Top 10 Winter Things to Do in Waukesha and Milwaukee County
Top 10 Winter Things to Do in Waukesha and Milwaukee County
Winter in Wisconsin is anything but boring. When the snow begins to fall and the lakes freeze over, Pewaukee and the surrounding Lake Country region transform into a winter playground filled with outdoor adventures, cozy dining experiences, family attractions, and seasonal activities. Conveniently located in the heart of Lake Country and just minutes from Milwaukee, The Ingleside Hotel is the perfect home base for a winter getaway.
Whether you're planning a family vacation, couples retreat, weekend staycation, or holiday escape, here are the top things to do near The Ingleside Hotel during the winter months.
1. Make a Splash at Springs Water Park
Winter weather doesn't stop the fun at Springs Water Park, located right inside The Ingleside Hotel. This 45,000-square-foot indoor water park offers a warm escape from the cold with thrilling water slides, a lazy river, activity pools, and interactive play features for all ages. Families love that they can enjoy a true vacation experience without worrying about snow, ice, or freezing temperatures. The park provides year-round entertainment and is one of the most popular indoor attractions in southeastern Wisconsin.
Perfect for: Families, staycations, school breaks, and weekend getaways.
2. Explore Pewaukee Lake's Winter Beauty
While summer draws crowds to Pewaukee Lake, winter offers a completely different kind of charm. Bundle up and take a scenic stroll along the lakefront to enjoy peaceful views, snow-covered shorelines, and beautiful winter sunsets. The downtown Pewaukee waterfront creates the perfect backdrop for photos and a relaxing afternoon outdoors.
Perfect for: Couples, photographers, and anyone looking to enjoy Wisconsin's winter scenery.
3. Go Cross-Country Skiing or Snowshoeing
Winter outdoor enthusiasts will find plenty of opportunities nearby. Waukesha County Parks maintains groomed cross-country ski trails at Menomonee Park and Minooka Park, offering miles of scenic trails through forests and rolling terrain. Snowshoeing is also popular throughout the park system, with trails suitable for beginners and experienced adventurers alike.
Nearby favorites include:
• Menomonee Park
• Minooka Park
• Retzer Nature Center
• Fox River Park
Perfect for: Outdoor explorers, active travelers, and nature lovers.
4. Enjoy Wisconsin's Favorite Winter Tradition: Sledding
Nothing says winter fun quite like sledding. Several parks throughout Waukesha County offer designated sledding hills when conditions allow. Families can spend hours racing down snowy hills and enjoying classic winter memories together. Menomonee Park, Minooka Park, and Lowell Park are popular local choices.
Perfect for: Families with children and visitors looking for classic winter fun.
5. Experience Country Christmas
If you're visiting during the holiday season, don't miss Country Christmas, one of Wisconsin's largest drive-through holiday light displays. Featuring millions of twinkling lights, animated displays, and festive holiday scenes, this annual tradition has become a must-see attraction for families across the Midwest. The event is located right on the grounds of The Ingleside Hotel, making it incredibly convenient for overnight guests.
Perfect for: Families, couples, and holiday travelers.

6. Discover Winter Fun in Milwaukee
Just 20 to 25 minutes from The Ingleside Hotel, Milwaukee offers numerous indoor attractions ideal for colder days. Spend the afternoon exploring museums or enjoying shopping and dining in the Historic Third Ward.
Must-see attractions include:
7. Hit the Ice
Ice skating remains one of Wisconsin's favorite winter activities. Visitors can enjoy indoor skating at nearby arenas such as Naga-Waukee Ice Arena and Eble Park Ice Arena. Whether you're practicing your skills or introducing the kids to skating for the first time, it's a fun way to embrace the season.
Perfect for: Families, date nights, and winter sports enthusiasts.
8. Experience a Milwaukee Bucks Game
Winter is sports season in Wisconsin, and few experiences are as exciting as cheering on the Milwaukee Bucks at Fiserv Forum.
Basketball fans can enjoy:
• NBA action
• Dining and entertainment in the Deer District
• Special events throughout the season
You can also catch a Milwaukee Admirals hockey game or Milwaukee Wave indoor soccer match for even more sporting excitement.
Perfect for: Sports fans, groups, families, and visitors looking to experience the excitement of Milwaukee's professional sports scene.
9. Catch a Concert, Comedy Show, or Broadway Performance
Milwaukee and Waukesha County entertainment calendar stays busy throughout the winter months, offering visitors countless opportunities to enjoy a night out. From nationally touring Broadway productions and headline concerts to comedy acts and symphony performances, there's always something happening in the city.
Popular venues include:
• Marcus Performing Arts Center
• Miller High Life Theatre
• Riverside Theater
• Pabst Theater
• Fiserv Forum
• Waukesha Civic Theater
• Milwaukee Improv
Perfect for: Couples, friend groups, theater lovers, and music fans.
10. Shop, Dine, and Discover at The Corners of Brookfield
For a fun indoor winter outing, head to The Corners of Brookfield, one of southeastern Wisconsin's premier shopping and entertainment destinations. This open-air lifestyle center offers something for everyone, making it a great way to spend a chilly Wisconsin afternoon.
Enjoy:
• Boutique and national retailers
• Unique local shops and specialty stores
• Restaurants and casual dining options
• Coffee shops perfect for warming up on a winter day
• Seasonal events and holiday activities
Perfect for: Shoppers, couples, friends on a getaway, holiday shoppers, and foodies.

Plan Your Winter Escape at The Ingleside Hotel
Winter is one of the most underrated times to visit Pewaukee and Wisconsin's beautiful Lake Country region. From snow-covered trails and holiday lights to indoor water park adventures and live sports, there's something for everyone to enjoy. Whether you're traveling with family, planning a romantic weekend, or simply looking for a change of scenery, The Ingleside Hotel offers the perfect combination of comfort, convenience, and winter fun.
Book your winter getaway today and discover why Lake Country is the perfect destination all season long.