We examined the current composition and structure of a woodland in northeastern Illinois and evaluated the early effect of two prescribed burns. In an effort to increase white oak (Quercus alba L.) regeneration, managers are reintroducing fire into the woodland understory. We assessed canopy species and compared understory vegetation and light, along with soil nutrient characteristics, between a burned and an unburned area. In addition, we monitored transplanted white oak seedlings to better understand their growth and survivorship in the woodland. The canopy was dominated by white oak, but non-oak species, particularly slippery elm (Ulmus rubra Muhl.), ash (Fraxinus spp. L), and black cherry (Prunus serotina Ehrh.), dominated the smaller size classes. There were no differences in woody and herbaceous vegetation, soil, and light characteristics between the burned and unburned area. White oak regeneration was poor which appeared to be due to low understory light levels associated with high density of the shrub prickly ash (Zanthoxylum americanum Mill.) and high numbers of non-oak saplings. Transplanted seedlings also performed poorly, with low survival rates throughout the woodland as a whole. Mammalian herbivory is a likely cause of additional stress to white oak regeneration. Evidence of browsing of transplanted white oak seedlings was apparent throughout the study area. If white oak is to be a component of the future woodland, managers should consider: (1) implementing a more intensive management program aimed at reducing competition from non-oak species and (2) increasing light in the understory.