Our Story

Freedom Island History

Once compared to Sodom and Gomorrah, legend says Trenton Island was the carousing grounds for notorious characters Jesse James, John Dillinger, and Pretty Boy Floyd, and was a general den of sin for gunslingers, bootleggers, and prostitutes. This little island boasts history equivalent to such greats as the Black Hills and Fort Sumner. In the late 1800’s Red Wing would run a ferry twice a day over to Trenton Island in order to access Wisconsin.  

During this time the only thing on Trenton Island was a primitive road that would flood in high water. This all changed in 1895 when the high bridge connecting Minnesota to Wisconsin was opened on May 1st. Both Red Wing and Pierce County residents were engaged in quite the celebration.

But by 1908, all the warm and cozy feelings that Red Wing residents had about Trenton Island had truly dissipated.

Shortly after a raid shut down the booze dens and brothels of Trenton Island and put five women and seven men in jail. It was so bad that the Republican Eagle 1908 article even states: “Profanity and rank obscenity together with bestiality are the trinity on the Island Saturday nights.”

The article, probably one of the most slanderous pieces of literature ever written about the Island, goes on to state: “Sodom and Gomorrah in their palmist days of licentiousness would have to look to their laurels were they to be compared with the island over which sounds the peals of Red Wing’s church bells, and yet Heaven has not sent fire to destroy it nor has the public conscience of Red Wing risen in its might and smitten it, nor has Pierce county felt much uneasiness about this festering ulcer on her body.”

The second article was published in 1976, but provides a more detailed history of what occurred due to the 1908 raid of the Island. A year after the raid, the owner of most of the Island, May Cook, attempted to reopen her tavern, unfortunately the city of Red Wing had different ideas and were dead set on seizing her land and turning it over to Red Wing Public Works for the creation of public parks. And in more physical terms, a gang of men led by the Pierce County Sheriff confronted Mrs. Cook and literally tore down her buildings.

But that wasn’t the end of it. The most important repercussion from the raid of 1908 was prohibition on the Island as no more liquor licenses were to be granted. “Trenton has gone dry.” The account pointed out. “At the election held yesterday, license was buried under an avalanche of good men’s votes.”

As Trenton was often the local watering hole and liquor den for the people of Red Wing and supporting areas, the lost of the island, although, probably proper caused those interested in liquor to be out of a domicile.

The licentiousness of the Island proved to be international as the third article, which again recaps the raid of 1908 and the liquor interests on both sides of the river, originally, comes from a 1914 publication entitled “Tidsskrist” and was almost entirely written in Norwegian.

The dry Island, of course, did not stay dry for long, especially when Minnesota, along with the rest of the United States, established prohibition on January 16, 1920. There was endless trouble with the dry law violators. Some were fined, others committed to jail, but as fast as one crop was disposed of another appeared. Over the thirteen years of prohibition, actually fewer in Wisconsin which put the kibosh on prohibition in 1929, the Island became the new hotbed of illegal liquor production. During prohibition reduced strength beer, “near beer”, was still being served in a few places, although basically worthless as booze, it was a great base for cooking up a good moonshine, which just happened to be quite a stinky process. Where better to brew the smelly moonshine than on the sparsely inhabited Island, because you could definitely not brew stinky beer in Red Wing, where your priestly neighbor would sniff you out in a heartbeat!

Once prohibition was repealed across the United States in 1933, Trenton Island dropped out of the spotlight for a while. But that doesn’t mean that the same debaucherous activities were not going on here. The Island was still filled with divey dens of iniquity and go-go dancers lined every bar. Finally in the seventies the Island again got the spotlight but this time for the dancers.

Red Wing citizens were not too pleased with the article, but do not seem to make a point to weather they are upset with the content or the style with which it was written. Or perhaps they just wanted another venue to preach Jesus’ love, nevertheless, there were a handful of letters to the editor after that front page article.

Even into the beginning of the eighties of the island, part of Trenton Township held half dozen bars and eating establishments which was the residence of ta lot of trouble.
With the Pierce County HMGP project buyout of most of the Trenton Island properties (including the beloved Gene’s Bait and Tackle), the Island’s watering holes and go-go clubs have been limited. The Island is now home to two campgrounds, three marinas, and two restaurants/bars. Although no longer is the Island a hotbed for illegal activity, its infamy will still live on in the stories of gun fights, dodging prohibition, and all the rest of the immoral activities that the Island used to be residence to.