Nick Montfort's "Winchester's Nightmare" premiered at Digital Arts and Culture '99 in Atlanta. The player character, Sarah, is based on the historical figure of Sarah Winchester (1837-1922). While the work is not meant to be an "accurate" portrayal of either Sarah or her infamous Mystery House (located in San Jose, California), the challenges that must be completed to successfully traverse this piece of Interactive Fiction (IF) are inspired by that past.

Specifically, without giving away the secret, in this work, the interactor must explore United City, which Montfort notes is "an American city" and "a 'mental map' of a character's psyche." And, as this IF world is mapped, it begins to resemble that of the United States, thereby giving the interactor a sense of familiarity in this simulated landscape. As with many pieces of IF, this world can be navigated via the points of the compass. In addition to physical space, this world recognizes the passage of time, which becomes essential to completing the assigned tasks.

In Twisty Little Passages, Montfort, quoting Jean Baudrillard, asks "What could be more seductive than a secret?" It is a question that the interactor should bare in mind when experiencing "Winchester's Nightmare."