Human development has resulted in significant loss of woodland habitat and its associated biodiversity. Thus, preserving and restoring forest habitats is critical for recovering this biodiversity, as well as the ecosystem services forests provide. While much attention has been devoted to restoring degraded woodlands to their historical conditions, fewer studies have attempted to understand the process of transforming highly-altered, suburban lawn-dominated landscapes into healthy forest ecosystems. In this study, we evaluated different strategies for establishing a temperate forest ecosystem onto land which previously supported managed lawn. Five different native, herbaceous, woodland plants (Arisaema triphyllum, Carex pensylvanica, Diarrhena americana, Geranium maculatum, and Podophyllum peltatum) were planted around five different native woody species (Acer rubrum, Amelanchier arborea, Cercis canadensis, Tsuga canadensis, and Viburnum opulus) in four different leaf mulch soil treatments. We collected survivorship and performance data to assess how trees and soil treatments affected each herbaceous species. We found significant differences in overall survivorship among herbaceous perennials, as well as differences in survivorship depending on species of neighboring tree. Contrastingly, soil treatment did not affect survivorship or performance of herbaceous perennials, although it did influence the prevalence of weedy species.