7 Memorable Midwestern Winter Getaways For Families

by | Nov 22, 2022 | Family Adventures, Midwest, USA, Weekend Trips

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Visiting the Midwest in winter is not for the faint of heart, or at least not for those who don’t own snow boots. When I moved to Cleveland for college and my Clevelander cousin told me I needed knee-high snow boots, I thought she was exaggerating. She wasn’t.

Despite the cold, these midwest destinations are still a perfect place to worth a visit for winter vacation. In fact, if you summon your courage and visit the snow-covered cities of the Midwest for a winter vacation in winter, you’ll find that the snow and winter weather actually make these destinations more magical!




Cleveland, Ohio 

I have to start with Cleveland, my home away from home. Cleveland is one of the best places because of the quality and quantity of museums there: a perfect winter activity!

Cleveland is famous for being home to the Rock and Roll Hall of Fame. At the Rock Hall you can pay your respects to legends like Prince, the Beatles, and more. Your kids will like the current music section, where they will find memorabilia from today’s artists. The entire family will enjoy the Power of Rock experience, featuring music from induction ceremonies and a ton of fog machines.

The Cleveland Art Museum is world-class and FREE. They have an extensive Asian artwork collection, an impressionist collection, and many other works.

While you’re  in town, stop by the Christmas Story House! You can tour Ralphie’s bedroom, get a chance to hide in the kitchen cabinets, and try your hand against Black Bart (or at least pretend to). Just don’t curse or you’ll end up trying Lifebuoy soap. If you’re looking to switch careers and move to Cleveland, you’ll be happy to know that the house is currently for sale and it can fit your entire family.

Want to pretend to be a VIP while in Cleveland? Stay at The 9. That’s where all the professional sports teams stay when they are in town, so you might get to rub elbows with Joe Burrow if you time it right.


The Rock and Roll Hall of Fame in Cleveland, Ohio.


Don’t Miss! Most Awesome Things to Do in Cleveland with Kids 


Detroit, Michigan 

Detroit also makes the list for its awesome museums in the United States! Detroit is home to the Henry Ford Museum, a HUGE museum dedicated to, well, just about everything. Plan a full day here. Maybe more than one day. Henry Ford also gets exceptional seasonal exhibits, so make sure you check their schedule! Don’t miss the Rosa Parks bus, an important educational opportunity for your entire family kids.

While you’re in town, stop by the Motown Museum! It’s a small museum but definitely a great option; an afternoon is plenty of time, but it’s still worth a stop! The exhibits upstairs rotate but always feature Motown’s most famous artists. You’ll finish your tour with a visit to the recording studio downstairs. (Accessibility note: the Motown museum does not have an elevator).

When we were in town, my family stayed at the Towneplace Suites in Dearborn because of its proximity to the Henry Ford Museum.


The Motown Museum and the famous recording studio in the basement are must-sees on your vacation itinerary.

The Motown Museum and the famous recording studio in the basement are must-sees on your vacation itinerary.


Door County, Wisconsin

Another not to miss midwest winter getaway for families is Door County, Wisconsin. Door County is a string of small towns on a peninsula bordering Lake Michigan and Green Bay. It’s mostly a summer and spring tourist hotspot but even in the winter, there are plenty of fun family activities. Take a naturalist-led guided hike, with snowshoes if you’re lucky, through the Ridges Sanctuary, the most biologically diverse spot in all of Wisconsin. Another great place for outdoor activities is Peninsula State Park. Climb the all-abilities accessible Eagle Tower through its ramps or  95 steps. Eagle Tower is 60 feet high and provides a carpet view of the trees covering Peninsula State Park and a clear shot to  Horseshoe Island. Then enjoy the roughly two-hour Eagle Trail that takes adventurers past caves and ominous-looking cliffs. Don’t forget your waterproof pants because Peninsula State Park is also the place for cross-country skiing, snowshoeing, ice fishing, snowmobiling, sledding, and tubing!

If you go in February, check out Fish Creek’s Winterfest, the quirky celebration of a diverse community. There’s live entertainment, a Fruit-Loop run, a chili cookoff, and cherries, of course.

Stay at the Landing Resort with a kitchen and rooms that feel more like apartments than hotels. Our room had a back patio with a verdant lawn leading to a small grove of trees. There is also an indoor pool and breakfast included.


snowy lake - best winter midwest getaways

Icy Calm  Photo by Dominik Dombrowski on Unsplash


Wisconsin Dells

Who says you can’t enjoy the water in the dead of winter? Not innovative Wisconsinites! Wisconsin Dells is considered the “waterpark capital of the world.” There are more than 200 waterslides in Wisconsin Dells and 16 million gallons of water push family travelers through the Dells’ favorite heated spots. Seventy acres of waterslides, including one that loops, and a lazy river makes Noah’s Ark America’s largest outdoor waterpark.  The Wilderness Resort is America’s largest indoor-outdoor combination waterpark. It has a 180-foot-long slide, bumper boats, a wave pool, spa and golf course. There is also the Kalahari Resort, Wisconsin’s largest indoor waterpark. Thrillseekers will love its 250-foot-long slide and the wave simulator for indoor bodyboarding and surfing. The is also a Great Wolf Lodge there with a whole Snowland program for winter fun. That’s also the place where we’d recommend your family should stay. There are quests and arcades and so many fun indoor experiences that you’ll forget it’s a tundra right outside!


boy on boogieboard in wave pool - midwest winter getaways

Just like the real thing…only safer! © Rina Nehdar


Minneapolis, Minnesota

The Mall of America puts Minneapolis on the map, at least a shopping map. Do your holiday shopping at the biggest mall ever, which is similar to many theme parks! Kids will love the Nickelodeon-themed rides, and it is a perfect family vacation. Good luck getting them out of that place! They even have an indoor waterpark with hot tubs and indoor pools! I’m convinced they built a huge mall in Minnesota because it’s so cold there most of the year, making you want to hide inside! If you’re stuck inside, what better to do than shop?Pro-Tip: If you’ve never driven in the snow, I have a tip for you. Don’t slam on your brakes! Just drive slowly and carefully. 

Want to try your hands at some winter sports? Visit Theodore Wirth Park and try out cross-country skiing, snowshoeing, sledding, tubing, ice skating and more outdoor adventures! You can avoid overweight/oversize baggage charges by renting your gear from the park.

I recommend the JW Marriott because it’s connected to the Mall of America. You can drop off your new goods at your room when your arms get tired.


The Mall of America in Minneapolis is a great Midwestern destination for the winter: everything is indoors!

If you can’t find it at the biggest mall in the world, it probably doesn’t exist. Photo Courtesy of Farragutful, via Wikimedia Commons.


Keystone, South Dakota

If you’ve never heard of Keystone, South Dakota, I don’t blame you. Just 250 people live there as of the last census. But Keystone has an important purpose: it’s the gateway to Mount Rushmore and the Black Hills.Why visit Mount Rushmore in the winter? Well, low crowds for one. Most people don’t venture to an outdoor attraction in the winter. Plus you’ll have a chance to see Mount Rushmore covered in snow, a beautiful sight to behold during your winter vacation. Additionally, you can enjoy yourself while ice fishing in Lake Horsethief, which is only 4 miles away from this historic monument!

While you’re in town, take your kids to see the ongoing construction at the Crazy Horse Memorial. Once it’s completed, it will be the second-tallest statue in the world! It’s also a great opportunity to learn about Native American history. 



Nearby Custer State Park is also excellent to visit in the winter. The snow scares most visitors away, so you’ll have the park to yourself! It is one of the best state parks for wildlife viewing during this time of year! Just make sure to check a map; depending on snowfall there may be seasonal road closures. Most of the fun things to do in the park, including their famous jeep tours, are available in the winter, but call ahead to confirm availability.

I recommend the K Bar Lodge when visiting the Keystone area because of the beautiful views of the surrounding mountains.


The main street of Keystone, South Dakota, looks a bit like a Hallmark holiday paradise with its historic, old buildings.

Keystone looks like something out of a Hallmark movie. (Be careful that no one asks you to save an inn or enter the town baking contest.) Photo Courtesy of TravelingOtter, via Wikimedia Commons


Pittsburgh, Pennsylvania

I might be cheating by including Pittsburgh. I don’t think it’s “technically” considered a midwest weekend getaway. But I’m including it because it’s a great time beautiful city to visit in the winter! 

Kennywood Park hosts a wonderful winter program: you can visit a petting zoo, meet Santa, and ride the 102-year-old Jack Rabbit coaster. (How many people can say they’ve ridden a 102-year-old roller coaster?) Kiddieland and other historic rides, such as the Auto Race which is the last of its kind, are usually open to enjoy as well. 

Don’t miss the Duquesne incline, one of the few remaining inclines of its kind. It’s a historic cable car, used to get workers up and down Mount Washington before cars were common. You can ride to the top for just a few dollars. You’ll be treated to a gorgeous view once you get to the top! Your kids will definitely be impressed by this one-of-a-kind ride. The top of Mount Washington is an incredibly popular place to propose, so be on the lookout for happy couples. 

If you’re a Mister Rogers fan, be sure and stop by the Pittsburgh Children’s Museum. They have lots of exhibits that pay respect to our favorite neighbor; after all, he was a Pittsburgh native!


Don’t Miss! Best Things to Do in Kennywood for Families!


Pittsburgh also has a lot of seasonal festivals. Be sure to check out visitpittsburgh.com for the schedule!

Just outside the city is the 7 Springs Ski Resort. 7 Springs has plenty of family-friendly skiing slopes, cross country skiing, and snowboarding, but my mom and I prefer the world-class spa and hot tub during this time of year.

I recommend staying at the Sheraton at Station Square because of its easy proximity to shopping and dining.


A bridge spanning across a river near Pittsburgh, PA.

Pittsburgh has the second-most number of bridges in the world, after Venice. It’s no wonder with 3 rivers! Photo by Emily Householder Stacey.


No matter which Midwest city you pick this winter, be sure to pack some snow boots! And trust me, a packable winter jacket is also a good investment for frequent winter travelers. If you do have to drive in the snow, just remember to pretend that your grandma is riding with you and she’s got a crock pot full of soup on her lap. Drive slowly and carefully and you’ll be just fine!




Emily Householder Stacey is a travel agency owner and travel writer based in the birth place of professional football: Canton Ohio. This time of year, you’ll typically find Emily snuggled up with a good book and a cup of peppermint hot chocolate.