the banks of the Mississippi and Kickapoo River Valleys. Diverse habitats attract hordes of rare migratory birds and other unusual wildlife, while manmade features like hiking and biking paths, scenic lookouts, fishing piers, and rustic campgrounds draw in the humans.

Merrick State Park’s underbrush turns into little green islands when the river rises. | Photo by Meredith Heil

Up north, two state parks—Merrick and Perrot—are both excellent places to get your footing. At Merrick in Fountain City, you can follow three miles of well-trodden trails to catch a glimpse of the Mississippi-fed wetlands below, stopping to forage for mushrooms and other wild edibles as you go. Over at Perrot, 1,200 acres stretch out before you, broken up by soaring bluffs overlooking the confluence of the Trempealeau and Mississippi rivers. From there you can merge onto the Great River State Trail, a 24-mile expanse popular with cyclists looking to stretch their legs against a breathtaking backdrop.

Squad goals are real at Trempealeau National Wildlife Refuge. | Trempealeau National Wildlife Refuge

Elsewhere, a handful of State Natural Areas provide a slightly less rugged foray into nature. The 6,446-acre Trempealeau National Wildlife Refuge has long been a hub for massive Bald Eagles and other critters, while Buffalo County’s Whitman Bottoms Floodplain Forest State Natural Area buzzes with majestic herons, laying claim to one of the state’s largest rookeries.

The Kickapoo Valley Reserve, lodged between La Farge and Ontario, has multiple dedicated and mixed-use trails throughout its 8,569 acres, each with ample opportunities to observe cohabitating species. And just north of Prairie du Chien lies the Limery Ridge Savannah, one of the last undeveloped bluffs perched above the Mississippi River, and the ideal setting for spotting colorful songbirds flitting amid the open oak woodland.

Swimming in the Mississippi? Sure. | Prairie du Chien

Cool off in the mighty Mississippi

Raise your hand if you didn’t know the Mississippi River had beaches. Strange but true, a network of sandy shores welcomes swimmers, waders, and sunbathers every summer. Wyalusing Public Beach in Bagley holds it down as a family-friendly respite bordered by canoe trails. Over in La Crosse, Pettibone Beach is a sportier option, with impromptu games of catch and beach volleyball rounding out a disc golf area, fishing docks, and onsite kayak rentals. Go figure.

Kinstone Megalithic Garden, AKA Wisconsin’s Stonehenge. | Photo by Meredith Heil

Pull over for oddball roadside attractions

Bring on the kitsch—this is the Midwest, after all. Starting in Fountain City, blink and you’ll miss the entrance to Rock in the House, a local landmark whose small hand painted sign has beckoned drivers along North Shore Drive since the mid-1990s. Pull into the curving driveway, however, and you’ll encounter something you won’t soon forget: a 55-ton boulder bisecting the rear of the modest single-story house, shards of siding and plaster crumbling around its craggy mass.

It’s a rock. In a house. | Photo by Meredith Heil

The mighty stone rolled down the hill and smashed into what once was Maxine and Dwight Anderson’s primary bedroom in April 1995. No one was hurt, thank goodness, and the house was subsequently purchased by an area real estate investor who turned the site into a museum. The new owner kept everything perfectly intact, from the ruinous rock to the kitchen’s cheery wallpaper and outdated appliances, adding only displays showcasing relevant newspaper clippings and a few pieces of geological information. Sadly, the museum closed in 2021, but visitors can still walk around the exterior of the house and peer into its windows for a closer look.

Kinstone Megalithic Garden is yet another Fountain City original. The sprawling open-air exhibit has been likened to Wisconsin’s Stonehenge, a mystical collection of rock formations spread out over 30 rolling acres. For $10, passersby can wander the grounds for as long as they like, checking out the dramatic installations, meandering through labyrinths, and pointing out one of the garden’s many resident cats. They also hold regular events on the property, including art shows, concerts, celebrations, and yoga classes.

Prepare to be wowed. | Lamar Advertising of Central Wisconsin

A trip down to La Crosse brings you to the foot of the world’s largest six pack (no, you can’t drink it). City Brewery’s towering bright tanks stand 54 feet in the air, swathed in La Crosse Lager labels to make them resemble six enormous beer cans. Fun fact: They were originally the brainchild of G. Heileman Brewery, painted with Old Style Lager branding in 1969 as a successful marketing ploy. And if you do come away thirsty as all get-out, consider dropping by Bathtub Spring. The bubbling Star Valley beacon has been treating drivers to fresh, ice-cold spring water via a simple bare tap jutting out of a roadside creek for decades. Pull over when you see the porcelain bathtub (it acts as a collection reservoir) and help yourself to a drink courtesy of the tin cups chained to the pipe.

Dig into succulent prime rib at a classic Wisconsin supper club. | Digger's Sting Restaurant

Fuel up with some hearty home cooking

Beyond brandy-spiked Old Fashioneds and squeaky cheese curds, Wisconsin dining is synonymous with supper clubs, those lovable full-service restaurants that treat you like family whether it’s your very first fish fry or your 1,000th prime rib platter. The Driftless boasts its fair share of quality supper clubs, from the whimsical Golden Frog in Fountain City, established 1878, to classics like Westby’s Old Towne Inn Supper Club (order an Ice Cream Drink and thank us later), Sullivan's Supper Club in Trempealeau with its riverfront views, and Digger’s Sting, a La Crosse fixture oozing with retro authenticity.

The (self-proclaimed) oldest continually operating bar in Wisconsin. | Monarch Public House

If a steak dinner with all the fixings isn’t in the cards, a host of laid-back bars and brewpubs have your back. Highlights include Monarch Public House in Fountain City, a friendly Irish pub that dates all the way back to 1894 (we figured the dragon-centric decor was a recent addition). The self-proclaimed oldest continually operating tavern in Wisconsin, it’s decked out in historic artifacts from the hand-carved oak backbar to the pressed tin ceilings and everything in between. Grab a pint of their proprietary Fountain City Brewing Company Fountain Brew, post up on the patio beneath the shade of a monstrous dogwood tree, and don’t sleep on the Irish Nachos.

If you're in the mood for wood-fired artisan pies laced with locally sourced toppings, Suncrest Gardens Pizza Farm is another stellar option. Make sure to bring a picnic blanket so you can spread out and enjoy the bucolic surroundings while you feast.

Shhh—the Castlerock Sourdough loaves are sleeping. | Photo by Meredith Heil

Still hungry? Swing past Castlerock Sourdough’s Bread Hut in Fountain City. In late June 2020, accomplished sourdough master Britta McColl erected an orange storage unit at the edge of her driveway and began stocking it daily with her fresh-baked loaves. What started as a way to supplement income and use products during the pandemic turned into a hit. McColl, now back to her regular farmers market rounds, continues to fill the shelves with white, rye, cinnamon raisin, jalapeno cheddar, and more, all pulled right from the oven. Leave your payment in the lock box and help yourself.

Nordic Creamery pulls out all the stops. | Nordic Creamery

Stock up at a local creamery (or three)

What’s a trip to America’s Dairyland without stuffing yourself full of cheese? See if you can detect the Driftless’ particular terrior by sampling your way through award-winning small-batch cheeses, butters, ice cream, and other delicious dairy products. Family-owned and -operated since 1917, Nordic Creamery has picked up quite a few accolades over the years, hawking their wares from a gift shop just outside of Westby. Pick up a tub of goat butter—trust us on this one—and peruse the wide array of spreadable, hard, and soft cheeses on offer (the ice cream isn’t half bad, either).

Uplands Cheese Company’s flagship Pleasant Ridge Preserve. | Photo courtesy of Uplands Cheese Company

Elsewhere, Arena Cheese, birthplace of Wisconsin’s original Colby-Jack, is one of the oldest creameries in the state and definitely worth a visit if you find yourself in the Arena area. The same goes for Carr Valley Cheese in La Valle, a century-old cheese plant that strictly adheres to traditional processes.

And then there’s Uplands, the aforementioned Pappy Van Winkle of the curd-savvy, which perches atop Pleasant Ridge in Dodgeville. The farm (still family-run, of course) isn’t generally open for visitors, but you can pick up rounds of their nutty, Alpine-style Pleasant Ridge Reserve at nearby retailers like Spring Green General Store and Schurman's Cheese in Dodgeville. One tiny nibble of the delicacy,—produced during the summer months from grass-fed milk and encased in an all-natural, washed rind—and you’ll realize why it's literally America’s most-awarded cheese. Or bide your time until November, when they release their even-more-sought-after Rush Creek Reserve, a decadent, custard-like autumnal showstopper that sells out faster than you can say, “Pass the bread.”

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Meredith Heil is the Editorial Director of Travel at Thrillist. She lives in Chicago and enjoys all things cocktails, crosswords, and women's soccer. Send good vibes to @mereditto.