This article presents the Pilgrimage Model as a template for educators wishing to lead students on site-specific studies of engaged learning. During the 2015-2016 academic year, a group of Georgetown University students, faculty, and staff pursued the Pilgrimage Project, a year-long pedagogical experiment in interdisciplinary education and speculative design. Students researched Georgetown's historic Old North building from a variety of disciplinary angles and presented the results of their collective research in an on-site multimedia exhibit. The article analyzes the Pilgrimage Project from a practical perspective, as an effective means of delivering robust educational experiences, and from a theoretical perspective, as an example of speculative method in education research. As a model of interdisciplinary education, the Pilgrimage Model effectively merges disciplinary-specific course goals, in-depth student-led research, and student skill development in digital design and multimedia production.