As entrepreneurs, we’re often told to embrace the unknown and venture into uncharted territories. In Milwaukee, some innovative business owners have taken this advice to heart, turning the city’s ghostly past into thriving enterprises. From speakeasies to haunted houses, these entrepreneurs have found unique ways to blend history, mystery, and commerce, creating experiences that captivate locals and tourists alike. Their stories serve as a reminder that with creativity and vision, even the most unconventional ideas can become successful ventures, echoing the spirit of innovation championed by the Lubar Entrepreneurship Center community.
Halloween in Brew City
October 31st. Halloween. A day shrouded in a crushed-velvet robe, clouded in mist and mystery. Spirits roam alleyways after rainstorms, and haunted hollows begin to howl as the lives of the undead and the living intermingle once more. Claims of the paranormal and supernatural have always been a vital piece of our legacy. From stories of Loch Ness monsters to wild witch hunts and vengeful spirits who roam rivers, these tales have lived on for thousands of years. And while some proclaim these stories as hoaxes, during the month of October, they pique interest across the world. Lucky for Milwaukee residents, these mysterious encounters are deeply rooted in our history and continue to influence businesses today. Therefore, with Halloween soon approaching, we want to shed light on a few of Milwaukee’s most haunt-worthy businesses.
Shaker’s Cigar Bar and Speakeasy
One of the only places where past and present waltz in harmony within the modern-day era, Shaker’s Cigar Bar and Speakeasy is renowned for its commitment to the unknown and embracing its mysterious history, earning it the affectionate title of “the Cultural Museum.” From being a Prohibition-era speakeasy owned by the Capone brothers to a frequented location for other notorious Milwaukee figures, Shaker’s is not afraid of its ominous past.
We had the opportunity to sit down with owner Bob Weiss to discuss his experiences with the paranormal and his ability to flourish with the unknown. We focused on his encounters within the walls of Shaker’s itself, including the apparitions known to frequent the building, such as the young girl Elizabeth, who inhabits the bathroom, and O’Conner, an Irish Confederate soldier who resides in the cellar. For those brave enough to spend a night in the upstairs brothel from the Prohibition era, Bob warned that only about 15% of visitors make it until dawn. He remarked, “Whatever it is that you’re afraid of, some things will prey upon that.”
The foundation of Shaker’s and Hangman Tours (a historic tour company owned by Bob with tours in Milwaukee, Savannah, and Los Angeles) is rooted in the belief that “You can’t forget about your past.” A poignant statement in our fast-developing world. Bob extends this sentiment well beyond the curated wood walls of the speakeasy as a world traveler dedicated to uncovering stories of the past— “the fabric of who we are”—and raising awareness for the beyond.
Despite its chilling history, Shaker’s ambiance is incredibly welcoming. Patrons laugh throughout the evening, converse with staff, and greet Bob, creating an unmistakable connection to the space. When I asked about what it takes to join Shaker’s staff, he noted that his 30-person onsite team must attend the ghost tours and spend time in the cellar alone before their first shift. Thanks to these pre-screenings, Bob has confidence in his staff, and turnover is low, adding to the almost familial bonds that fill the space ghosts do not occupy.
Overall, Bob assured us that the spirits are content, and with the relaxed, fun-loving energy of the location and clientele, it is easy to see why. Besides his testimony, my coworker and I were unnerved by a small door that opened and closed frequently during our stay despite no one appearing. But one should not just take our word for it; as Bob said, “If your eyes are open and you want to get something, you’ll get something.” Whether hoping to encounter the beyond or simply looking for a mature dining experience, Shaker’s Cigar Bar and Speakeasy is worth a visit no matter the season.
Novak Manor
While the Novak Manor is not haunted itself, thanks to the vision and hard work of Patty and Adam Novak, it transforms into a frightful sight throughout October. Despite a few challenges this past year, the Novaks are dedicated to supporting their community and providing a frightfully fun experience for all!
On Fridays and Saturdays from 6-10 PM, Novak Manor becomes a completely volunteer-run haunted house featuring jump scares, spooky decor, and scare actors. Admission is a minimum dollar donation, supporting Bikers Advocating Child Safety (BACS) and other West Allis community programs. This haunt includes an array of classic horrors like clowns and Michael Myers. To make the Halloween spirit accessible to all, they provide glow sticks to signify those who do not wish to be scared but still want to immerse themselves in the experience.
The Novaks’ dedication is evident and appreciated by the organizations they support. Their generosity as a seasonal, home-based nonprofit shows that, no matter the time of year or who you are, giving is always in season.
Milwaukee’s Haunted Ventures in the Spirit of Halloween
In Milwaukee, the entrepreneurial spirit thrives as innovative business owners transform the city’s haunted history into captivating experiences. Venues like Shaker’s Cigar Bar and Speakeasy and Novak Manor blend ghostly tales with modern entertainment, inviting locals and tourists alike to explore the unknown. As Halloween approaches, these unique businesses remind us that with creativity and vision, even the most unconventional ideas can flourish. Embracing both the eerie and the entrepreneurial, Milwaukee showcases how history and mystery can create a vibrant community spirit during this haunting season.