From Washington, DC to the Chesapeake Bay, there is a landscape rich with natural resources, sensitive habitats and wetlands, cultural and historic sites and rural character. This same landscape is also under pressure from intensive land use and regional development, which not only consumes valuable land resources, but also degrades the health of the Bay. Consequently, federal, state and local governments are finding new ways to preserve land as a way to protect the Bay, as well as the unique natural and cultural resources embedded within its watershed. Land preservation programs have been successful in protecting large undeveloped tracts in order to preserve agricultural enterprises, natural areas and fragile ecosystems, public lands for recreational and educational purposes and significant historic and cultural sites. As development pressure mounts and suburban sprawl takes root in rural areas, the need to protect land is far outweighing the available resources of many land preservation programs. This requires that programs have focused agendas, efficient day-to-day operations and the ability to draw on the capacities and resources of other disciplines. Even though land preservation programs have the management capacity to target and protect large pieces of land under their agency, all too often they fail to realize new opportunities in establishing strong working relationships with other fields. This is partly due to the fact that they must focus narrowly while advocating for additional funding from federal or state agencies. Additionally, many land managers operate within organizational silos and miss the opportunity to collaborate across disciplines. Identifying overlaps between fields with shared goals and similar operational activities can be used as one way to increase the ability of land preservationists to protect valuable undeveloped areas, which is especially important in times of limited funding due to a depressed economy and cutbacks in government spending. This research discusses the opportunity for historic preservationists and cultural resource managers to work with land preservationists and natural resource managers in Prince George’s and Anne Arundel counties in Maryland. There are clear ways in which the two fields can come together to work toward shared goals by first realizing the obstacles between disciplines and then creating innovative approaches that connect different programs to protect cultural and natural resources in rural or natural areas. Part of the reason that historic preservation and land preservation often operate independently is because of the long term perception that separates nature and culture. People frequently consider themselves apart from their natural environment, a notion that carries over to the ways in which we manage land and determine land uses. As a result, land managers and historic preservationistis have created different terms, methods and languages for determining resources worth protecting and the significance of an area. The discussion of the human connection to the land is often constructed in simplistic terms as complexity is risky and may require additional time and resources to fully develop.