Winter in Wisconsin: What to Expect at Wisconsin's Most Popular Ski Spots

It’s winter in the Midwest, and that means it’s time to take advantage of sunny 20- and 30-degree Saturdays and Sundays to hit the slopes. With two holiday winter weekends adding potential “bonus” ski days, there’s plenty of time between January and March to get outside and enjoy winter sports.

I learned to ski in the Midwest, and we are incredibly lucky to have the ski areas highlighted below so close to home. They give us the chance to get outside and experience one of my favorite winter sports. I have especially fond memories of family trips to Devil’s Head and Boyne between the ages of 10 and 15.

I’m deeply thankful to my parents for giving me the opportunity to learn how to ski during those years. Without those experiences, I’m fairly certain I never would have picked up the sport again in my mid-40s — this time alongside my son. That decision has led to countless family, friend, and father-son trips to Wisconsin, Michigan, and even Colorado. The gift my parents gave me continues to pay dividends.

Below, I’ve included an overview of five ski resorts in Wisconsin, along with a shout-out to one in Illinois.

Here’s to Midwest skiing.

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Devils Head is in close proximity to Cascade and offers a similar ski experience to Cascade. The big difference is that Devils Head is a full resort with lodging, a pool, restaurants and bars while Cascade is all about the skiing, though it does have a cool bar and basic ski cafeteria style food. Here's my overview of Devil's Head.

• 2 hours and 50 minutes from Chicago

• 30 runs, 6 lifts and some forested trails that are much longer than what you find at Wilmot, Chestnut or Alpine Valley. My favorite runs at Devil's Head that showcase the best of this mountains winding, forested terrain are Dante's Inferno and The Cauldron.

• Fun place for beginners, families and experienced skiers.

• This is a fun place for a 2 night trip and with Cascade nearby, you could easily ski 1 day at 1 location and visit the other for something slightly different.

• The resort is dated, but it also has a lot of rustic charm and has ski-in, ski-out options and quick and easy access to the lifts from the lodge. Everything is connected. If I was an and Epic or Icon board member, I'd suggest they look at buying this resort. It's a hidden gem.

• The view from the Devils's Den Bar and Grill inside the resort of night skiers taking in a jump, with snow machines blowing into the cold January weather to make snow, is terrific.

Terrific view of night skiers from the Devils's Den

Cascade is a terrific place to ski and its probably the best skiing your going to find in close proximity to Chicago. Check out my post below for an overview of Cascade.

• https://www.seeliveeat.com/post/ski-season-a-review-of-wisconsin-s-cascade

Granite Peak is a bit further from the Chicagoland area but the extra drive is worth it to take in one of the better on the slope experiences in the Midwest. Check out my post below for an overview of Granite Peak.

• https://www.seeliveeat.com/post/ski-season-wisconsin-s-granite-peak

Alpine Valley has much more than Wilmot including a full resort and lots of terrain parks. The runs aren't long but this is a fun place to ski with many amenities. Here's my overview.

• 1 Hour 45 minutes from Chicago

• Great for beginners of all ages and for children in lessons with 20 runs and seven lifts.

• Three decent terrain parks that are fun for skiers and snowboarders: no tubing hill.

• Much more enjoyable for families and experienced skiers than Wilmot. The runs are longer, with more turns and the hill is much larger. Alpine has a great ski resort feel to it that isn't easy to replicate.

• The amenities and food are decent and they have a full resort with lodging and restaurants. There are music concerts in the summer and this is a fantastic place to see a concert (I will never forget seeing Radiohead here in 2003).

  
  

Wilmot is a really nice spot with all that Colorado (Vail owns them) money but its very much a spot to learn and isn't much fun for experienced skiers. Here's my overview of Wilmot.

• 1 hour and 15 minutes from Chicago

• 25 runs, 7 lifts and 4 progressive terrain parks. Wilmot has plenty of lessons for all ages available and is a great place to learn to ski and get comfortable on the slopes before moving onto something more challenging.

• They have a terrific tubing hill and nice amenities with a cool bar and restaurant.

• They did a great job on their terrain parks which are very popular with the teenage crowd.

  
  

I'm going to end this post with a shout out to the one place I've skied in Illinois. It offers something unique since you get to ski down from the lifts towards the amazing Mississippi River. Take a peak at Chestnut Mountain.

• 2 hours and 40 minutes from Chicago

• 19 runs, 6 lifts and plenty of opportunities for lessons

• They have a resort with lodging, restaurants and bars. It's a charming and unique spot that is perfect for a couple days (and nights). Located near Galena and its rolling hills, Chestnut Mountain in located in one of the most beautiful parts of Illinois near the Iowa border and the Mississippi River.