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Dennis McCann


Pembine: Second life for Four Seasons Island Resort generates quite a buzz as part of massive Pine Mountain Ski & GR facelift

  • 3 min to read

A state line resort that boasts a golf course with multiple five star ratings will get a much needed facelift, thanks to a new ownership group, while a nearby shuttered resort with a modest nine-hole layout that has gone back to nature will be reborn.

So guess which development is getting the most positive response?

“It’s very unique,” said David Nyquist, who is handling marketing for the new Ohio-based owners, Lakeshore Management LLC. “People are excited about TimberStone and Pine Mountain, but they’re very excited about the Four Seasons.”

About those properties: Pine Mountain Ski and Golf Resort, which includes TimberStone GC, is near Iron Mountain, on the Wisconsin-Michigan border. Four Seasons Island Resort is near Pembine in far northeastern Wisconsin, situated on little Miscauno Island in the middle of the Menominee River. The resorts, about 30 miles apart, are less than 1.5 hours from Green Bay.

Nyquist said the new owners were initially interested in Four Seasons, which had been closed for several years despite the infusion of millions of dollars in upgrades when controlled by earlier owners. It was only after a real estate agent pointed out the potential at Pine Mountain that the owners decided on taking over both properties, intending to operate them together.

First, however, there will be millions of dollars spent on upgrades at Pine Mountain, where Nyquist said the lodging was not up to the quality of the golf course, and to get Four Seasons ready to reopen after its long closed-door nap. While the lodge itself won’t require major changes, after two years without maintenance the golf course will need a total rebuild.

“As you can imagine,” Nyquist said, “after two years it went completely native.”

When improvements are completed, the result will be lodging at both resorts, 27 holes of golf, meeting and wedding facilities, downhill skiing, snowboarding, snowmobiling, dining and more. In a statement, Michael Cameron, who will serve as general manager for both properties, said the ownership was “fully committed to working diligently to make much needed improvements while respecting the long and amazing history of these two incredible resorts.”

The history at Four Seasons, especially, is a major reason for the excitement over its reopening. The resort was built on a scenic stretch of the Menominee River in 1905 to serve visitors who arrived by railroad, mostly from Chicago and most with enough time and resources to spend much of their summers in northern Wisconsin. Amenities included golf, horse stables, a pool, tennis courts and, of course, nightlife so jumping that even Prohibition couldn’t stop the fun. A five-piece orchestra would play on Saturday nights, and there were table games for the willing.

“These were the best people you could find in society,” former owner Walter Ross told the Milwaukee Journal Sentinel in an interview in 2002.

Rumors often suggested not all customers were the best society could offer, but despite repeated stories that mobster Al Capone was among the Four Seasons’ guests Ross and his wife, Marie, were adamant that “Scarface” had never visited the property. “Don’t ever say anything about Al Capone coming here,” Marie Ross said in that same interview. “He never was in our place. Ever, ever, ever.”

There was no debate about whether a later group of owners fit Ross’ description as the best society could offer. In the late 1990s a group from Cicero, Illinois, bought the resort and poured millions of dollars into improvements to make it truly a luxury resort on the little island. Only the finest fixtures and furnishings were good enough, but when they were done Four Seasons was hopping again, hosting weddings, events, snowmobilers and golfers in the lavishly resort resort.

If such free spending at a tiny island resort puzzled Four Seasons’ neighbors, it was a little easier to understand when federal officials swooped in, accusing the Cicero group of siphoning about $12 million from the city’s health insurance fund during the 1990s. About $5 million had been put into the resort during their ownership.

Nyquist said the new owners will certainly benefit from the spending of the previous group, however the funds were obtained. And he said the resort’s lodging and other facilities will be able to open without a great deal of effort. On his first walk-through, he said, it appeared as if the hotel had closed in the fall expecting to re-open soon.

“It’s almost shocking,” he said. “It’s almost like a ghost ship. It almost looks like you could check right in. The property is in phenomenal condition.”

Nyquist said the bar at Four Seasons will open this fall, while lodging will be available in late 2018 or early 2019 in time for snowmobile season. Renovations at Pine Mountain are underway, including improvements to all guest rooms, common areas, wedding and meeting facilities, decks and lodge façade.

When the golf course is again ready, Nyquist foresees a shuttle bus so guests at each resort can play the golf course at the other, even 27 holes in a day.

And marketing efforts are also underway, including a nod to the Four Seasons’ reputed past, however much the Rosses protested. Nyquist said there are enough references to unsavory guests through the years to play that up in promoting the resort because gangster history plays well.

“I’ve been told by many, many people that if (Capone) didn’t stay here other gangsters (did). Senior motor coaches will absolutely love that.”


A Wisconsin native & longtime newspaperman, Dennis has been writing about golf for more than 20 years. When not profiling golf's colorful characters or the courses they play, he can usually be found golfing at beautiful Apostle Highlands GC in Bayfield.