November 1, 2025
10 Midwestern Escapes to Enjoy This Winter

10 Midwestern Escapes to Enjoy This Winter

Sure, you have to bundle up when the winter weather arrives, but you can also enjoy some of these midwestern escapes when you want to get away.

Whether you go for a weekend or take your holiday vacation at one of these amazing locations, you’ll be glad to travel to a place that turns winter into a wonderland. Bring some warm clothes and get ready to explore what the Midwest has to offer when you’re traveling during the colder months of the year. Winter never felt quite as good as it does at some of these amazing locations.

Check Out the Covered Bridges of Parke County, Indiana

The Hoosier State might not be the first place you think of for your winter adventures. This state is basically flat and covered in cornfields, but there are some hidden gems. Parke County offers various covered bridges that can make for some of the most impressive holiday card scenes or simply give you a quiet place to enjoy. Enjoy some hiking and driving through this amazing county where many people don’t come to visit, but you’ll find something special.

Hike Along the Shoreline in Door County, Wisconsin

Door County is one of the most popular places to visit in Wisconsin, and that doesn’t change when the colder months arrive. If you’re looking for one of the most enjoyable midwestern escapes during the winter, you’ll want to head to this area of Wisconsin. This county is considered the Cape Cod of the Midwest with its shorelines and amazing trails. Get ready for some cozy time at the inns, incredible shops, and hiking that makes this a wonderful place to go.

Visit a Few Cool Places in Omaha, Nebraska

Omaha is a large city, which means it offers some great activities for every time of day. Thankfully, this city also brings the wonders of winter into many outdoor activities. Admire the beautiful holiday decorations, visit Lauritzen Gardens, the Henry Doorly Zoo, or the Durham Museum. There are many ways to enjoy your winter escape in Omaha; find the right places to go and the events taking place during the colder months of the year when you visit this beautiful city in the Midwest.

Imagine Hiking the Black Hills of South Dakota

There’s no denying the harsh forces of winter find their way to South Dakota every year. Hiking around in the Black Hills can be a lot of fun for you. If you want to enjoy some winter activities, rent a snowmobile or set of cross-country skis and enjoy the fun of going through the snow-covered pine trees. Heading to this area of South Dakota can be one of the best midwestern escapes during the winter months. Get ready for some outdoor fun in a wonderful landscape.

Visit the Wineries of the Old Mission Peninsula and Traverse City in Michigan

This area of the state, shaped like a mitten (winter was always meant to be here), is littered with amazing wineries and cool places to visit. Enjoy some of the winter wines, which are usually sweet ice wines that offer a wonderful flavor series that you’re sure to enjoy. Traverse City is in the lower part of the Peninsula and offers various lodging options, making it easy to turn this adventure in a winter wonderland that you’re sure to remember for many years.

There’s a Lot to do in Brainerd, Minnesota

Brainerd is about two hours north of Minneapolis and offers some wonderful deep snow that makes it fun to enjoy some amazing winter activities. If you love to ski, snowboard, hike, or skate, you’ll find it here. This area is easily one of the best midwestern escapes in winter, offering you some of the most amazing fun you’ll find during the colder months of the year. Book your trip now; you might want to stay longer than a weekend.

Check Out the Beautiful Views at Bayfield, Wisconsin

There’s one thing you want to head to the tiny area of Bayfield to see. Out on Lake Superior, you can see the Apostle Islands frozen in the lake. Some years the lake is frozen solid enough for cars to drive out to Madeline Island, where you can explore the caves of the island. If you’re looking for something fun to do during winter that’s different from what you normally experience; you’ll love heading to Bayfield, Wisconsin.

Branson, Missouri is Known for its Winter Offerings

Branson is well-known as a place to go in the middle of the country. During the warmer months, it’s a place with lots of activity and fun. In the winter, the fun is still pretty strong, with lots of winter landscapes that are amazing to see. If you’re looking for one of the most incredible midwestern escapes to enjoy this winter, head to Branson and experience the fun offered. You can walk down the decorated streets, duck into the shops, and admire the wonderful beauty of the winter world around you.

Enjoy a Romantic Getaway in Canoe Bay, Wisconsin

If it’s time for you and your partner to reconnect, one of the best places to go in the winter is Canoe Bay, Wisconsin. This location is in the northwest part of the state and offers a variety of plush cabins, gourmet restaurants, and horse-drawn sleigh rides. This is a wonderful want to enjoy connecting and celebrating the special relationship you have together.

Enjoy a Pampered Getaway at Crystal Mountain, Michigan

Crystal Mountain is a ski resort southwest of Traverse City that has become a wonderful destination for those looking for the best ways to enjoy winter. You’ll love this location as a midwestern escape in the winter and want to return every year for some more fun. There’s a lot of amazing food offered on the menus of various restaurants; enjoy the incredible 11,000-square-foot Crystal Spa, and fall in love with the lodges and shops in the area. You can ski right out of your back door in this city which puts you on a mountain that you’ll love to visit year after year.

Does one of these midwestern escapes sound great for your winter fun? If so, book your trip now and get ready to enjoy the cold and frostiness that comes with the beauty of winter.