This article presents the results of a semester-long project designed to determine how effectively interactive Web 2.0 technology can facilitate collaborative research in undergraduate learners. The study was conducted during a 2007 advanced Shakespeare course at the University of Central Florida that focused heavily on a new historicist approach to studying literature. In this paper we first establish the theoretical foundation for this particular approach to literary studies, then discuss more in-depth how the collaborative, inter-connective nature of wikis allowed students to witness first-hand some of the concealed assumptions enmeshed in the creation of historical explanation or narrative. We also discuss how, in thinking about the past, this technology allowed our students realize some of the stakes in describing history for the present. In other words, having students create wikis based on the social identities that recur in Shakespeare’s works developed an implicit awareness of motives for "doing" history. We also show how employing open source technology in a localized classroom setting can assuage some of the gaps we experience in trying to provide enough period coverage while also attending to theoretical apparatus and students’ experience of meaningful connections to material. On a larger scale, creating inquiry-based projects can alleviate some of the humanities’ disengagement from the "real world" that many have been suggesting of late.