11 Midwest vacation destinations for a great winter getaway

11 Midwest vacation destinations for a great winter getaway

Travelers want to flock somewhere warm and tropical come winter, right? Not so fast—some of us want our magical, snowy scenes. If you’re anything like me, you enjoy winter and all the peace it brings, and one winter destination that’s always overlooked? The Midwest.

And what a mistake that is! Winter transforms the Midwest’s vacation places into glowing, holiday-spirit-filled getaways. From snowy landscapes perfect for outdoor sports to charming towns embracing Christmas joy, check out the Midwest vacation locations below for that memorable (and cozy!) winter getaway.

Cave Point County Park, Door County, in winter

Cave Point County Park, Door County, in winter

1. Door County, Wisconsin

Why Door County is one of the best Midwest vacation destinations: 80+ miles of shoreline, accessible waterfront, great cuisine

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Known as the “Cape Cod of the Midwest,” Wisconsin’s Door County shines in winter with its waterfront villages, frozen shorelines, lighthouses, and cozy inns. Snowshoeing, cross-country skiing, hiking, and ice fishing attract outdoor folks—or, if you just like looking at pretty places, the cliffs of Cave Point County Park, pictured above, are an absolute must. Everyone else seeking warmth can hide in the sea of restaurants, museums, supper clubs, and diners.

Go beyond larger towns like Sturgeon Bay and Sister Bay into villages like Fish Creek and Ephraim, where you’ll find boutique shops, art galleries, and warm cafes. Try a traditional fish boil for a taste of local culture or pop into a supper club, like Nightingale Supper Club (111 years running!), for the classic, only-in-Wisconsin experience. Ice-cream drinks, anyone?

Marquette, Michigan, one of the best Midwest vacation destinations

Sugarloaf Mountain in Marquette, Michigan

2. Marquette, Michigan

Why Marquette is one of the best Midwest vacation destinations: A fabulous cafe and brewery scene, great lake views, excellent hiking, a picturesque downtown

The largest town on Michigan’s wild Upper Peninsula, Marquette is just plain gorgeous. The town sits on the hilly, forested shores of Lake Superior—take in the pretty waterfront right from downtown or on the shorefront multi-use path, or head for the trails up in the hills. Spots like Sugarloaf Mountain, above, offer great 8AM winter sunrises.

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Outdoors-wise, explore the Noquemanon Trail Network for world-class cross-country skiing and fat-tire biking, or try ice climbing at the Eben Ice Caves. Marquette Mountain Resort offers skiing and snowboarding opportunities for all skill levels, too. After a day outdoors, warm up in one of the city’s craft breweries, like Ore Dock Brewing, or cozy cafes, like Babycakes. Washington Street comes loaded with idyllic main-street vibes—there’s even a candy shop, Doncker’s, that’s been running for 120+ years.

Galena, one of the Midwest's best vacation locations

Main Street, Galena, Illinois

3. Galena, Illinois

Why Galena is one of the best Midwest vacation destinations: 200 years of history, Hallmark vibes for days along Main Street, great B&Bs

Galena’s historic charm is amplified in winter, with its well-preserved 19th-century architecture and curving, often-snow-covered streets. Ski or snowboard at Chestnut Mountain Resort, then return to town for boutique shopping and gourmet dining, like at Bread and Vine or Fried Green Tomatoes. History buffs and architecture nerds will likely enjoy President Grant’s home and the 1826 Dowling House, the oldest house in town.

As for lodging, cozy bed-and-breakfasts—like Cloran Mansion—make Galena one of the most romantic Midwest vacation locations for couples seeking a winter escape. If there’s one spot in the Midwest that looks like a Hallmark card, it’s Galena.

 Stillwater, Minnesota, one of the great Midwest vacation destinations

Stillwater, Minnesota

4. Stillwater, Minnesota

Why Stillwater is one of the best Midwest vacation destinations: a historic downtown, river activities, hikes, serene vibes

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On the pretty St. Croix River, Stillwater is the “Birthplace of Minnesota,” a charming river town that turns into its most scenic self come winter (okay, fall is pretty great, too). The historic downtown gets adorned with twinkling lights, creating a festive atmosphere perfect for strolling, shopping, and dining, like at The Main Cafe or Brick & Bourbon.

Outdoors, there’s ice skating at Lily Lake and hikes along Brown’s Creek State Trail—or head a bit north to the gorgeous cliffs of Interstate State Park. Winter festivals, like the World Snow Sculpting Championship, add to the seasonal cheer. End your day by relaxing in a cozy riverside inn, like Water Street, or even one of the town’s restored mansions.

Yerkes Observatory, just outside Lake Geneva, Wisconsin

Yerkes Observatory

5. Lake Geneva, Wisconsin

Why Lake Geneva is one of the best Midwest vacation destinations: fun winter events, history, and a wide variety of things to do

Lake Geneva, a getaway town for the Chicago elite, offers the perfect blend of luxury and winter fun. Stay in upscale resorts with spas or explore the scenic, mansion-lined Lake Geneva Shore Path for a frosty hike (20+ miles!). The Winterfest festival, featuring the U.S. National Snow Sculpting Championship, is a highlight of the season.

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For indoor adventure, don’t miss Yerkes Observatory, home to the Great Refractor—the largest refracting telescope on the planet. And, of course, there are more Wisconsin supper clubs to try in this area, like Mars Resort. Whether you’re seeking relaxation or excitement or just to walk in the footsteps of Carl Sagan, this charming town is one Midwest vacation spot that delivers.

Traverse City, Michigan, one of the best Midwest vacation places

Joshua’s Crossing, Traverse City, Michigan

6. Traverse City, Michigan

Why Traverse City is one of the best Midwest vacation destinations: great lake views, great cuisine, plenty of options for accommodations and more

Famous for its summer-friendly wineries and cherry orchards, Traverse City also shines in winter. Tour local wine-tasting spots, hit the slopes at nearby Crystal Mountain Resort, or just partake in a winter classic: eating your weight in cherries and pie (check out the Grand Traverse Pie Company and Cherry Republic). All jest aside, there’s a reason chefs and sommeliers have flocked to this area for so long.

The waters of Lake Michigan are gorgeous up here in winter, too, especially around landmarks like the Grand Traverse Lighthouse, up the peninsula in Northport. There are great hiking trails, great fat-biking trails—there’s even winter ziplining. There’s a staggering amount of things to do here, and I haven’t even mentioned kissing the moose at Sleder’s.

Mount Rushmore National Monument in winter, Black Hills, South Dakota

Mount Rushmore National Monument

8. Black Hills, South Dakota

Why the Black Hills are one of the best Midwest vacation destinations: incredible scenery, so many national park sites, Wild West history

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South Dakota’s Black Hills region offers a unique winter adventure, blending natural beauty with cultural attractions. Explore Mount Rushmore’s majestic visage dusted with snow (away from the crowds!); head to the fabulous Custer State Park for wildlife spotting and scenic hikes; and hunt down the graves of Wild Bill Hickok and Calamity Jane. From the creaky saloons of Deadwood to the waterfalls of Spearfish Canyon, this is easily one of the prettiest spots in the Midwest, and one of the best Midwest vacation spots, too. There’s a reason cowboys loved it here, and in winter, you’ll get to experience it almost crowd-free.

9. Duluth, Minnesota

Why Duluth is one of the best Midwest vacation destinations: nice hikes, good breweries, lots of lake views

Situated on the shores of Lake Superior, Duluth transforms into a frosty snowglobe come winter. For the adventurous, try ice climbing at Gooseberry Falls State Park or skiing at Spirit Mountain; for something more leisurely, take in the spectacular Bentleyville Tour of Lights or tour Glensheen Mansion.

With a hot cup of cocoa, get on the Lakewalk for great views of the frozen lake, or head to one of Canal Park’s cozy cafes and shops (and cideries!) for warmth and charm. Then there are Duluth’s distilleries—Vikre is a personal fave. If you enjoy a nice gin, you’re in good hands in Duluth.

Wisconsin State Capitol, winter in the Midwest

Wisconsin State Capitol, Madison, Wisconsin

10. Madison, Wisconsin

Why Madison is one of the best Midwest vacation destinations: waterfront views, easy to get around, so much to do

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Madison combines urban sophistication with outdoor fun—I should know: I live here. The city’s four frozen lakes become playgrounds for ice fishing and skating, while local restaurants serve up farm-to-table fare and Wisconsin classics—definitely grab cheese curds and an old-fashioned, the state’s signature drink, at The Old Fashioned.

Visit the Dane County Farmers’ Market’s winter edition, stroll amongst the pines at the UW arboretum (once home to Aldo Leopold), and peruse the shops along pretty Monroe Street. If you can time it right, visit for the Winter Carnival, where the Statue of Liberty gets sunken into Lake Mendota. Try to stay on the isthmus—the land between two lakes—to get the signature Madison experience.

 Hocking Hills in winter, a great Midwest vacation destination

Hocking Hills in winter

11. Hocking Hills, Ohio

Why the Hocking Hills are one of the best Midwest vacation destinations: great and varied scenery, excellent trails, so many accommodation options

Hocking Hills State Park in Ohio offers exquisite winter landscapes with frozen waterfalls and snow-covered gorges. Popular hiking trails like Old Man’s Cave and Ash Cave are transformed into icy wonders, and in winter, it’s a much more serene experience—the area gets a whopping 4 million annual visitors, but most of that foot traffic happens in summer.

Cabins with hot tubs provide a warm respite after exploring (I call them hot-tub getaways), making Hocking Hills a favorite for those wanting outdoorsy but romantic Midwest vacation destinations. In terms of accommodations, the area is also rife with 2-bedroom cottages, treehouses, even hobbit and cave lodgings. There’s a little something for everyone here in them hills!

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