Whitecap Ski Resort A Retro Midwest Ski Mecca

Feb 7

Forgotten and falling apart.

Is how the outside world sees Whitecap Ski Resort in Upson, Wisconsin.

Filed for Chapter 11 bankruptcy in November 2025, only with plans to stay open for the 25-26 season while they reorganize their debt, and now they're selling season passes for the 26-27 season?

After skiing this "bare bones," borderline unsafe resort, I did a little digging to see why this place looks straight out of the 70's. And what I found, thanks to some simple internet sleuthing, is that it looks like the 70's because it is and few upgrades have been made since.

Is this resort a forgotten gem in the Midwest?

No, not by a long shot. Maybe a gem, but not forgotten. This ski area has been around long enough to earn its way right into Midwestern ski history.

It feels like everyone's grandparents who skied in the "Good Ole Days" before greed and Vail entered the chat, has a story about a legendary powder day at Whitecap Resort and its traumatizing up and over lift. Plus, the walls of the on-piste wine hut hold enough history to keep you entertained for days.

Because of how far north this resort is, they see the same amount of snow as Western U.P. resorts, averaging 3-4 times the snowfall of most Midwest resorts.

Unfortunately, recent years' weather has been unkind to the winter sports area. Paired with its 400 skiable acres, 3 summits, and 48 runs, this resort could position itself as a Midwest mecca.

However, locals, skiers, and snowboarders alike have all expressed concern about the actual operational safety of this rickety resort.

With some of the best and most vast terrain in the Midwest, it's truly heartbreaking to see it falling apart, getting poor reviews, and ultimately struggling to keep up with competitors who have three times the funding. Despite their issues, they keep the chairs spinning.

At least for now.

So what makes this retro resort so rustic?

One double chair lift installed during the original construction has a legend of its own.

While edging on the unsafe side, and affectionately known as the "Ole Gap" Chair, now rebranded as the "North Pole/South Pole" Chair, it happens to be easily the scariest lift I have ever seen in operation.

Topping off at a whopping 125 ft tall, towering over the Midwestern treeline, at one point in time people would ride this lift peak to peak. Did I mention it has NO safety bar?

While riders can no longer take the lift all the way across the "gap," according to The Lift Blog, this was still the case until the 19-20 season, when the resort found new owners and their ski patrol staff joined the NSP and deemed it unsafe. Not the whole lift. Just the peak to peak part.

Despite all of this, the terrain for skiers and snowboarders is unmatched as far as Midwestern standards go. They have long open groomers, winding tight runs, fun cliff drops, and perfectly packed gladed runs.

This also isn't a resort I would bring my beginner friends or small children to. There aren't a lot of green runs, and there are no great beginner learning areas.

They have a magic carpet, but it never seems to be running and it's maybe 20 feet long. Most people can walk the green pitch faster than the surface lift can move.

The Come back Resort?

As I'm reading this back, I realize I don't have a ton of positive things to say about this place and that's truly unfortunate, because it was a great place to ski.

The lack of upkeep and upgrades makes it hard to enjoy when just a little farther north, your biggest competitors, Midwest Family Resorts, are becoming the next Vail and seem to have endless funding for the latest and greatest.

I sincerely hope this resort can find new ways to rake in revenue and keep the chairs, hopefully new ones soon, spinning.