The basis of this article is a workshop that the authors offered at the 2014 National Biodynamic Conference, which took place in Louisville, Kentucky. The workshop was titled “The Resettling of America”. It seemed appropriate to focus on the work of Wendell Berry, whose farm is located less than 50 miles from Louisville, and whose seminal work carried the prophetic title “The Unsettling of America”. The article follows the workshop in that it compares and contrasts Rudolf Steiner and Wendell Berry who through their writings and practice have presciently postulated a similar viewpoint decades ago. Steiner and Berry’s views foresaw many of today’s individual, socio-cultural, and ecological ills particularly in their relationship to agriculture.