In this paper, we use a day-long professional development workshop for higher education faculty conducted in an outdoor setting as the starting point for an examination of the value of such activities. We explore the potential benefits, in terms of learning and holistic well-being, of educational activities designed to provide participants with sessions either in the natural environment or the built (urban) environment beyond the four walls of the traditional classroom. Drawing on the literature of "place-based learning", the well-established traditions of some conference organizations, the emerging trend to mount such pre-conference workshops in the Society for Teaching and Learning in Higher Education (STLHE: Canada) and the feedback of past participants, we explore the nature of these experiences and the various outcomes, grappling with the challenge of identifying tangible "takeaways" at the individual and community levels. We conclude with directions for further analysis of the role of this type of session in terms of conference pedagogy and means of measuring impact on the well-being, outlook, and practices of instructors in higher education.