Forest tree species in the eastern US such as American chestnut (Castanea dentata (Marsh.) Borkh) and oaks (Quercus spp.) have been negatively impacted by forest changes over the past century. Many mature, introduced pine (Pinus spp.) plantations exist in the Midwest US following establishment 50–60 years ago yet have little economic and ecological value. As oak and chestnut have similar site preferences to pines, these stands may be ideal sites for hardwood restoration plantings. We sought to determine optimal management strategies for converting pine plantations by manipulating their canopies. We underplanted hybrid American chestnut and northern red oak (Quercus rubra L.) seedlings into three canopy treatments (control, shelterwood, clearcut) and included an open field treatment. For each of two growing seasons, 0, 30, or 60 g 19N–6P–12K of controlled-release fertilizer (CRF) were also applied to seedlings. Soil chemical parameters and leaf nutrients were analyzed throughout the study. Chestnut and oak seedlings had significantly greater height after two growing seasons in the clearcut and shelterwood than the control and open field, and chestnut had significantly greater diameter as well. Chestnut height and RCD growth were threefold that of oak after two growing seasons. In general, fertilization increased seedling growth more in the clearcut and open field than shelterwood and control for both species. Soils had significantly higher pH, K, and S in the open field than in pine stands. Results suggest that pine plantations may serve as target sites for restoration of these hardwood species. Shelterwoods and clearcuts are both favorable conversion options for oak and chestnut, and addition of CRF may augment further growth increase, especially in open environments.