Chicago gangsters during Prohibition used Wisconsin as a getaway for kicking back and doing business in quiet, secluded settings. Al Capone even built a big fieldstone house with armed-guard watch towers and an airstrip on 400 acres in the Northwoods, near Couderay, perfect for transporting illegal hootch, storing ammo and hiding out with partners in crime.
When they wanted a night out, they patronized rural supper clubs. Some gained notoriety because of gangster talk, real or fabricated. Experience the mysteries and stories that these 5 supper clubs hold.
Take a window seat on the enclosed, slanted porch that faces the Rock River. During Prohibition, the supper club’s owner doubled as a bootlegger whose moonshine routinely was shipped downstream. Add slot machines, reportedly from the Mafia, and gangsters as customers, including Al Capone’s buddies.
From the outside, this century-old building resembles a tattered dive bar. Inside, it’s homespun, cozy and quirky, with serious farm-to-table cooking by owners who double as farmers.
Sandwiched between a sports bar and office building is a cozy, brick and house-like structure with deep gangster roots. When the brother of Chicago mobster Roger “The Terrible” Touhy opened Wonder Bar in 1929, he was expanding the family business – illegal alcohol sales – to the outskirts of Wisconsin’s capital city.
Start your night out with The Godfather: a cocktail with Chambord, vodka and pineapple juice. Dine on the 18-ounce Chicago Chop, pork stuffed with apple-herb dressing. See how the “steak house” and “supper club” experience overlaps.
Count bullet holes among evidence of a botched FBI raid here in 1934. “Little Bo” was a resort back then, hosting a gang of 10 mobsters and their molls. Dillinger, Nelson and others were on the run, and the FBI caught wind of their location.
But feds by mistake targeted innocent diners who approached a roadblock, which gave the real gangsters time to bolt in another direction. See what they left behind — from clothing to a machine gun — in display cases at the supper club. The atmosphere here is so perfect that Public Enemies, starring Johnny Depp, filmed the FBI’s surprise attack scene here.
With gambling upstairs and mobsters dining on the main floor, this supper club was a hangout for hungry gangsters. Being surrounded by red pines and next to Lake Patricia, this secluded area was a common hideout for the unlawful.
Legend has it this place is cursed — the wife of the original 1930’s owner lost out on the property in a bitter divorce and doomed bad luck to follow. After changing hands 15 times in 60 years, the current owners seem to have broken the spell. They’ve operated the club since 1995 and are still going strong.
For a delicious meal, Norwood Pines is known for its Filet Portabella, fabulous BBQ Ribs and the finest in seafood including seared Ahi Tuna.
Car chases and gunfire scenes from the 2009 thriller Public Enemies – the saga of John Dillinger, Baby Face Nelson and other elusive bank robbers – were filmed in Mirror Lake State Park. That’s where this beloved supper club is located, at the end of a remote road, facing the lake. “By Itself Alone” is the Winnebago translation of “Ishnala.”
Although no mention of underworld connections, Ishnala's owners talk up the site’s beginning as a log cabin trading post. And since the iconic atmoshpere caught Hollywood's attention and helped tell a classic gangster story, we couldn't leave Ishnala out of this list.