Conservation easements are among the fastest growing techniques for protecting land and open space. Conservation easements are legal agreements between a landowner and a conservation organization that limits or restricts entirely the right to develop a property in order to protect important conservation values associated with the property. At the heart of the conservation easement movement is the assumption that easements will protect ecologically important lands in perpetuity. However, there is little evidence that conservation easements can protect land permanently. Very few land trusts have experience in dealing with the myriad of challenges associated with long-term enforcement of conservation easements. This study sought to examine scenic easements acquired for the Blue Ridge Parkway in the 1930's and 40's and to develop an understanding of the challenges faced by the Parkway in attempting to enforce the terms of scenic easements drafted nearly 70 years ago. The scenic easements acquired for the Blue Ridge Parkways represent the first wide spread use of conservation easements in the country. The Parkway's early architects had few examples of easement programs to assist them in acquiring and managing these early forms of conservation easement nor did the NPS have the network of conservation organizations that exists today. This study reviews the process utilized by the Commonwealth of Virginia and the State of North Carolina to acquire scenic easements for the Blue Ridge Parkway and assesses the deeds used to convey the scenic easements from the states to the federal government. Further, this study evaluates and examines the number and types of violations of easement terms experienced by the Parkway and the various factors that may have contributed to violations of scenic easement restrictions and requests to alter/amend easements. This study also evaluates the various strategies used by the National Park Service to exchange and release scenic easements. Finally, this study concludes with a number of recommendations for improving the management of the Parkway's scenic easements and how organizations currently holding conservations can improve the stewardship of easements by incorporating adaptive management principles into their conservation easement stewardship programs. / Master of Urban and Regional Planning