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10 Fun Day Trips from Milwaukee in Winter

Guide to the best winter day trips from Milwaukee for the whole family to enjoy

Are you planning to travel to Wisconsin during the colder season? There are so many day trips from Milwaukee in winter, making the city a perfect start to explore the Badger State.

As the largest city in Wisconsin, Milwaukee has its own charms for winter holidays. But on top of that, it’s pretty easy to arrange winter day trips from Milwaukee to make the most of your Wisconsin trip.

Not sure where to go? Here are some of the best winter attractions near Milwaukee!

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Overview: Top 5 Day Trips from Milwaukee in Winter

  • For another big city visit: Chicago
  • For fun with the whole family: Wisconsin Dells
  • For winter the best winter activities & events: Lake Geneva
  • For outdoor enthusiasts: Eagle
  • For foodie travelers: Kenosha

1. Lake Geneva

Best winter events in Wisconsin near Milwaukee, Large psychedelic snow sculpture of an older bald man with a long beard adorned with several large bowls containing planets and stars with a looping spiral above it

While the area is pretty popular during summer, Lake Geneva is also one of the best places to visit in Wisconsin in winter.

As one of the most popular winter getaways from Milwaukee, Lake Geneva is home to two popular ski resorts in Wisconsin: Wilmot Mountain and the Mountain Top at Grand Geneva Resorts.

Lake Geneva also hosts the famous Winterfest annually every February, which is one of the top winter events in Wisconsin.

It’s also, of course, one of the best things to do in Lake Geneva in February, and you wont want to miss it.

Not only is it one of the largest winter events near Milwaukee, but it’s also the place where you can enjoy the masterpieces from the best ice sculptors around the country!

There are so many fun things to do in Lake Geneva in winter, you might just want to come back every year.

Book the best tours in Lake Geneva

2. Green Bay

things to do near Milwaukee in winter, aerial view of green bay Wisconsin at sunset with many buildings and streets covered in light dusting of snow

Located a little over 100 miles from Milwaukee city center, Green Bay is also a suitable destination for winter retreats in Wisconsin.

If you’re into American football, the city is home to Green Bay Packers so you can enjoy the sports atmosphere while cheering on the home team during your weekend trips in Wisconsin.

Green Bay is also a great spot for winter getaways in Wisconsin, as you can find some of the best winter resorts in the area that offer fun indoor and outdoor things to do near Milwaukee in winter.

Are you into outdoor activities like cross-country skiing or sledding? Or do you prefer pampering yourself with a spa getaway at some of the best winter resorts in Wisconsin?

Green Bay is a place to be! You’ll love all the amazing things to do in Green Bay.

Book the best tours in Green Bay

3. Wisconsin Dells

best road trips from Milwaukee in winter, Mt. Olympus Resort with ancient greek-looking pillars and roller coaster

If you’re looking for winter trips with kids from Milwaukee, there is no better choice than Wisconsin Dells to guarantee fun Wisconsin road trips!

Known as the “Waterpark Capital of the World,” Wisconsin Dells is home to over 20 waterparks around the city that offer various winter getaway ideas from Milwaukee.

You can find some family-friendly indoor waterparks like Meadowbrook Resort or Yogi Bear Camp-Resort.

If you prefer the outdoors, why not try winter ziplining to make the best day trips from Milwaukee in winter?

This is undoubtedly one of the best things to do in Wisconsin Dells in winter and will make your visit unforgettable.

Book the best tours in Wisconsin Dells

4. Kewaskum

Milwaukee day trips in winter, two snow tubes up close on snow with snow-covered hill and several people tubing in background

Kewaskum is a small village only 30 minutes from Milwaukee, making it one of the best alternative destinations for day trips in Wisconsin if you want to escape the big city vibes.

Home to Sunburst Winter Sports Park, the park is best known for its tubing hill.

The village draws thousands of visitors from the Midwest area every year, in addition to being known as one of the best destinations that offer family-friendly things to do in Wisconsin in winter.

Buy the ultimate Wisconsin road trip itinerary

5. Cedarburg

best excursions from Milwaukee, wooden bridge over a river in Cedarburg, WI with green grass and trees beyond under a bright cloudy sky

One of the cheap getaways from Milwaukee in winter, Cedarburg also offers many activities to explore around the city.

Visiting Wisconsin isn’t complete without trying the local beer. Hop over to The Fermentorium, where you can enjoy top-notch Wisconsin beers with high-quality ingredients.

Whether you like IPAs or fruit beers, it’s the best place to go for winter road trips from Milwaukee!

Stay overnight at the best Cedarburg vacation rentals

6. Eagle

winter road trips from Milwaukee, Beautiful hillside of the Kettle Moraine State Forest in Wisconsin with red flowers and tall green brush stretching out into an area of green trees all under a vibrant blue sky with some wispy white clouds
Kettle Moraine State Forest in Wisconsin.

Situated in the beautiful scenic view of Kettle Moraine State Forest in the southeast of Milwaukee, you can reach Eagle, WI, by a short drive from Milwaukee downtown.

During the warmer season, it’s home to one of the best biking trails in Wisconsin. In winter, it’s also a haven for various outdoor activities, from snowshoeing to skiing.

The small town is also home to Old World Wisconsin, where you can explore one of the largest living history museums in the United States.

Although the museum stops its operation during winter, it regularly hosts special occasions that you can participate in when visiting Eagle during the holidays.

Visiting Eagle and booking their “Home for the Holidays” event are some of the most recommended things to do around Milwaukee in winter.

Here you can experience the 19th-century holiday celebrations in the Midwest as if you live in the late 1800s!

Book the perfect car rental for your trip

7. Kenosha

winter getaway ideas from Milwaukee, View of the front of the Mars Cheese Castle with two large signs and various flags on poles with a parking lot out front under a cloudy blue sky
Photo by Bart Everson on Flickr

Located only around 40 miles from Milwaukee, Kenosha is one of the easiest day trips from Milwaukee in winter.

Nestled between Milwaukee and Chicago, Kenosha is one of the best places to visit in Wisconsin in winter from people in both cities.

Kenosha is probably best known for its famous Mars Cheese Castle, but there is so much more you can do in winter day trips from Milwaukee if you visit the city.

In addition to sampling some of the best Wisconsin cheese and beers in Kenosha, the city also offers various outdoor activities for thrill-seekers.

Home to one of the best snowmobile trails in Wisconsin, you can enjoy the 200 miles of trails within the county if you’re feeling outdoorsy!

Additionally, for a fun winter trip, Kenosha also has one of the top ski resorts in Wisconsin, Wilmot Mountain.

Stay overnight at the best Kenosha cabin rentals

8. Chicago

winter getaways from Milwaukee, Wide view of the Chicago Bean sitting in an open outdoor square covered in a light layer of recent rain with tall skyscrapers behind under a dark cloudy sky at night

If you’re more into big cities, Chicago is definitely one of the best day trips from Milwaukee in winter. It’s also one of the best Midwest weekend getaways if you’re able to stay longer.

As the largest city in Illinois and the third most populous city in the United States, Chicago has so much more to offer all year round.

For around a 2-hour drive, you can reach the windy city from Milwaukee easily.

Don’t miss the chance to go ice skating at the iconic Millenium Park, as you can have a fun day out with your loved ones while enjoying the backdrop of the city’s skyline around Michigan Avenue.

You can also escape winter and head to the Lincoln Park or Garfield Park Conservatory to warm up inside the city’s indoor botanic gardens.

While strolling around the gardens, take some time to familiarize yourself with various tropical flora to maximize your visit to the conservatories!

Book the perfect car rental for your trip

9. Racine

best day trips from Milwaukee in winter, Aerial shot of a lighthouse and its accompanying residential buildings surrounded by green grass and trees with the calm ocean beyond all under a vibrant evening sky with clouds

Snow and cold weather are inevitable when traveling to Wisconsin during winter, but it shouldn’t stop you from exploring outdoor activities to make the most of your stay.

Racine is another option for day trips from Milwaukee in winter, as you can book a guided inland ice fishing tour to catch some of the best Wisconsin fish, from panfish to Northern Pike.

You should also visit the Racine Lighthouse, one of the best lighthouses of Wisconsin and one of my favorite winter excursions from Milwaukee.

Buy the ultimate Wisconsin road trip itinerary

10. Madison

winter day trips from Milwaukee, View of Madison Capitol Building as seen at the end of a snow-covered street lined with bare winter trees under a bright cloudy sky

Another excellent destination for Milwaukee day trips in winter is Madison, the Wisconsin university town has so much to offer for all types of visitors.

Winter in Madison, WI is truly magical, and a must-visit this time of year. You don’t want to miss ice skating at the Edgewater Hotel.

Head to the University of Wisconsin-Madison’s Arboretum for a winter hike, one of the best things to do in Madison, WI.

This is some of the best hiking in Madison, and you can enjoy the natural landscape with the white snow in the surroundings.

Another popular activity in Madison is dining in a dome where you can indulge in the city’s culinary scene to enjoy the best of your winter holiday in Wisconsin.

Book the best tours in Madison, WI


Milwaukee is a great place to start your winter getaways in Wisconsin. There are a lot of winter activities near Milwaukee that you should add to your bucket list, and most of them can be done easily for day trips from Milwaukee!

Whether you’re in for traveling inter-state to Chicago or prefer short-drive destinations like Racine or Kewaskum, the options for day trips from Milwaukee in winter are endless!


FAQs About the Best Day Trips from Milwaukee in Winter

What do people do in the winter near Milwaukee?

There are a lot of things to do around Milwaukee in the winter, including fun road trip options. There are plenty of day trips from Milwaukee in winter where you can go hiking, enjoy winter festivals, try local food and beer, or just enjoy the local sites.

What are the best day trips from Milwaukee in winter?

It depends on what sort of day trip you are looking for. But some of the best options are Wisconsin Dells, Eagle, and Lake Geneva.

What are the best winter activities near Milwaukee?

Wisconsin has pretty much every winter activity imaginable. From Milwaukee and the surrounding area and cities, you can enjoy winter sports like snowshoeing, skiing, or ice skating. There is also winter hiking and camping. Or you can enjoy festivals, such as WinterFest in Lake Geneva.


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