Springside is a 20-acre park in Poughkeepsie, New York. Commissioned in 1850 by Matthew Vassar, beer brewer and founder of Vassar College, the private estate was both a pleasure ground and gentleman’s farm designed by America’s first and perhaps most influential landscape architect, A. J. Downing, with buildings designed by Downing and Calvert Vaux. Springside is the only extant landscape that can definitively be attributed to Downing, and as such has been a National Historic Landmark since 1969. Subsequent subdividing of Springside has eliminated the farms and orchards of the estate, leaving only the core pleasure ground of curvilinear paths and wooded knolls; all but one of the Downing and Vaux buildings have burned, collapsed, or been demolished. This thesis documents the history of the site, focusing on its period of greatest significance (Vassar’s ownership and residency from 1852-68), and later episodes of alteration and change. It also evaluates the work of Springside Landscape Restoration to maintain and restore the place. Final sections compare management plans for similar historic landscapes and explore alternative approaches to programming as practical, creative choices for preserving the site going forward.