Wisconsin's Gangster Tour: 2 Thrilling Itineraries
Wisconsin is famous for many things, but did you know it was a popular gangster hideout in the 1920s and 30s? With its lush forests and picturesque small towns, the state attracted Chicago-based gangsters like Al Capone and John Dillinger on the run during the prohibition era. Today, you can stop in at supper clubs with bullet holes still in the walls and visit locations where Hollywood has recreated famous heists.
If you’re looking for a getaway with a side of secret history, look no further. Go “On the lam” in Wisconsin and experience the rich lore and legend of Wisconsin's past. These itineraries will guide you through some of Wisconsin's most notorious locations in history and on the big screen—and suggest some bonus stops along the way.
Stop in at these Wisconsin destinations with real gangster history.
Norwood Pines Supper Club - Minocqua
A popular gangster dinner spot in the 1920s and 30s, Norwood Pines still operates as a restaurant surrounded by stately red pines, views of Patricia Lake and grazing whitetail deer. Dine on their screened-in porch or stay cozy by the fireplace and feel the history around you in one of Northern Wisconsin’s oldest supper clubs.
Legacy Lodge - Hayward
In 1929, Chicago gang leader, beer baron and speakeasy operator, “Polack Joe” Saltis built this 238-acre estate on Barker Lake near the town of Winter, not far from Al Capone's own hideout estate. Today, visitors can stay in the historic lodge, rent one of the cabins on a weekly basis and play golf at the Barker Lake Golf Course.
The Landing - Hayward
According to wiseguy legend, in 1949 Joey “The Doves” Aiuppa caught a world-record muskie at The Landing. On the run from the law, Aiuppa sold the 69-pound, 11-ounce fish to Louis Spray. Spray, a former bootlegger himself, registered the catch as his own and has been recognized as the world record holder ever since. Stop in at the resort restaurant to try the fish fry for yourself, though these days their specialty is local Chippewa Flowage Walleye.
Silver Street Distric - Hurley
Hurley's Silver Street district was popular among “vacationing” gangsters and remains full of lively taverns, although today the area is better known for its beautiful waterfalls and expansive ATV trails.
Little Bohemia Lodge - Manitowish Waters
The site of a 1934 shootout between the Dillinger gang and FBI, the Little Bohemia Lodge still operates as a restaurant and was used as an authentic filming location for the movie Public Enemies' recreation of that fateful night. The property has been faithfully preserved to maintain its unique history: original bullet holes still pepper the walls, Dillinger memorabilia is on display and rumors of a missing bag of money lost in the shuffle of the gang's escape still remain. Stop by for some short ribs and for a chance to find some gangster gold.
Dillman's Bay Resort - Lac du Flambeau
Cabin 5 at this modern-day resort was used by Baby Face Nelson as a hideout following his escape from the FBI shootout at the Little Bohemia Lodge. These days, the property on White Sand Lake is available for vacation rentals and events and even hosts art workshop retreats.
On the Big Screen: Filming Locations
In 2008, Hollywood came to Wisconsin to film the big-budget mob movie Public Enemies. Explore a few now-famous locations throughout the state.
Lafayette County Courthouse - Darlington
Johnny Depp stood trial in Public Enemies in handcuffs and leg shackles at the Lafayette County Courthouse, which substituted for the courthouse in Crown Point, Indiana where Dillinger was arraigned after being captured. Stay in an old-timey mood by strolling through Darlington's historic downtown past shops, restaurants and the Driver Opera House and feel like the star of your own movie.
For Public Enemies, downtown Columbus was converted into Greencastle, Indiana, circa 1933: the site of a $75,000 robbery by Dillinger and his gang with the West James Gallery made into the Central National Bank. Take a free tour of the Farmers and Merchants Union “Jewel Box” Bank, a national historic landmark designed by architect Louis Sullivan. After, pick up some historical treasures of your own at Wisconsin’s largest antique mall.
Public Enemies served as a homecoming for director Michael Mann, who attended the University of Wisconsin-Madison. The crew shot at several Madison locations, including in and around the Wisconsin State Capitol Building, which doubled as the FBI headquarters for the film. To learn about the capitol square’s real history, schedule a walking tour and blast into the past.
Milwaukee County Historical Society Building - Milwaukee
During the mafia's heyday, Milwaukee was home to some of the organization's most powerful men, including Frank Balistrieri, who was considered for head of the Commission, the mafia's governing body. Several Public Enemies scenes were filmed in Milwaukee, including a bank robbery scene at the Milwaukee County Historical Society Building. To learn more about the city's more sinister history, try a gothic tour.
EAA Aviation Museum - Oshkosh
To see a replica 1920s aircraft that was featured in Public Enemies, stop in at the EAA Aviation Museum where it’s still displayed. EAA’s Pioneer Field was also the filming location for the scene in which John Dillinger makes his appearance at the Midway airport in Chicago.
While you’re there, take a ride in a vintage airplane at Pioneer Airport—a real working aerodrome right out of the “golden age” of aviation. Then, visit a piece of history in the Eagle Hangar, a tribute to World War II aviation. Bring the kids along and stop in the KidVenture interactive gallery for extra fun.
Looking for more historical fun? Keep partying like it's 1920 with these Wisconsin speakeasies.