From its earliest days, The Contemplative Society was a catalyst for Cynthia Bourgeault’s international retreat work, hosting her pilot Wisdom School in 1999 and effectively launching what would become a global network of Wisdom Schools and retreats. As the Society’s capacity to fund a resident teacher shifted, the relationship evolved from underwriting Cynthia’s residency on Salt Spring Island to supporting and promoting her retreats and teachings worldwide. In more recent years, especially since 2018, Cynthia’s primary organizational home has moved closer to the U.S. East Coast through Wisdom Waypoints, while The Contemplative Society has focused on nurturing relationships with a broader circle of contemplative teachers. The event record presented here reflects that evolution: for the early years (1998–2005), documentation is sparse and has been carefully pieced together from whatever traces could be found; for 2005–2015, all known events are gathered into a single overview page per year; and beginning in 2016, when a digital event management system was adopted, individual events are listed separately, allowing for greater detail and traceability over time.