Academic conferences are events geared to disciplinary specialization, and much of the SoTL literature regarding scholarly gatherings addresses their benefits for graduate student apprenticeship. In our organization of the 22nd Annual International Conference on Virginia Woolf, we explored other forms of pedagogy to augment an academic professionalization approach. In particular, we created opportunities for cross-disciplinary teaching and learning, which have particular potential for Humanities students who may end up applying their discipline-specific training in non-academic contexts and in unexpected ways. This paper explores the possibilities and limitations of the cross-disciplinary initiatives that we developed for Interdisciplinary/Multidisciplinary Woolf. Inspired by the interdisciplinarity of the early 20th century British author Virginia Woolf and the current critical movement known as the New Modernist Studies, we outline the theories behind our approach to conference pedagogy and reflect upon our intentions and methods. We also assess learning outcomes in relation to both apprenticeship and non-traditional models of conference-based instructional design, and consider the institutional structures and practices that both enable and limit the scope of cross-disciplinary research and its dissemination at the undergraduate, graduate, and faculty levels. By moving away from the field of literary studies and sharing our scholarly teaching perspective in the context of the Scholarship of Teaching and Learning, we attempt to put into motion the potentially transformative disciplinary boundary-crossings that motivated the 2012 Woolf Conference.