http://agency.travelwisconsin.com/images/Trailer%20Boat%20article.pdf

GANGSTERS IN THE NORTHWOODS
The Prohibition Era brought a new surge of visitors to Wisconsin’s Northwoods, including some who were escaping more just a regular workday. Aided by the newfound freedom of auto travel, Chicago gangsters routinely sought refuge in hideaways from Eagle River to Rice Lake. In some cases, these visits were all business - running liquor and/or setting up local prostitution and gambling operations - while in other cases they were “cooling off” periods after high-profile robberies in other states.

While the gangsters are long gone, their lore lives on... as do some of their hideaways. Little Bohemia Resort, for instance, was the site of an infamous 1934 shoot-out between FBI agents and John Dillinger’s gang (which included Baby
Face Nelson). After a bungled capture attempt, the gang escaped into the woods of western Vilas County. Dillinger himself supposedly hid for several days in the nearby Lac du Flambeau Indian Reservation, and reportedly buried a suitcase filled with $200,000 somewhere in the area. Some have speculated it was hidden along the shores of the Eagle River near Land O’Lakes... but it has never been recovered.

The Eagle River area itself was the site of an intense FBI investigation in the mid-1970s, when Teamster’s Union leader Jimmy Hoffa disappeared. Hoffa reportedly spent quite a bit of time at a Teamsters retreat there called the Jack O’Lantern Lodge. Though the surrounding area was searched thoroughly, no trace was ever found.

http://www.trailerboats.com/output.cfm?ID=1142209

The Capone Connection
The Northwoods of upper Wisconsin was a favorite getaway spot for Prohibition-era mobsters, who found all the seclusion they wanted in this labyrinth of forest and water. Many gangs built safe houses, the most famous being The Hideout — Al Capone’s heavily fortified summer cottage near Couderay (about a two-hour drive west of Eagle River). Now a tourist attraction, the 400-acre estate has been kept much the way it was when Capone was there in 1925. Notable architectural details include 18-inch-thick walls and machine gun turrets in the cabin. There was even an airstrip where planes from Canada would land and drop off alcohol that the gangsters could run to Chicago.

Other Northwoods towns rumored to have had mob connections include: Mercer, in Iron County, where Al Capone’s brother Ralph ran a resort after serving jail time; Rhinelander, in Oneida County, where Sam Giancana supposedly vacationed; and Elcho, in Langlade County, which was rumored to have had a medical station for gangsters escaping to and from Wisconsin.

http://www.dnr.wi.gov/org/water/fhp/lakes/selfhelp/lkmnews/v12n1a.htm
Everett's Resort, located five miles west of Catfish Lake, dates back to 1885. Tourism began to boom in the 1920's. The most notorious resort, The Jack-O-Lantern, opened in 1931. It came on the heels of the "roaring twenties' during which time lavish summer homes and resorts sprang up throughout the area.

http://72.14.209.104/search?q=cache:GYvfr7KLyRIJ:www.lakelandtimes.com/features.php%3Fstory%3D103+%22Jack+O%27Lantern%22+%22eagle+river%22&hl=en&gl=us&ct=clnk&cd=35

Audrey Voss Dickerson By: Joyce Laabs Published: July 15, 2005

Editor’s Note: As Audrey Voss Dickerson prepares to mark her 94th birthday Aug. 12, we spent an afternoon visiting with at Voss’ Birchwood Lodge in Manitowish Waters – and to update a feature we wrote on her in the 1970s. We thought her remarkable then – and think her remarkable today.

“Sometimes I would put on my black suede pumps and Bob and I would get in our model A and head for the Jack O’ Lantern Resort in Eagle River. We would gamble and play the slots. Eventually, the slots were declared illegal and federal agents came in and wrecked them all.”