Four Family Friendly Winter Resorts and Skiing Destinations in Wisconsin

Dec 16, 2023

We’re gearing up for holiday break and winter vacations with a fun vacation planning blog! Hop in your new car from Classic and let’s hit the road to fun in the sun and snow as we travel across Wisconsin at these amazing resorts and ski-slopes. Plus, if you’re looking for a great “gift of experience” instead of something bought in a store, this is a great source of inspiration for last minute gift ideas with lasting memories! Gift your loved ones a “vacation coupon” to one of these amazing winter sports and snow filled destinations.

Let’s check out Alpine Valley Resort in Elkhorn.

This year-round resort offers 365 days of fun, but you’ll find peak excitement in winter weather months! Located just 2 hours from Chicago, this incredible family friendly resort is located in Southeastern Wisconsin. The best time to visit is December through February for peak winter sports action, but the ski slopes are open from November through March, weather permitting.. There are 21 runs in total, snowmaking capabilities, and beginner to advanced options. If you’re new to skiing and snowboarding, you can take advantage of their copious amounts of lessons including children’s lessons, build-your-own private lesson bundles, adult group lessons, and Ski School. Lodging options are plentiful with over 100 rooms to choose from, but please be aware that certain time periods have a 2 night stay minimum. Warm up after some fun in the snow with the indoor heated pool and hot tub.

Next up is Cascade Mountain in Portage. Make sure to purchase your tickets in advance for this family friendly skiing and snowboarding destination, because it is hot hot hot when it comes to winter travel. With 48 different trails to choose from, folks of all ages and experiences levels will find something new to try! There’s even snow-tubing for those who prefer something with plenty of excitement but a little less daring. The area has a wonderful natural snowfall accumulation, but also has state of the art snowmaking capabilities for a perfect ride all season long. There’s instructions and lessons on site for all experience levels, whether you’re a first-timer or you’re looking for a little more of a competitive edge with some racing and intense sport action. Lodging options are just a short drive away and include Cedar Lodge and Settlement, Natura Treescape Resort, Atlantis Family Waterpark Resort, and Great Wolf Lodge.

We can’t forget the family favorite Grand Geneva Resort & Spa in Lake Geneva! In December, the resort leans full force into the holiday spirit! The 12 days of Christmas event includes outdoor holiday lights and a drive-through light show, along with breakfast with Santa, and trolley tours! There are 20 different runs on the mountain, along with fun options such as cross country skiing, sledding, snow shoeing, and ice skating. You can book a room at the Grand Geneva and Timber Ridge Lodge, and dine at the finest restaurants such as Leinenkugel’s Mountain Top Lodge. Plus, the fun doesn’t end when the sun goes down! Enjoy an amazing session of Night Skiing for a special experience. Lessons are offered on your winter sport of choice, for all ages and skill levels. The resort also offers memorable weekly experiences and special events throughout the season.

One of the oldest resorts in the Midwest with oodles of winter fun is Little Switzerland in Slinger. Skiing and Snowboard enthusiasts will love this classic destination with 18 different trails, the longest run of which is 1800ft! No equipment? No problem! Book a package and opt for equipment rentals, perfect for kids who want to test the waters and take a few lessons. They offer an expansive selection of lessons for beginners, so it’s perfect for families. Plus, with state of the art snowmaking, they’ve got plenty of challenging runs to keep intermediate and advanced skiers and snowboarders too. Need a place to stay? They’ve got you covered with these wonderful properties owned and operated by the folks at Little Switzerland; you can stay at The Apres House or The Founders’ House. Other hotels nearby include the Washington House Inn, Cobblestone Hotel and Suites Hartford, Hampton Inn & Suites West Bend, and more.