Look into the origin of the speakeasy, and you’re bound to come across Kate Hester, owner of an illegal McKeesport saloon. The legend, captured in an 1891 New York Times article, goes that when Hester’s customers, “a boisterous lot,” got too rowdy and risked drawing police attention, she would wag her finger and whisper sharply, “Speak easy, boys! Speak easy!” The expression took hold around the region, standing in for any illicit establishment that sold alcohol, and then made a national splash in the Times, giving Pittsburgh the dubious honor of coining the term.
Speakeasies are most associated with the Prohibition era, which, from 1920 to 1933, saw a nationwide constitutional ban on producing, transporting, and selling alcohol. But in Hester’s time, decades before Prohibition, Pittsburgh’s speakeasy culture was already flourishing. A Pennsylvania law enacted in 1888, the Brooks High License Act, raised saloon licensing costs and limited their hours of operation, a restrictiveness still reflected in today’s state liquor laws. (According to Pittsburgh Drinks: A History of Cocktails, Nightlife & Bartending Tradition, Hester herself was rejected for a license, then granted a hearing where she presented a letter from her pastor attesting to her “good name.”)
By 1890, Pittsburgh was home to 700 speakeasies, the first to emerge in America. Described by the Times as “the illegitimate child of the Brooks high-license law,” there were speakeasies across every neighborhood in the city and floating on its rivers.
“The commonest item in the police news of Pittsburg is the raid of a ‘speak-easy,’” the paper wrote.
More than a century later, speakeasy bars remain alive and well in Pittsburgh. Revived about 25 years ago in Manhattan, the speakeasy-style bar is a nationwide trend credited with repopularizing craft cocktails in America. Though today’s speakeasies are sanctioned, they still try to evoke the hidden quality of their predecessors with secret doors, peepholes, passwords, and low-lit 1920s decor.
Some argue the trend has peaked. In 2019, Commerce Bar in East Liberty gained national attention with a Forbes article titled “Try This New Speakeasy In... Pittsburgh, Pennsylvania?” Others contend that speakeasies have gotten too kitschy — after all, the speakeasies of yore could be violent and dangerous.
But the bars have expanded from the city to the suburbs, still drawing patrons looking for premium cocktails, a sense of history, and even a bit of gadgetry.
Pittsburgh City Paper looked into the speakeasy’s contemporary legacy and what it offers bargoers today.
At Speakeasy in the Omni William Penn Hotel, the name isn’t a misnomer. Tucked under a stairway beneath the hotel lobby is a bar that, during Prohibition, was a booming speakeasy.
“We love having this room,” Bob Page, the hotel’s area director of sales and marketing, tells City Paper. “I don't know how many [original speakeasies] are truly left in the city of Pittsburgh … I wish the walls could talk because we want to know what’s gone on in here. I'm sure a lot.”
Page has worked at the Omni William Penn for 23 years and helped facilitate Speakeasy’s renovation. When he started at the storied Downtown hotel, the room reputed to have a speakeasy had been boarded up or used as storage for 50 years. Hotel staff pried open its doors to find a mahogany bar, flocked wallpaper with pink and beige flowers, and a cracked terracotta floor.
To restore the speakeasy “into its former historic glory,” the hotel “basically duplicated the [existing] look and the wallpaper,” Page says. The bar, kept in its original contours, retains rich brown wood and has plush noir-style red seating, all enclosed by a tin roof.
The hotel incorporated other historical touches. Page was contacted by a former pharmacy in Bloomfield that found 1920s prescriptions for “medicinal liquor” in their basement. During Prohibition, a carveout by the U.S. Treasury Department permitted doctors to prescribe alcohol on special watermarked forms. The old prescriptions — including a pint of whiskey given for insomnia — now hang in Speakeasy.
“It's funny because they look like little college degrees,” Page says. “But you could get a doctor to prescribe booze for you.”
Behind glass at the bar is a whiskey bottle bearing the William Penn Hotel crest dated April 7, 1913, three years before the hotel opened. Page discovered that the whiskey came from the Overholt Distillery, owned by the Frick family, who opened the William Penn.
“[Henry Clay] Frick had a massive ego, right?” he explains. “He was determined that if he was going to build this opulent, luxurious hotel, he was going to have booze on hand to open it. So he had his grandfather start distilling alcohol for him before they even broke ground.”
After Prohibition was ratified seven years later, Page believes it’s likely the hotel’s speakeasy required a password and would’ve been raided several times.
“No speakeasies ever kept records,” he says. “But the other side of that [is] you’ve got to believe [Frick] had a relationship with the police because of his wealth and stature.”
Almost a century later, Speakeasy opened on Dec. 5, 2012 — the anniversary of Prohibition’s repeal — then at the forefront of the speakeasy bar trend in Pittsburgh.
“That demographic of younger people are looking for an experience,” Page says of the bar’s appeal. “I think that history part of it is something that's intriguing to them. They love to say, ‘Hey, I'm in a room that illegal booze used to be served in and nobody knew about it.’”
The Speakeasy menu pays homage to its roots with specialty cocktails named Password, Bathtub Gin, and The Prickly Bootlegger, alongside classics like the Old Fashioned and Tom Collins.
Adding to the clandestine feel, the windowless bar only seats 45 people. Recently, the hotel opened an additional room to host larger events, part of a strategy to rebound after COVID shutdowns. Page says that, when Speakeasy opened in 2012, its primary patrons were hotel guests, but they’re appealing more to locals, particularly as Downtown grows its residential population. Adding more live entertainment like jazz and expanding food options are all intended to keep Pittsburghers coming to the bar.
“I just think that it’s unique [and] that it’s one of the coolest places to be able to sit and have a cocktail in the evening,” Page says. “[It’s] just getting people aware that it’s here for them.”
In Homestead’s historic Bank On 8th building, another speakeasy bar quietly opened in 2021. Though the former site of the PNC Bank and Monongahela Trust Company, which was built in the 1920s, didn’t house a speakeasy that he knows of, owner Joe Deasy Jr. tells CP there are definite historical parallels.
When he and his father renovated the building during pandemic liquor store closures, “we jokingly [said] there’s only been two times in U.S. history that there’s been Prohibition and we were open for one of them.”
Co-Sign Speakeasy, billed as an immersive cocktail experience, is Deasy’s third venture in the century-old bank building following Escape Room Pittsburgh and Ace Axe Throwing. At first glance, the businesses may seem disparate, but each offers an “immersive entertainment experience,” Deasy’s favorite market.
“No matter which experience you choose in the building, you can put your phone down, relax, and enjoy your night out,” he says.
Deasy and his family started Escape Room Pittsburgh with its first location in Greenfield nearly a decade ago. Then a niche entertainment option, the Greenfield escape room was touted as the first to open in Pittsburgh and, Deasy believes, among the first 20 escape rooms nationwide.
Spearheading that trend presented many hurdles — as Deasy recalls, the building inspector “was like, ‘you’re locking people in a room?’” — but continued interest inspired him to “keep building,” he says.
Unlike his experience opening the escape room, guests already understand the concept of a speakeasy bar.
“I personally like the speakeasy trend,” Deasy says. “You know you’re going to get fancy cocktails in a really themed room. So that was the vibe that I wanted right out of the gate.”
In Homestead, “we had this weird room in the building,” Deasy says. “I always knew I wanted to do a fancy cocktail bar somewhere … but I thought we had a good spin where we could incorporate some escape room technology into the bar.”
In contrast to the low-tech “ultimate urban getaway” promised by the Omni William Penn, Deasy imagined a “labyrinth of hidden doors.” He’s adamant that speakeasies need two elements: fancy cocktails and a hidden entrance, “one of the staples.”
Co-Sign Speakeasy — named as a nod to bank loans — is on the fourth floor of the building, and you can’t walk right in. Guests ride in an elevator covered in damask wallpaper similar to the bar’s, going past one of the original bank vaults. Entering the fourth floor, the space is styled like the former Monongahela Trust Company bank lobby, with safety deposit boxes, a bench, a desk, and other furniture (all of which double as puzzles in the escape room).
Winding a large clock to a certain time rolls back a hidden door — otherwise a beige wall — to reveal the dark cocktail bar with vintage red seating similar to the William Penn. A gold-flecked ceiling was plastered by three generations of Deasys. Old banknotes recovered from the building make up the bar top.
Describing himself as a “technology guy,” Deasy says, “I love doing the electronics, the hidden gizmos and gadgets.” The speakeasy’s bartender can also push a button to raise a hidden wall, concealing the bar’s liquor shelves, and the space adjoins three other themed rooms, one of which is accessed through a hidden bookcase door, among other tech flourishes.
Deasy also hopes to pay homage to the building’s history and “the roots of the speakeasy in Pittsburgh.” The Red Room features historic photos etched into the windows that show the skyline of the Homestead Steel Works from the same vantage point 100 years prior.
“It was a real historical spot … and it kind of has a nice view of the waterfront,” Deasy says. “We always [thought] wouldn't that be cool if people from the bank enjoyed a cocktail up here?”
Speaking of cocktails, Deasy wanted a “take on new cocktails with the old cocktail spirit in mind." In addition to Prohibition-era cocktails, including a sidecar and Sazerac, Co-Sign’s signature drink is a smoked Old Fashioned, a flaming cocktail that can be ordered with whiskey, bourbon, or tequila.
The modern speakeasy comes with its share of ironies. For example, both Speakeasy and Co-Sign serve non-alcoholic beverages. The latter establishment touts a full mocktail menu, now a trend among sober-curious Gen Z. Deasy is also aware that enjoying a fancy drink with a retro rotary phone means offering an “Instagrammable experience,” and guests come explicitly to share photos of the once-covert speakeasy. Advertising a speakeasy poses a conundrum, because “by design, you can’t put a billboard on the side of the building,” Deasy says.
But Pittsburgh’s affinity for the speakeasy, and immersive entertainment at large, shows little sign of slowing.
“I’m not going anywhere,” Deasy says, noting that people enjoy being transported out of the everyday. “We took themed elements from the 1920s, ‘30s, ‘40s … and wanted to take people on an adventure.”