Cozy Cabins and Magical Shorelines Await in This Midwest State

And by Midwest we mean Mid-best.

Devils Island is one of Wisconsin's Apostle Islands. | Posnov/Moment/Getty Images
Devils Island is one of Wisconsin's Apostle Islands. | Posnov/Moment/Getty Images

As a child watching my friends go to Disneyland while I stayed behind in Wisconsin, I didn’t fully appreciate the Badger State. My family vacations consisted of local trips up north, getting as close to Canada as possible, usually in a rustic way that involved a campsite or cabin. To Milwaukeeans, “going up north” is kind of like “going upstate” in New York.

I’m no longer jealous of my childhood friends who waited in line to see adult-sized cartoon characters. Through our road trips, I got to see ocean-sized Great Lakes carving caves into cliffy shorelines, rolling hills once rounded by glaciers that allow you to see miles of flowery meadows, and woods surrounding so many lakes that spark a constant debate with a certain “land of 10,000 lakes” neighbor about which state has more. Between its 15,000 lakes, as well as Lake Superior, Lake Michigan, the Mississippi River hugging the western border, and okay, a lot of snow, all that water makes for more greenery than the surrounding midwest plains.

Yes, it can get cold here. But that means phenomenal fall foliage as far as the eye can see, as well as creative winter activities that stem from the saying about necessity being the mother of invention. Not only will you find snowshoeing and cross-country skiing in this mostly flat but gently rolling terrain, as well as ice skating on frozen ponds in the wilderness, you’ll even find ice cave treks and ice fishing in these crystallized lands.

Perhaps as another cold-weather consequence, the state is the proud home of PBR, Leinenkugels, Miller, Schlitz, and decades of strong craft breweries—plus all the bratwurst, pretzels, cheese curds, and other hearty foods to keep your belly warm. Essentially, Wisconsin is a place for cozy cabins in the woods, beer by the fire, a couple artsy cities keeping things current, and fantastic charcuterie boards—because cheese is what we do.

Spend a cozy afternoon walking around the Milwaukee Art Museum. | Photo by FRONT ROOM PHOTOGRAPHY


As the state’s largest city and unofficial culinary and cultural capital, you can’t visit Wisconsin and not spend a few days in Milwaukee. To the surprise of visitors who only associate the city with beer and cheese, Milwaukee has a thriving theater scene, a symphony orchestra, an opera, and the whimsical Milwaukee Art Museum (designed by famed architect, Santiago Calatrava, and deserving of attention both outside and inside). It’s also the birthplace of Harley Davidson motorcycles, as seen at the Harley Davidson Museum. Plus, the city is reviving its 20 year old America’s Black Holocaust Museum, which will re-open in early 2022.

For food, Alem Ethiopian restaurant has all the injera and spicy lentils you could want. Palomino bar has buffalo fried cauliflower, big comfy booths, and an ‘80s basement vibe in the best way possible. Crafty Cow is another solid brew pub famous for their hot fried chicken sandwich, which also has a vegan option. Or check out the Milwaukee Public Market, which has a range of choices from Mexican to Middle Eastern. The city is known for its over-the-top Bloody Marys (seriously, we put anything and everything into the brunch drink), so head to the St. Paul Fish Company for a fish fry and a boozy, bloody drink with a lobster claw poking out.

North Broadway is where you’ll find the most unique shops and galleries to peruse. Along the winding Riverwalk pedestrian path, you can snap a picture of the Bronze Fonz, a sculpture tribute to the Happy Days star that made Milwaukee famous in the 70s and 80s. Next, head south to Henry Maier Festival Park (known to locals as the Summerfest grounds), which host massive music, culture, and food festivals from spring through fall. In large part due to the Summerfest events (such as German Fest, Festa Italiana, Mexican Fiesta, Irish Fest, PrideFest, Black Arts Fest MKE, etc.), Milwaukee is also known as the City of Festivals.

If you don't move to Madison, I will. | Nejdet Duzen/Shutterstock


Madison is a city of university students, retired hippies, Frank Lloyd Wright buildings, and one of the highest restaurants per capita in the country. Madison is constantly ranked highest in the US for livable cities (first place in 2021, in fact), with its thriving arts scene, obscene amount of parks and bike routes, and local’s obsession with environmental sustainability. It’s also a city that forces us to learn the word isthmus, as it’s the only state capital to sit on a narrow stretch of land between two large lakes. In fact, there is no “north” or “south” Madison, since that sort of direction would lead you underwater—there is only East Madison, West Madison, Lake Mendota, and Lake Monona.

Take a walk down state street, with the lit up capital behind you, a shoreline ahead of you, and bars, shops, and music venues on either side. Stop for Laotian cuisine at Ahan, momos at Little Tibet, mediterranean pizza at A Pig in a Fur Coat, or bar hop the 10 block stretch of Willy Street on the hip east side. Nearby, Nook offers a tasting menu that turns familiar, childhood favorite foods like PB&J into elegant, deconstructed plates that befuddle yet comfort your palette. On the super casual end, both the Weary Traveler and the Old Fashioned provide the traditional Wisco experience of eating cheese curds with no-frills beer in a pub-like setting. Or watch the sunset dip behind the lake while eating brats (including vegan brats!) at Union Terrace, often accompanied by live bands.

For tranquility, roam through the Arboretum, with its miles of trails across wetlands, woodlands, and prairies. Or stop by the Olbrich Botanical Gardens, which has one of only four pavilions gifted by Thailand outside of Asia (and the only one in North America). Catch a performance at the Overture Center for Arts, see an exhibit at the brutalist Chazen Museum of Art, or hike along the ice age trail, lakeshore path, or Picnic Point, which has six sacred Native American effigy mounds. Take advantage of all those farms across the state at the biggest farmers market in the country, going strong since 1972 and sitting scenically in the shadow of the capitol building. Lastly, admire Madison’s official bird, which is a plastic pink flamingo, just to give you an idea of how seriously this city takes itself.

apostle islands
Yep, this is a real place. | Posnov/Moment/Getty Images

Apostle Islands National Lakeshore

National Parks get all the attention, but National Lakeshores are also federally-designated scenic areas, and northern Wisconsin happens to be home to one: the Apostle Islands National Lakeshore. One of the most stunning treks is the Meyers Beach Sea Cave Trail along the southern shore of Gitchigami, the name the Red Cliff band of the Lake Superior Chippewa gave the Great Lake. As the tribe’s name implies, this area (and this shoreline, in particular) is lined with red cliffs, which contrast against the bright green, densely-wooded forest surrounding the trail.

Hiking along the lake and above the sea caves is available year-round but, given the strong lake winds, kayaking is typically only available in summer. Come winter, those sea caves turn into ice caves, and if the lake’s water freezes to sufficient thickness, you can walk across it to get to the caves. Inside, you’ll find a fairytale-like backdrop of icicles in all shapes and sizes.

cranberry bog harvest
If you ever wondered what a cranberry big harvest looks like, well, now you know. | YinYang/E+/Getty Images

Wisconsin Rapids

All aboard the Cranberry Highway in the cranberry capital of the world: Central Wisconsin. This part of the state produces 60% of the cranberries in the country. At the South Wood County Historical Museum in Wisconsin Rapids, you can see how the fruit was initially harvested by Native Americans, who also used its bright red pigment to dye fabrics. Then head to Historic Marker 86, where cranberry fields (that turn into bogs, come harvest time) stretch as far as the eye can see.

Do yourself a favor and stay at the Le Chateau The Manor (a bit repetitive, but whatever), a Victorian-style mansion turned B&B that serves the best breakfast you’ll find in town. Just ten minutes north is Rooted in Red, a multi-generational cranberry farm that’s been producing the tantalizingly tart berries for over 100 years. The farm just started offering bog tours in 2021 and, while no crop’s harvest season can be perfectly predicted, September and October offer the best chance of wading around in a sea of red berries.

If you have more time to spend in the area (and I hope you do!) head 25 minutes northeast to Stevens Point to check out the Stevens Point Sculpture Park and to have the best maple latte of your life at Ruby Coffee (their daily quiches are also pretty fantastic). Forty-five minutes west is Jurustic Park, an outdoor museum of prehistoric-inspired sculptures made from scrap metal, old cans, bicycle parts, and whatever the 84-year-old artist and amateur paleontologist, Clyve Wynia, found at the scrap yard recently.

That's a lighthouse I would very much enjoy living in. | Matt Anderson Photography/Moment Open/Getty Images

Door County

If Wisconsin were a hand, the Door County peninsula would be the thumb. Known as the Cape Cod of the Midwest, Door County is one of the most popular weekend vacation destinations for Wisconsinites, Chicagoans, and all visitors to the mid-best (not a typo). Summer fields of lavender make way for fire-red foliage in fall, followed by blankets of snow. This 70-mile long peninsula has 300 miles of shoreline that attracts swimmers, kayakers, and even scuba divers.

Nowhere else in Wisconsin will you find four phenomenal state parks so close to each other, all offering distinctly divine experiences. The caves in Whitefish Dunes State Park are best accessed by kayak, while Peninsula State Park (which can get quite crowded) is best for hiking. Newport State Park should be explored at night, as its International Dark Sky status means fantastic stargazing. For a much more remote experience, catch one of two ferries from Washington Island to camp in Rock Island State Park. Don’t like camping? Be sure not to miss the last ferry, since you won’t find any hotels on the island.

Anybody in the mood for some rock climbing? | Unsplash/Jonathan J. Castellon

Wisconsin Dells

Known as “the waterpark capital of the world,” the Wisconsin Dells draws in huge numbers of families and can get quite touristy, especially downtown. However, as an adult I’ve come to see the beauty of the surrounding nature here, which first attracted the crowds (many of them joining an Upper Dells river boat tour, which is actually quite beautiful). There’s still plenty of nature that’s quieter and less-crowded than the main drag. And you can find decent (and decently-priced) food at the indoor food truck park, Grateful Shed. Locals and tourists munch on jalapeño popper grilled cheeses and Fruity Pebble marshmallow ice cream sandwiches, while enjoying a concert or a game of bingo.

The Dells is also a great place to base yourself to visit state parks in the area. Mirror Lake State Park is a ten-minute drive away that has short, mostly-flat hiking year-round and calm kayaking on the lake in the summer. About 25-minutes south of The Dells is Devil’s Lake State Park, arguably one of the most beautiful parks in the state. Hiking, biking, camping, and rock climbing are all popular here, but the park’s claim to fame is the Devil’s Doorway rock formation. A half-mile trail requires some scrambling up rocks and stone-carved steps, leading to a tower of giant boulders balanced in an impossible, mother-nature-is-epic kind of way.

Frank Lloyd Wright's former home and studio sure is nice. | Taliesin Preservation

Spring Green

Two hours west of Milwaukee is the village of Spring Green, known for the American Players Theatre, an outdoor theater that puts on the best Shakespearean performances in the state. About a mile from the theater is Taliesin, the 800-acre former home and studio of Frank Lloyd Wright that is now a National Historic Landmark and UNESCO World Heritage Site (offering guided tours of the estate).

Ten minutes southwest of the manicured lawns and conservative (in comparison) architecture of Taliesin is what began as a lofty retreat, now turned into one of the most unique attractions in the state. The House on the Rock was the dream (or, possibly, acid trip?) of Wisconsin architect, Alex Jordan, who, quite literally, built the house on top of a rock. The enormous home hangs off a cliff, seemingly supported by nothing at all. The most shocking part of the home, however, isn’t the architecture or beautiful outdoor aesthetics, but rather, the wacky labyrinth of seemingly endless rooms with eclectic collections inside. You’ll see displays of everything from a 200-foot-long whale to enormous, coin-operated, self-playing music machines to 6,000 santas come Christmas to the world’s biggest carousel. Exploring the home while experiencing an altered state of mind isn’t required, but it also doesn’t hurt.

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Cassandra Brooklyn is a freelance writer, guidebook author, and the founder of the boutique travel company, EscapingNY. She specializes in all things outdoors and her work can be found inNational Geographic,The Daily Beast, andLonely Planet. Follow her on IG at @escapingny.