Chase the Chill: Midwest Winter Vacations Perfect for Families

Are you looking for some of the best Midwest winter vacations to take with your family during the upcoming season? Look no further! The Midwest transforms into a winter wonderland during this time of year, offering a picturesque setting for your holiday getaway.

There’s no shortage of winter activities, from charming small towns adorned with festive decorations to sprawling ski resorts and ice skating rinks. Whether you’re seeking adventure on the slopes, cozy evenings by the fireplace, or simply the magic of a snowy landscape, the Midwest has it all.

So, bundle up and prepare for an unforgettable family vacation filled with holiday cheer and winter fun in the Midwest.

Duluth, Minnesota

One of the most beautiful places in Minnesota is Duluth, located right along the shoreline of Lake Superior. Duluth becomes the ultimate destination for outdoor fun and holiday celebrations during the winter months.

In December, you can visit the Bentleyville Tour of Lights. This is the largest light show in Minnesota, with over five million Christmas lights. Plus, you can meet with holiday characters, enjoy free hot cocoa, and even roast a marshmallow.

If you’re a winter sports lover, then Duluth is perfect. Spirit Mountain and Lutsen Mountain ski resorts are open and buzzing this season. Or, you can try snowshoeing, cross-country skiing, or dog sledding along the North Shore.

You’ll also find endless hiking trails on the North Shore that are perfect for getting out in the winter. My favorites are Shovel Point and High Falls.

Door County, Wisconsin

Door County is a popular spot in Northern Wisconsin year-round, but during winter, there are so many fun things to do for all sorts of people. 

One of the best things to do is to check out Peninsula State Park. This beautiful park sits right on the edge of Lake Michigan and offers some great space to get outside. There are trails scattered around for snowshoeing or cross-country skiing. Or you can hike on the trails and enjoy the solitude.

Even just enjoying the views of the frozen water around the lake is a great way to enjoy Door County in winter! The caves and rugged cliff faces make for an even more beautiful site.

If you’ve spent enough time outdoors and need to warm up, head to one of the local breweries or coffee shops. There are a few of them in town, including many local restaurants.

Hocking Hills, Ohio

This beautiful Ohio destination is known for its waterfalls and great Midwest hiking. But in the winter, it becomes even more unique, thanks to its frozen fall and icicle-covered caves.

Cedar Falls, Ash Cave, and Old Man’s Cave are some of the most stunning hikes in Hocking Hills State Park. You may need a pair of microspikes to prevent yourself from slipping, but these trails are very doable in winter!

Skygazing is also popular in Hocking Hills, thanks to its dark skies. The John Glenn Astromony Park is one of the best places to see the stars or watch for the northern lights. Hocking Hills is another great place for winter vacations in the Midwest.

Marquette, Michigan

If you love winter activities, specifically snowmobiling and downhill skiing, then a Midwest winter vacation to Marquette, Michigan, is for you!

Marquette is located in the Upper Peninsula of Michigan, which gets a massive amount of snow yearly. This makes it the ultimate location for brushing up on your skills or fitting in your favorite hobbies.

The best place for skiing and snowboarding is the Marquette Mountain Resort, where you’ll find 25 runs to soar down.

There are also miles of trails around the Upper Peninsula to take a snowmobile. If you don’t have a snowmobile, there are rental places around that you can rent from. 

Minneapolis, Minnesota

As one of the largest cities in the Midwest, the fun winter activities in Minneapolis are endless, whether you’re looking for outdoor fun or holiday cheer!

The winter sports in Minneapolis are abundant. You can downhill ski at the many resorts within a short distance of the city, snowshoe and cross-country ski at the parks, or go snowmobiling on the trails.

And for the holidays, Minneapolis goes all out. Events are happening all December, from the GLOW Holiday Light Festival to the European Christmas Market.

Other fun events, like the U.S. Pond Hockey Championships, Ice Castles, and the Loppet Winter Festival, also occur in winter.

Chicago, Illinois

Chicago is always a busy city, but it comes alive during winter! There are many amazing things to do, from celebrating the holidays to shopping and cuddling inside, away from the cold.

Ice skating in Downtown Chicago is one of the top activities in winter. The best place to go is McCormick Tribune Ice Rink, located in Millenium Park, next to The Bean.

Watch the official tree lighting in Chicago for holiday celebrations and visit the Christkindlmarket in December.

If you’d rather stay indoors, see Chicago and Lake Michigan from above by looking down from Skydeck Chicago. Or you can check out the many local restaurants and grab a hot, fresh Chicago-style pizza.

Frankenmuth, Michigan

Frankenmuth is one of the best destinations if you’re looking for the perfect holiday vacation in the Midwest. With lights strung on every tree, horse-drawn carriages prancing down the street, and holiday tunes playing everywhere you go, this winter wonderland is perfect for all Christmas lovers.

Frankenmuth is known as Michigan’s Little Bavaria, thanks to its unique architecture that looks like it’s from Europe, which makes it even easier to create a magical holiday atmosphere in winter.

Activities like seeing the 40-foot lit-up singing Christmas tree, taking a driving lights tour, and skating on the ice rink are just a few ways to celebrate the holidays here. Plus, there are dozens of stores to stop in and grab a few last-minute gifts!

Baudette, Minnesota

This small town is found on the Canadian border of Minnesota and isn’t often found on people’s lists of places to visit. But its seclusion and quiet is what makes it so unique.

Baudette is found right on Lake of the Woods, one of the largest lakes in Minnesota. It’s known for its walleye fishing and is a busy place for boaters all year round.

In the winter months, when the lake is frozen, you’ll find that Lake of the Woods almost looks like it has its own little city because of all of the ice fishing houses that are on it.

Along with ice fishing, many people love snowmobiling on the lake, and you can reach the northernmost point of the contiguous US by snowmobile.

Medora, North Dakota

North Dakota isn’t often a place that is on people’s bucket lists, but the small town of Medora is more than worth the visit.

It’s the gateway to Theodore Roosevelt National Park, home to North Dakota’s Badlands. You’ll also find roaming bison, which look like the toughest animals on Earth when snow covers their faces!

You can enjoy live music and shows celebrating the holiday season at the Old Town Hall. Or you can wander the small shops and see all the local goods.

Another unique experience is to visit the Rough Riders hotel for their Old Fashioned Cowboy Christmas event. Here, you can enjoy Theodore’s Dining Room and live entertainment.

Bayfield, Wisconsin

Bayfield is one of Wisconsin’s most beautiful destinations for year-round travel. It’s located along the shoreline of Lake Superior at the very northern tip of Wisconsin.

Right offshore, you’ll find the Apostle Islands, a popular place to visit in summer. But during winter, you can see these islands and the sea caves on the rugged shoreline differently. You can walk along Lake Superior and explore the frozen Lake Superior caves in the right conditions!

You can also take the Ice Road from Bayfield to Madeline Island when the conditions allow. It’s such a unique thing to drive on a frozen Lake Superior!

Other fun activities include dog sledding, downhill and cross-country skiing, and ice fishing.

Mackinac Island, Michigan

While Mackinac Island is a buzzing summer vacation spot with charming buildings, horse-drawn buggies, and delicious fudge, it’s also an excellent spot for a Midwest winter getaway.

The ferry still takes visitors to the island in winter, and you’ll have a pretty quiet and peaceful visit since there will be fewer visitors than in summer!

Visiting Mackinac Island State Park is a great way to spend your time. Some of the visitors’ great activities are hiking, fat tire biking, and cross-country skiing.

You can also still get around on horse-drawn carriages, which feels like you’re in a winter wonderland, mainly since Mackinac Island receives quite a bit of snow in the winter! 

There are minimal stores open during winter, but if you’re an outdoors lover, you’ll love visiting Mackinac Island in the winter.

Branson, Missouri

If you aren’t an outdoor traveler but still want to get away in the Midwest this winter, plan a trip to Branson, Missouri. 

This beautiful town is known as the ‘Live Entertainment Capitol of the World’ because of the many shows and performances around the city.

You can watch all the performances and a live show or two when it’s chilly outside. There are all sorts, including dinner shows and shows specific to Christmas.

A few of the most popular include Dolly Parton’s Stampede, The Haygoods, and anything at the Little Opry Theatre.

If you want to spend some time outdoors, you can still check out the Ozarks surrounding Branson, which is beautiful when covered in snow.

Black Hills, South Dakota

South Dakota is an often overlooked state, but many stunning locations exist, especially in the western half.

Getting out and enjoying the endless activities that you’ll find in the Black Hills gives you the chance to embrace the winter season.

There are many scenic drives, such as the Spearfish Canyon Scenic Byway and the Wildlife Loop Road in Custer State Park. These are beautiful in winter when the snow is freshly fallen, and you can watch for wildlife as you drive.

The Terry Peak Ski Area is a great place to hit the slopes and enjoy the beautiful views around the Black Hills. Or, you can enjoy the outdoors in another way, such as snowshoeing or snowmobiling. 

Other fun activities include visiting the small Wild West town of Deadwood or exploring the Mount Rushmore National Memorial.

Family Winter Vacations in the Midwest

Traveling somewhere new for the winter is always fun, and even if you want to stay close to home, there are many great places to get out. These Midwest winter getaways are a great way to celebrate the holidays, enjoy the outdoors, and escape for a little bit.

This article originally appeared on Wander With Alex. Photo Credit: [@d.travnikov/DepositPhotos]


Chase the Chill: Midwest Winter Vacations Perfect for Families
Kassidy Olson

Kassidy Olson is a Minnesota native who loves spending her time exploring her home state and beyond. She loves sharing her adventures over on her blog, Kassidy's Journey.