Pittsburgh was once a seedy river city. The three rivers once floated an armada of criminal activities: bootlegging, gambling, prostitution, and theft. Fortunately, the only pirates in the city’s history were its sports teams (though some today might say that the Buccos’ recent performance is criminal). The rivers were like the rest of the city at the time — vice operated openly and became part of Pittsburgh history and lore.
While other cities leverage their seedy stories to attract tourists and to engage riverside spaces, Pittsburgh tends to overlook the opportunities to drop anchor in its criminal history and fish for stories to sell the city.
“The simple view is that, without these rivers and without these river valleys, there is no Pittsburgh,” says Rivers of Steel historian Ron Baraff. “Back in steamboats and on the sternwheelers and using the Mon Wharf, for example, a docked sternwheeler … becomes a river-based playhouse. And I mean that in all sense of the words. But also for gambling and drinking in restaurants all the way up through where we are now.”
Riverlife executive director, Matthew Galluzzo, believes some individual organizations do a good job describing how Pittsburgh’s rivers that fit into the city’s steel, glass, and shipbuilding history. But he thinks the city could do a better job telling a more complete story in ways that are educational and fun.
“Could we do a more transparent or ubiquitous approach to that?” Galluzzo wonders. “Could we have more interpretive signage and [could] every region … reinforce their history in meaningful ways?”
But when it comes to how Pittsburgh leverages its vast riverfront spaces for entertainment — there are about 35 miles of riverbank just inside the city alone — he thinks the city might be adrift and could do things better.
Not too long ago, creative entrepreneurs found numerous ways to entertain and generate profit while floating on docked boats and barges. Those pleasure palaces drew upon a pivotal point in Pittsburgh history when, in 1831, William Chapman launched the Floating Theater, the nation’s first showboat, down the Ohio River.
It didn’t take long for copycats and other innovators to create a small fleet of showboats moving from landing to landing on what were then called the Western Rivers, the Mississippi and Ohio rivers and their tributaries.
Showboats, casinos, speakeasies
Showboats plied the three rivers for much of the 19th and 20th centuries. Though they frequently stopped at Monongahela River coal mining towns early on, by the mid-20th century, most showboats began or ended their annual seasons here in Pittsburgh. “The complete showboat circuit, start[ed] each year at Pittsburgh or even up the Monongahela, and end[ed] at New Orleans,” wrote historian Philip Graham in his 1951 book, Showboats: The History of an American Institution.
The Gateway Clipper fleet’s excursion boats are replicas of earlier steamboats that once carried mail and people from New Orleans up the Mississippi and Ohio rivers. Though many of those early sternwheelers featured entertainment during trips, showboats were a special breed. They copied some of the architecture of their self-propelled cousins.
“The smaller ones look like old-time packets with their smoke stacks knocked off, and the larger ones like two-story Pittsburgh apartment houses,” Graham wrote. Some of the larger boats could host more than 900 people at a time.
“A showboat would be like … a theater built on a barge,” retired riverboat captain Donald Sanders tells Pittsburgh City Paper. You go inside, and there would be the stage, and there would be an auditorium.”
Showboats were towed from landing to landing, where their arrival would be announced by a calliope playing “Here Comes the Showboat.” People on the banks of the Ohio, Monongahela, and Allegheny rivers could hear the tune for miles. They would make their way down to the Mon Wharf where they could see a play, vaudeville act, or band concert.
Several notable showboat owners hailed from or called Pittsburgh home. Ralph Emerson Gaches was a natural-born entertainment huckster. The son of a popular railroad conductor, Gaches spent the first years of his life on the North Side. After his mother died, James Gaches remarried and moved his family to Letart Township in Meigs County, Ohio. There, Ralph got his first taste of Ohio River life. As a teenager in the mid-1890s, he ran away from home to sign onto a riverboat.
By 1898, Gaches was working on Price’s Water Queen showboat, which made regular trips to Pittsburgh. Within a decade, Gaches had worked his way up from distributing show flyers to managing the Water Queen and in 1906 buying his own showboat, Emerson’s Grand Floating Palace. By that time, he was calling himself Captain Ralph Waldo Emerson. “He dropped his surname because he insisted no one could pronounce it and because Emerson was a distinguished name,” recalled showboat captain Billy Bryant in his 1936 memoir.
Novelist Edna Ferber spent time on one of Gaches’ former boats, the Goldenroad. She drew on the experience to write Showboat, which became a hit Broadway musical in 1927 and a movie in 1951. Ferber named her fictional showboat after another former Gaches boat, the Cotton Blossom.
Captain Tom Reynolds was another showboat owner with strong Pittsburgh ties. Three generations of his family operated and performed on his popular showboats, which included the Majestic. Built in 1922 at an old Monongahela River coal landing near the Glenwood Bridge, the Majestic became one of the last working showboats in the United States. In 1989, it became a National Historic Landmark.
Shantyboats
Not all the flat-bottom boats tied up alongside the three rivers were working barges or entertainment venues. Decades before unhoused people sought shelter along the city’s river trails in precarious encampments, people lived on a type of houseboat known as a shantyboat.
Pittsburgh has a long history of people experiencing homelessness. As early as 1907, the sociologists who produced the multi-volume Pittsburgh Survey recognized the problem. It was “worse than no provision by the city itself, sporadic and ineffective oversight of private establishments, summed up the public policy toward homeless men in this city to which thousands come annually,” wrote sociologist Paul Kellogg at the time.
Many of the city and surrounding area’s unhoused found temporary shelter in downtown boarding houses. “Garages, stables, henhouses, and even a cave were turned into dwellings,” the Pittsburgh Housing Association wrote in a 1938 report. Because of laws that stigmatized unhoused people, many also found themselves incarcerated in the Allegheny County Workhouse.
Unhoused people and families unable to afford even the most substandard housing also turned to the rivers for shelter. They lived on repurposed barges and boats, many of them abandoned along the city’s extensive riverbanks.
The vessels were called shantyboats. “A shanty boat is a scow with a small house on it,” wrote Kentucky artist and author Harlan Hubbard in his 1953 book, Shantyboat. Like Cincinnati, St. Louis, and other major river cities, Pittsburgh’s three rivers and substantial riverboat traffic made shantyboat life a viable alternative to squatting in abandoned buildings.
In the 1890s, a substantial shantytown emerged along the Ohio River in Cincinnati. Squatters living on shantyboats and in shacks had been there for more than 20 years before the city displaced everyone and burned the encampment in 1913. It was a temporary solution – in a cycle familiar to many people today, the shantyboats returned.
Historian Susan Morris wrote about the Pittsburgh’s shantyboat dwellers in a 2018 blog post. “The enterprising river citizen was as likely to scavenge, commandeer and spruce up an abandoned barge as he was to lay out cash for a ‘new’ vessel,” Morris wrote.
“You need a place to live and you don’t have a job, you don’t have money,” Morris said in a 2024 interview about some of the people who lived on Pittsburgh’s rivers. “I really think it was necessity … This wasn’t sort of the Gilded Age saying, ‘Oh, I’d like to live on the water.’”
Snake-oil salesmen
Pittsburgh’s riverfronts also attracted medicine shows and fly-by-night fraudsters who plied their trades while moored here. Medicine shows were popular traveling troupes in the 19th and 20th centuries, and featured actors and musicians who could draw a crowd. The goal, though, wasn’t entertainment – medicine show owners used the entertainers to lure potential buyers for patent medicines and so-called miracle cures that could fix anything from digestive issues to sexual performance and baldness.
“Hundreds of patent medicine peddlers, fortune tellers, clairvoyants, and voodoo practitioners did a brisk business in river cities,” wrote historian Gregg Andrews his 2023 book, Shantyboats and Roustabouts: The River Poor of St. Louis, 1875-1930.
Before the Bryant family, whose boats regularly visited Pittsburgh, cast off on their showboats, several members performed with medicine shows. They played guitar and performed magic tricks before launching their successful showboats, after spending a season on Price’s Water Queen while Gaches was its manager. While back on the medicine show circuit, they ended up in the Allegheny River town of West Hickory. There, Sam Bryant built his first boat to take their mules, wagons, and themselves downriver. Back home in West Virginia, in 1907, the Bryants launched their first 140-person capacity showboat, the Princess.
Some medicine show hucksters found clever ways to stay afloat. One of the nation’s best known, Madam Clifford, worked the medicine show and theater circuit in the early 20th century. By 1911, she had settled down on a houseboat docked in Homestead where she offered readings in person and by mail order.
For 10 cents, people could send her a stamp and their birthdate. In return, Madam Clifford would send what she called a “trial reading.” Folks in Pittsburgh could drop by: “Madam Clifford will give clairvoyant and business readings at foot of West Street, on medicine boat, Homestead,” read her ads published in local newspapers.
“Depravity” and “perversion”
After Prohibition began in 1920, cabaret and restaurant owners like Frank Bongiovanni moved some of their operations onto local river, where patrons found booze, music, and fine food bobbed atop barges converted into floating nightclubs. Bongiovanni’s Floating Palace, launched in 1923, became the most infamous.
In 1929, gambling entrepreneurs George Jaffe and Art Rooney leased Bongiovanni’s boat from the John Eichleay Jr. Company and renamed it the Show Boat. Federal agents raided the Show Boat in May 1930, seizing booze and gambling gear after passing by Pittsburgh police officers hired by the gamblers and who were posted at the gangplank.
The week before the Show Boat raid, local law enforcement officers raided the Manitou. Like the Show Boat, it, too, was owned by the Eichleay company. A few years earlier, Gaches had sold the Manitou and its towboat, the Red Wing, to Eichleay after a major refit done at the company’s Hays boatyard.
The May 5, 1930 raid on the Manitou yielded a trove of adult films and gambling paraphernalia. It was a time of flappers and of pushed boundaries, with dancers flouting morals laws with increasingly skimpy costumes.
“County detectives raided the barge … which for months has been the scene of shows in which the costuming of the chorus hasn’t been any problem to the promoters because there weren’t any costumes,” the Post-Gazette reported.
Muckraking journalist Walter Liggett was in town when both raids went down. “There isn’t a form of depravity that hasn’t been put on a dividend-bearing basis in Pittsburgh, and even perversion is made to pay a profit,” Liggett wrote in a widely read magazine article. “For months a boat called the Manitou, which docked in the Monongahela River near the foot of Wood Street, pulled out into the river every night with from three hundred to five hundred cash customers aboard and a nightly ‘show’ was put on which consisted of naked dancing and indescribably vile motion pictures.”
Floating back to the future
Much of Pittsburgh’s early colorful culture has disappeared. There are no historical markers that tell the stories of Pittsburgh’s showboats and floating casinos. Except for the Kamin Science Center’s Requin submarine and the Rivers of Steel’s Explorer riverboat, there are no historic boats moored along the rivers that tell this story. In fact, it’s possible to get more of Pittsburgh’s riverfront history 470 miles downstream in Cincinnati. There, in a popular riverfront park, historical plaques in the Riverboat Hall of Fame discuss Pittsburgh boatbuilding and its role as a riverboat destination.
Though the technology and uses are different, vestiges of Pittsburgh’s past as a dominant river city survive. When Alan Bernstein’s family went into the riverboat business in 1979, they bought their first boat from Gateway Clipper. “We have bought several things from Gateway over the years,” says Bernstein, whose excursion boats are based in Newport, Ky. across the Ohio River from Cincinnati.
The old Gateway Clipper boat wasn’t the Bernsteins’ only tie to Pittsburgh. Between 1977 and 2008, the Bernsteins operated a restaurant docked in neighboring Covington, Ky. Named the Mike Fink after a legendary 19th century riverboat operator, the sternwheel steamboat was built on Neville Island in 1936. Originally it had been named for Pittsburgh foundry and riverboat owner John W. Hubbard.
With city- and county-led removals of the encampments that succeeded shantyboats, the slow gentrification of old industrial sites, and the arrival of new family-friendly entertainment venues like Riverlife’s Shore Thing, Pittsburgh’s riverfronts would be unrecognizable to a 1920s steamboat captain.
And many believe erasing or forgetting Pittsburgh’s colorful riverfront history is a lost opportunity. “I think we’re completely under-leveraged in terms of utilizing our waterways for entertainment,” says Riverlife’s Galluzzo. “I think, with a little bit of effort, folks can really access a clear and, in some ways, objective view of that history.”
This article appears in Oct. 15-21, 2025.
