What happens to our understanding of food production when we shift from a land to a landscape perspective? How might a landscape perspective enrich the possibilities for regenerative agricultural outcomes? How might food systems leaders promote and plan regenerative landscapes? This chapter pursues these questions by first reviewing contemporary theories of landscapes as active and performed places with diverse outcomes. We then consider the implicit role landscape already plays in regenerative agriculture systems. Our planning discussion draws on working landscapes policy enacted in the state of Vermont and a case study of Vermont’s booming cider industry. Our analysis highlights the promise of working landscape policy approaches for engaging public support for progressive food production policies. We also identify the weaknesses of a policy that fails to realize its full potential to enhance regenerative processes due to a lack of attention to scale, distance, and place. The chapter closes with recommendations for including a landscape perspective in planning regenerative agriculture systems.