Naming the oldest bar in a city like Pittsburgh requires us to first stake out the answers to some fairly arbitrary questions, especially regarding what constitutes a single bar. Is it the same bar if it was renamed? What if it kept its name but changed locations? What if it is in the same location, but the building was torn down and replaced? What if it was not operating at all for many years? How long a gap might it have and still be considered the same bar? (I take for granted that changes in owners, licenses, and style may be ignored, as any list would be virtually impossible otherwise.)
For my personal criteria, I prefer bars that have maintained basically the same name for most and preferably all its history. That is, it might have changed from the Queen City Saloon to the Queen City Tavern to the Queen City Bar and Grill or to Tom's Queen City Tavern; but it can't change to Viper Nightclub. It must have been in the same basic structure/building at the same location. It may have gaps of a substantial number of years -- e.g. during prohibition -- but not the better part of a century. It must have been a legal, licensed bar, as they are just far too complex to identify otherwise. But I shall also list bars ranked by how long there have been bars of different names in a given space.
I try to rely on primary sources - primarily contemporary city guides and newspapers, but will often use historical accounts if they seem to come from a historically reliable source. This does NOT include verbal histories from bar owners or staff, nor from newspaper or magazine stories that are not contemporary to the information they convey. I love input from these sources, but one finds them to be wrong at least as often as they are right when one can actually compare primary sources. Most notably, this is a work in progress, and I am most grateful to anyone who is willing to share corrections and more information - I can be reached at peterga@gmail.com
The Original Oyster House (1910)
Park House (1933)
Squirrel Hill Cafe (1934)
Evergreen Cafe (1936)
White Eagle Inn (1937)
Even in applying the personal criteria described above, naming the oldest bars in Pittsburgh is complicated. I consider the oldest, and the only one currently open that pre-dates prohibition, to be the Original Oyster House. According to Rick Sebak, the Oyster House was established in 1870 on a nearby corner, and moved to its current space in 1871 - a space he says was previously the home of the Bear Tavern, which opened in 1827. But I do not know what its exact name was at the time, nor when it first added a bar. To complicate matters further, subsequent owner Lou Grippo acquired two adjacent buildings in 1972, remodeling and merging them, and I do not know the location of the bar portion in the years preceding this.
One source says that Hughie Lynn named and started the Oyster House about 10 years before Louis "Silver Dollar Louie" Americus purchased it, which would have been circa 1905. It was called the "Old Oyster House " at least by 1918, when Lynn sold it Max Srolvitz. As for a bar, one great advantages for this sort of research in the Pittsburgh area is that contemporary newspapers, now readily available in online archives, printed very comprehensive lists of liquor license applications from the 1880s up through the first few years of federal prohibition. The first such application I've found from the location of the Oyster House (which could be listed alternately over the years as 5 McMasters Way, 7 McMasters Way, 2-4 Masters Way, 2-4 Drummond, 17 Market Square, or 20 Market Square) is from by Hugh Lynn, which would have put it at exactly the point at which the Pittsburgh Sun-Telegraph 1946 article dates its founding.
Thus I date the Original Oyster House bar to 1910, and consider it the oldest bar in Pittsburgh by some measure. If one requires that it be named exactly "Original Oyster House," this name becomes listed in 1933.
Other Oldest Bars
So what bar is next oldest? Before I describe that, allow me to correct a story about one bar that is close. A 4/17/2023 article in the Pittsburgh City Paper repeats a story from the bar owner dating the Evergreen Cafe to 1933, noting that "The bar has been in Point Breeze since 1933, when it was relocated from Wilkinsburg after Prohibition was lifted, since Wilkinsburg remained a dry municipality." However, this is not quite accurate. As the Jan 2, 1936 issue of the Pittsburgh Post-Gazette explains, the Evergreen was actually denied a license renewal in Wilkinsburg on Jan 1, 1936, after Wilkinsburg had voted Dry in November 1935. This combined with the cafe being listed first among Pittsburgh bars and at its current address in the 1936 Polk Directory make it quite clear that this was the year it moved a few blocks and officially into the city, placing it at #4.
Sorting out #2 and #3 is considerably less clear. The Squirrel Hill Cafe (AKA Squirrel Cage) has been said by previous owners and articles to have been established in 1933, sometimes claiming the 2nd Allegheny County post-prohibition liquor license, issued June 1, 1933. Unfortunately, old liquor license data from after prohibition is much more difficult to come by, and I haven't seen any artifact or primary source to confirm that (I have not been able to locate a 1933 Pittsburgh Polk guide). A mentions "There has been a restaurant on the premises since 1933 when the predecessor of the current Park House opened." Does "predecessor" mean it started under a different name? I've heard many, many dubious and often conflicting stories about the "oldest liquor license in the state" and etc., so I remain less than 100% confident, but at least for now I will date the Park House to 1933.
Various histories of the fabled "Squirrel Cage" date the bar to 1934, and city guides confirm this. It seems to have been commonly referred to as the "Paterni Restaurant" until at least May 1934, but as the "Squirrel Hill Café" by at least Oct 1934, and probably earlier given that Polk Guides are assembled early in the year.
The appealingly divey White Eagle Inn changed to its current name from Comsick's Cafe sometime between 1937 and 1938.
If we are to allow name changes, which current bars reside in locations that have hosted bars for the longest times? Again, if we accept the verbal history of Rick Sebak, and if we assume it fits the other criteria I have mentioned, the Original Oyster House resting in the 1827 location of the Bear Tavern makes it the oldest I've heard of by a considerable measure. However, if we rely more on the very good license data from the 1880s to 1924, we see at the very minimum that the location went for some time with no bar. When I rely on cases I've able to confirm with this data, the oldest I've found is the South Side Primanti Brothers, at 1822 E Carson, which hosted the saloon of J.W. Ruhlandt beginning in 1885. This is followed by Brewskis and The Goldmark, which hosted saloons at least as far back as 1888.
These rankings have considerably more uncertainty than even the ones above, and I expect them to be updated and corrected more frequently. But below I present what I've been able to find by working backwards from a list of current bars with a significant history of bars at the same address. Again, I heartily welcome any corrections, additions, and other relevant information.
Note: "OE" stands for "Or Earlier" - i.e. the bars were there by the given year but could have been there a bit before that as well.