Want to Make the Most of Winter? Take a Cue from These Midwestern Cities

Bring it, snow.

The Midwest is as famous for its brutal winters as it is for its generally nice people. But shouldn’t the two be at odds with one another? How do you stay chipper when you’re in the eye of a polar vortex? It turns out Midwesterners have spent generations finding ways to not only coexist with the winter, but to actually own it. The cold weather isn’t a hindrance: It’s a cause for creative celebration.

The below Midwestern cities and small towns bring their A-game to the winter. Not only do they offer excellent experiences for cold weather adventurers, but they also turn up the fun factor in a serious way, offering up great festivals, luminescent art installations, cozy winter villages, and quirky local traditions that pair well with their already stellar food, drink, and entertainment. Bundle up and get ready to embrace the winter among the Midwest’s best destinations for a cold-weather getaway.

minneapolis skyline in winter
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Minneapolis, Minnesota

It’s pretty hard to find a better Midwestern winter destination than the largest city in Minnesota—a state with no shortage of great things to do during the long, cold winters. After all, locals fully embrace the cold and take advantage of a slew of cool (pun intended) seasonal activities.

Chief among them is the Great Northern Festival, an annual  winter extravaganza that goes down in late January. During the 10-day festival, you’ll find live music, art installations, chef-driven food experiences, foot golf, fire pits, climate talks, an ice bar, the US Pond Hockey Championships, and skijoring—which is basically dogsledding without the sled. Bold North, indeed.

pouring beer at Beer Dabbler festival
Beer Dabbler

While the Great Northern is king on the festival front, other seasonal events like the Winter Beer Dabbler and Vikings Winter SKOLstice make for a fun cold-weather visit to the City of Lakes. Travelers should also consider a snowshoe tour of the Walker Art Center, including its iconic Spoonbridge and Cherry sculpture.

After that outdoorsy fun, warm up at the new Watershed Baths & Spa, a first-of-its-kind, holistically minded communal bathhouse. On the dining side, for an especially luxe winter meal, check out the private rooftop cabins at the Four Seasons Hotel Minneapolis, dubbed the Nordic Village at Riva Terrace.

traverse city michigan lake in winter
Photo courtesy of Traverse City

Traverse City & Petoskey, Michigan

Best known for its stellar wine and cherries, Traverse City (a.k.a. the pinkie finger on the mitten that is of Michigan’s Lower Peninsula) is a legit winter haven. Many of the area’s famous wineries have unique offerings during the slow season, like snowshoe trails between vineyards, roasting s’mores around a communal fire pit, and the annual Ice Wine Dinner at Chateau Chantal, held as part of Ice Wine Weekend hosted by the pioneer of cold climate viticulture.

While there, don’t skip the nearby Sleeping Bear Dunes National Lakeshore and its towering sandscapes open up for special hikes during the season. The super popular Pierce Stocking Scenic Drive is closed to vehicles and instead open for cross-country skiing, hiking, and snowshoeing.

Downtown Petoskey in winter
Downtown Petoskey

Meanwhile, a spectacular 90-minute drive along one of the nation’s most scenic shorelines away you’ll find another great winter escape: Petoskey. The town, named after the famous Michigan-only stones, is  a former Hemingway haunt (his family still has a lake house in the area). The annual Petoskey Holiday Open House is a winning option, especially since a special liquor license allows for strolling outdoors with an adult beverage or four.

During this fest, the downtown streets are transformed into a pedestrian hub and merchants stay open late for holiday shopping fueled by mulled wine and spiked hot cocoa. Afterwards, check out the Enchanting Trail in adjacent Harbor Springs, a two-mile snowshoe hike through a mesmerizingly illuminated forest to a cozy yurt.

cleveland skyline in winter
Dee/iStock/Getty Images Plus

Cleveland, Ohio

There’s much more to this lakeside city than the Rock & Roll Hall of Fame and the famed Christmas Story house. Downtown comes to life all season long with the annual WinterLand celebration—think ice skating, concerts, fire pits, the works. Then get your adrenaline pumping on the toboggan chutes at Mill Stream Run, where riders can rocket down the state’s tallest ice chutes (700 feet, woohoo).

Best of all, just outside the city is Cuyahoga Valley National Park, which earns winter wonderland status with its snow tubing, downhill skiing, snowshoeing, and ice hiking. Warm up with a glass of wine crafted from Ohio-grown grapes at the winery INSIDE the park.

Two other annual offerings are a wintertime draw; visitors can commemorate Martin Luther King Day at the Ice Fest at North Coast Harbor and its more than 40 ice sculptures, live ice-carving demo, and complimentary hot cocoa. Or get down at a full-day music and illumination festival during February’s Brite Winter in the Flats neighborhood.

downtown chicago in winter
tunart/E+/Getty Images

Chicago, Illinois

The Windy City is pure magic in the summer, but don’t be turned away by the constant talk of the brutal winters—Chicago shines bright even during the coldest months. Get a taste of traditional German Christmas markets stateside at the annual Christkindlmarket Chicago celebration. Skate on the ice rink on Wrigley Field (or by "the Bean" in Millennium Park for any Cubs haters). Additionally, Chicago lights up with Lightscape at the Botanic Garden, Illumination: Tree Lights at The Morton Arboretum, and Holiday Magic at the Brookfield Zoo.

But perhaps the best reason to visit Chicago during winter is the festive pop-up bars. You could try a slew of options, such as the Fairmont Lodge, Winter Wonderland at The Godfrey Hotel, Rudolph's Rooftop at LondonHouse Chicago, Happy's: A Holiday Pop-Up Bar at the Chicago Athletic Association, or 8 Crazy Nights, Chicago's only Hanukkah-themed pop-up bar at The Graystone Tavern in Wrigleyville.

couple winter snow biking at Spearfish Canyon Lodge
Spearfish Canyon Lodge

Spearfish, South Dakota

Our pick for South Dakota’s best small town brings some serious heat to SoDak’s deeply unpredictable winter landscape, but it’s not just the welcoming bars and restaurants lining the Old West downtown that should bring you to Spearfish this winter. Perched on the western border of the state, this is the perfect base camp for exploring one of the most criminally overlooked winter destinations in the Midwest.

In Spearfish proper, you'll be rewarded frozen waterfalls and zig-zagging snowmobile trails alike, with the iconic Spearfish Canyon Lodge hooking up the gear rentals and comfy rooms all winter long. The nearby Custer State Park is home to the towering Needles Highway and the typically frozen beauty of Sylvan Lake. Head west to see a snow-covered Devil’s Tower just over the Wyoming border, or make the longer trek east to behold a stoically uncrowded Mount Rushmore or the ice-covered Badlands. Or just cruise over to nearby Deadwood and have your pick of the casino games without the bikers who descend upon the scenic town each summer for the Sturgis Rally.

public art in downtown milwaukee in winter
Milwaukee Downtown

Milwaukee, Wisconsin

Milwaukeeans have evolved, over the years, to not only survive the brutal Great Lakes winters. They’ve learned to thrive. It starts with some of the heartiest comfort foods on the planet (brats, curds, beer… you betcha!) served up at warm, friendly neighborhood bars that seem to be situated on every corner of the city. But it’s not just the bars, breweries, and mom and pop restaurants that keep things going around here: Milwaukee has a habit of coming to life once things get sub-zero.

Along with the requisite holiday festivals, the downtown area glows extra bright with Lightfield, which transforms Cathedral Park into an outdoor museum featuring 24 trippy light sculptures. Elsewhere, Red Arrow Park hosts a giant ice rink, the Boerner Botanical Gardens launches its own Winterfest, and you’ll find skiing and sledding at nearby Franklin’s The Rock Snow Park.

And because Milwaukee is Milwaukee, you’ll also find plenty of hoppiness at the Third Space Brewing’s Ice Beer Fest; morning libations at the annual Best Bloody Contest; and the Wückfinter Festival hosted by Ray’s Wine & Spirits, an outdoor event where you can combat winter by saying “wück it” and fill up on boozy beer slushies from iconic midwest brewer 3 Floyds.

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Katy Spratte Joyce is a contributor for Thrillist.