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The Pittsburgh History & Landmarks foundation has started offering free tours of the Old Allegheny County Jail Downtown - you know, the pretty stone one that ominously looms over Ross Street (featuring the Pittsburgh Bridge of Sighs).
While you are sure to learn more on the tour, for some basic information: the building was completed in 1886, and was the county jail until 1995. The structure is now the Family Division of the Allegheny County Court of Common Pleas. An area was preserved into the “Old Allegheny County Jail Museum."
The free tours occur every Monday (and some Saturdays). In addition, the Pittsburgh History & Landmarks Foundation offers several tours throughout Downtown, including the Cultural District and Mellon Square. A full calendar of events can be found online.