Sustaining agricultural environments requires explicit recognition of the services provided by landscapes, particularly cultural ecosystem services that are contested and underrepresented in previous research. We assembled and engaged a panel of experts to identify and deliberate on the relationships among ecosystem services, threats and land management practices in an agricultural watershed using a Delphi method. We also drew from focus group results to gain an in-depth understanding of how participants valued the Kaskaskia River Watershed, Illinois. Results revealed that diverse benefits were derived from provisioning (e.g., crop production), regulating (e.g., flood prevention), supporting (e.g., soil formation), and cultural (e.g., farming lifestyle) services provided by the watershed. A disproportionately higher number of cultural services were identified and rated as highly important. Multiple threats, including erosion and nutrient loading, were associated with agricultural, forest and lake and river environments, highlighting the importance of connectivity across ecosystems. To mitigate and adapt to change, particularly around the provision of agro-ecosystem services, stakeholders benefit from collective discussions about land management practices such as reduced tillage and zoning policies. Engaging local stakeholders in deliberation provides a rich basis for understanding the multiple values of worked landscapes and establishing sustainable agricultural practices.