A Family-Friendly Road Trip Across Wisconsin
A three-day road trip itinerary for families to feel out the very best of this state
“What are your vibes?” a girl asks me at Genna’s Lounge in Madison, Wisconsin. It is nearing midnight under the hazed glow of the Capitol Building on a Friday, in an emphatically college-y scene in this emphatically college-y town. How to answer? Maybe I’m confused by how young people talk. Maybe I’m a bit thrown by the fact that in the last few hours I’ve been on a literal hamster wheel at a kids’ museum and pondered sirloin with onion rings at a late-night steakhouse. Or that earlier today, my family and I strolled the remnants of a 1,000-year-old civilization and that tomorrow we’ll be crossing land so singular it is described by what was done to it by glaciers: Driftless. Maybe I’ve just had one too many Moon Mans.
When a brutal Wisconsin winter finally—finally!—cedes, a newfound light is palpable, and it stretches like an open road, beckoning you toward a teensy towns and log cabins and Culvers-for-in-the-car, lakes and rivers and hotel pools, maybe a kayak, maybe skipping right past the tourist-saturated Wisconsin Dells toward Northwoods bonfires and roadside cheese stands, bait shops for emergency bathroom stops, and a siren song of bars and breweries. The quotidian pleasures of movement, of living, of leaving snow behind when possible and going, as the state motto says, forward, are obvious. But, what are the vibes?
Here, then, is a three-day road trip itinerary for families to feel out the very best of this state.
Who am I: A longtime Milwaukee resident, writer, and Kerouac-aping dreamer whose normal wander lusting usually leans south and metro-y. But it might be time for a reset, a scene shift toward the north, the west, and the window-down walkabout spirit of winding and weaving and doubling back and easing up on the gas to let the local state air sink in, and sit, once and for all.
The car soundtrack:
The latest from Justin Vernon, aka Bon Iver, hometown hero of Eau Claire, is about embracing joy, moving home and falling in love all over again with the Badger state. Meanwhile, the final leg here will take us to the home state of Bob Dylan, near the start of Highway 61, so—Highway 61 Revisited. For the inevitable road trip lulls, there is the undeniable funk of Minnesota’s favorite son: Prince.
What to pack:
A flannel or hoodie—those sun-up temps are cruel tricksters, and the roadside firewood stops are not mere suggestions: If you are doing it right, you will be drinking a beer in front of a midnight crackle and hiss before long. Also, if possible, bring a non-vegetarian and non-vegan appetite. This is a wonderland of beer and sausage and cheese.
Day 1: Milwaukee to Madison
Distance: 80 miles
Start driving: Pointing the car out of the southeastern corner of the state can sometimes feel like an exercise in diminishing returns. Milwaukee is but a medium-sized city with medium-sized expectations, yet here we have multitudinous foods, we have diversity, we have, for now, Giannis. And yet, right over there, an easy hour away, is the collegiate town of Madison, Milwaukee’s little sibling, all cleaned up and put together.
Stretch your legs: It feels almost disrespectful to bullet-point Aztalan State Park, the spot of a thriving Mississippian people that flourished in the area in the 10th to 13th centuries. Almost exactly halfway between Milwaukee and Madison, it is a spiritual destination in and of itself, offering a sweeping quietude that stretches among the widespread earthwork ceremonial mounds and wooden stockades. Although it is a perfect pit stop to let kids wander and wail and hill climb and trace the Crawfish River until their little legs are grateful to get back in the car.
Worth the detour: The town of New Glarus, 30 minutes southwest of Madison, is the venerable postcard of polka-y middle America quaintness, and its eponymousbreweryis the first woman-founded brewery in America.
You've arrived:
- Once you pull into the downtown isthmus, work your way through the coffee shops and tattoo parlors to end up in a sleek plasticky strip mall, featuring Casetta Kitchen and Counter, with a menu of fancy Italian meat sandwiches and a line out the door, around the corner, seemingly extending back to where you can’t see over the horizon. They must be great. Or, instead of waiting, you might head around the corner to Paul’s Pel’meni, a counter service late-night nook offering one thing: diminutive Russian dumplings. Beef or potato, chile-sauced and cilantro-ed, they’re served with infinite love and zero ceremony in a car-ready to-go box. Or hunker down in the back bar.
- Around a curving bend is the Madison Children’s Museum, a homegrown collective built on the backs and minds of some 600 local contractors, artists, and businesses. Inside, you’ll find a kid-friendly pop of colors and angles, hanging cow statues and cheese, wall doodles, and a Mr. Rogers feel. Oh, and a human hamster wheel. Situated across the street, Bradbury’s Coffee is more than just convenient caffeine; it’s a packed sliver of a space where 20-somethings play complicated card games over flat whites and savory buckwheat crepes. The coffee is strong and serious, making the combined blocks seem a microcosm of the city itself—small, concentrated, thoughtful.
- This spirit can easily extend to dinner—beers or Old Fashioneds and the homemade Crunch Wrap Supreme at the Young Blood Brewing Company. Or maybe try the Settle Down Tavern, a low-lit, buzzy scene of bric-a-brac and cocktails, crispy-edged smash burgers, and crackly fried cheese curds to tip kids toward sated sleep. If adult hangout time is possible, you can’t beat those of the Tornado Steak House, an exemplary Rat Pack lounge meetup spot that’s classily laid back and tracked by the Meters and the Delfonics and Tiffany-style lamp lighting. Order from the late-night menu that includes New York strip, French onion soup, escargots, or, yes, of course, cheese curds.
Stay the Night
Day 2: Madison to Viroqua
Distance: 95 miles
Start driving: Some 115,000 to 12,000 years ago, retreating glaciers deposited sediment known as drift throughout much of the world, especially what is now North America. Not here. This pocket of Wisconsin, Minnesota, Iowa, and Illinois was never covered in ice, resulting in a sharper, steeper topography of rolling, meandering hills, ridges, and coulees, carved by curving, tree-lined roads. The between-glacier space has also left a proud and distinct approach to rural living, and become a popular destination for a little away-from-it-all psychic liberation. Or, as they might say back in Madison, it is a vibe.
Gas up and fill up in Madison at Wonderstate Coffee or the Dane County Farmer’s Market, a year-round, Wednesday and Saturday Capitol Square smorgasbord of food, arts and crafts, and street music. Either will serve well for the road ahead that weaves through farmland densely populated by cows and horses of varying colorways and enough galloping deer at sunset to warrant a slackening of the pace. For us, it will eventually end at Viroqua, a place that reads like an idyllic montage of smalltown, front-porch idealism.
Stretch your legs: An hour or so outside of Viroqua, there’s House on the Rock. It is difficult to describe Alex Jordan, the inventor, architect, enigma, who fused Howard Hughes’s eccentricity, Frank Lloyd Wright’s imitation, mad scientist innovation, and hoarder accoutrement into, well, a house, built onto a rock. Part weirdo museum and part surreal fever dream, the attraction is not for the claustrophobic or acrophobic. There’s an infinity room, a Japanese garden, an impossibly sized whale sculpture, and an overriding feel of Seussian wonder and hodgepodge.
Worth the detour: Frank Lloyd Wright’s Taliesin, in nearby Spring Green, is a prime example of the Prairie School, and a savage glimpse into the local architect’s personal history and professional ambition.
You've arrived:
- For all its self-advertised “slow life,” the town of four thousand boasts not a small amount of things to explore. You can spend a full rudderless day wandering between coffee and bagels at Wonderstate, and strolling the postcard Main Street of gelato, vintage clothes, records, and a public market. Amble over toward Driftless Books and Music, a picturesque outpost reminiscent of all the images Instagram’s you’ve ever seen of Marfa, Texas. Inside is a sprawling and maze-like mashup of words and ideas in a pleasingly dusty collection.
- The main draw for many to Viroqua is the Driftless Cafe. Here, at this James Beard-nominated restaurant, the farm-to-table thing is manifested within the realm of the farming community. As in, the cows are just over there. The menu showcases many of the 200 organic farms in surrounding Vernon County. It also promises pizza with house sausage, charcuterie, an ever-changing menu that might have smoked trout cakes or local, of course, beef dumplings. The restaurant offers farm field trips, and the owner, Luke Zahm, is the host of the PBS show, Wisconsin Foodie. Yet it all remains somehow small town casual and easy—fussy fine dining with nary a brow raised at the presence of babies or toddlers.
- For a stomach gas-up on the way out of town, the beloved Viroqua Food Co-op offers a chicken, bacon, and garlic beauty of a car sandwich—it's hard not to take something, physical or otherwise, with you from such a bucolic bastion of art and possibility. Kids even get a free book for just walking into the bookstore.
Stay the night
Day 3: Viroqua to the Twin Cities
Distance: 183 miles
Start driving: The Great River Road is a National Scenic Byway that follows the Mississippi for 10 states, some 2,300 miles, and a multitude of streets and highways. Driving it, you’ll find yourself rolling alongside the vast, churning, almost lake-like river, going past inlets and hillside observation points, hatcheries and jutting rock formations, and over hulking ancient bridges. Coming through Lacrosse, you can cut across the state line to Minnesota, up through the rusty riverside burgs like Winona and Red Wing, the river narrowing and widening on a whim.
Stretch your legs: The National Eagle Center in Wabasha, Minnesota, is fit for stretching legs and wings. Or you can watch a bald eagle float with impenetrable grace and majesty, a symbol reminiscent of what our country once represented, maybe, right outside the window of your car, like a postcard, over the Mississippi River.
Worth the detour: An hour and a half outside the Twin Cities, bridge the young and the old of burgeoning Eau Claire, literally, by ducking in for icy beer-filled mugs, burgers, and waffle fries in a booth at Court n’ House, then cross the Chippewa River to Dotter’s Books, with its carefully-curated kids section. It's a friendly and meticulously maintained store indicative of the next wave of the place, at least in part inspired by Bon Iver’s Justin Vernon, who has moved back to his hometown, and was recently waxing poetic in interviews about playing basketball at his former school and discovering a new favorite place, Leona’s Pizza.
You've arrived:
- Once you make it to the Twin Cities, with kids tagging along, everyone seems to assume you’re headed for the Mall of America. But less obvious are the city’s other, less capitalism-focused attractions: Como Park, in St. Paul, has a free zoo and conservatory. The older, more chill of the Twins is also home to the Minnesota Children’s Museum, the Minnesota Museum of American Art, and the Bell Museum and Planetarium. Then there is the Science Museum of Minnesota, where river views are the backdrop for displays both sprawling and smart, expected (pull up a heavy fish!) and not—like long-ago scientific quakery, or a crushingly yet crucially frank all-ages presentation on stolen Native lands.
- Scant minutes up the road is the historic Waldmann Brewery. The Civil War-era structure is the oldest saloon building in the Twin Cities, with homemade German pilsner and ancient pine floors. It’s a good place to remind kids how people used to sit, simply, in end-of-day calm, enjoying each other’s company. And drinking. Down the street, and 150 years back to the future, is Parlour, offering a buttery brisket and ribeye burger. Or there is Sweeney's, with pub grub, corner bar warmth, and a sprawling tap list, where you can unwind on the patio and maybe play the hook and ring game, just blocks from where F. Scott Fitzgerald rewrote This Side of Paradise.
- On the Minneapolis side of the river, things can get even more beery. Surly Brewing maintains its status as the big dog, but it’s just one in a hoppy sea of local beer-making. Bricksworth Beer Company serves an inspired, crackly-edged Detroit-style pizza; Pryes Brewing features featherball courts; La Dona Cerveceria offers a full menu of Mexican food plus a soccer field; while Sisyphus has pinball and shuffleboard. Also, seemingly all of them boast patios of endless elbow and running room—so, beery in a familial way.
- From here, a proper dad move would be to lead a tour just blocks over to the sprawling Bob Dylan mural, or, just a bit further, to the intersection of 9th and Hennepin, made infamous by the eponymous Tom Waits song, who pondered the nature of how a “clock ticks out like a dripping faucet, 'till you're full of rag water.” Maybe he took the River Road to town too.
- Of course, culinarily speaking, you're not really honoring cultural tradition without getting gooey with an oozing Juicy Lucy. Both Matt’s and 5-8 Club claim inventorship of the regional burger with the cheese housed inside the patty. Both will inspire fierce opinions. Listen to locals all you want, but maybe seek out your own nook. Perhaps it is The Nook—an old-school, greasy hang with a family-friendly bowling alley in the basement and a menu claiming to feature the favorite burger of locals’ most treasured hometown hero, former Twins catcher Joe Mauer.
- Local tip: For proper Juicy Lucy consumption: Take the temperature with the back of your hand, show a touch of restraint, but maybe challenge the server’s warning of abstaining “3–5 minutes.” For better or worse, we couldn’t fully wait, and new life seemed to gush in all directions in the form of molten American cheese rivulets. Laundry needs to be done after a road trip anyhow.
- Next, aid your digestion with a trek to St. Anthony Falls, the only natural waterfall on the Mississippi River, near the University of Minnesota campus and gently framed by the skyline. Or, you could venture a 15-minute drive out to the Minnehaha Falls—stark and serene, cascading over limestone, with sweeping trails and beavers buggering about. Vast green expanses might inspire exercise, endless stone step-climbing, and the classic parental game of pretending to throw kids over waterfalls. Fatigue warrants snacks, in which case, seek out Sea Salt’s seafood baskets and tacos. Or grab grub before leaving town at Afro Deli, a popular St. Paul counter-service stop offering Somali steak sandwiches and spicy beef sambusas with creole sauce—a savory memento for the trek back home.
