The Coffee Cultural Landscape of Colombia exemplifies the historical, cultural, economic, ecological, and symbolic heritage values of an agricultural landscape. Its inscription as a World Heritage Site elucidates the complexity of safeguarding traditional agro-ecological systems of production threatened by changes in land use, urbanization, farming techniques, and environmental change. Coffee has been the quintessential crop sustaining rural livelihood in Colombia and a main driver behind the country´s development. It is a national symbol, and an internationally recognized high-value commodity. The Coffee Cultural Landscape has the ideal environmental conditions and knowledge to continue producing some of the best coffee in the world; however, the cultural and ecological values of traditional farming practices have yet to be articulated and incorporated into the site´s management. This study proposes a framework for assessing the heritage values of small-scale farms in the Cultural Landscape based on conditions, adjacencies, and connectivity. It considers three different scales for understanding agricultural areas as their function and public benefits change in relation to their surrounding context. Articulating the cultural and ecological values of cultivated lands should serve as a platform for fostering stewardship and responsibility, and for creating incentives and constraints to ensure the continuity and vitality of the Coffee Cultural Landscape.