There are many excellent histories of urban theater architecture; there are few that give us an understanding of actually being a concert or theater-goer on a particular night in 1855 or 1870 or 1903. What was playing? How did the inside of a theater look from various viewpoints? What was it like to sit with others in a crowded house?
Of course, scholarship and narrative description can represent such experience. For example, Thomas Forrest Kelly’s First Nights and First Nights at the Opera address some of these questions for specific premieres of musical works and operas. Vera Brodsky Lawrence’s monumental multi-volume Strong on Music re-creates the whole world of music and theater in New York City between 1840 and 1860, using George T. Strong’s mid-19th century diary and a detailed mining of journalism from the period.
However, there are also a number of digital approaches, a few of which I will note here:
Mapping the Moment is an interesting interactive map of theater and entertainment in Nottingham, England, in the 19th century, including performance venues, performances, and census information.
The Lost Museum, is an archive and re-creation of P. T. Barnum’s American Museum in New York City. The simulation lets you see and hear the museum's rooms, some of which contain historical commentary.
Virtual Vaudeville engagingly recreates New York City’s Union Square Theater in 1895. It’s a sophisticated simulation that allows you to experience a vaudeville show, in “real” time, while also exploring the space of theater.
For a related but different take on virtual recreation of entertainment venues, the Urban Simulation Team of UCLA creatied an architectural simulation of the 1893 World’s Columbian Exposition in Chicago. It needs people, but it's still pretty cool.
I’m only beginning to explore all this. If Ubisoft can bring 15th-century Italy to life, with attention to historical accuracy, in Assassin's Creed II, why not a night out in an antebellum city? For a scholarly summary of the issues, see Hugh Denard.