The Oriental fruit moth, Grapholita molesta (Busck) (Lepidoptera: Tortricidae) has become a pest of tree fruits since its introduction to the United States in the early twentieth century. Oriental fruit moth has historically been a major pest problem in peach production, and outbreaks in commercial apple (Malus spp.) orchards in the eastern United States were rare until the late 1990s. Recent outbreaks in Mid-Atlantic apple orchards have lead researchers to investigate host-associated effects on oriental fruit moth biology, behavior, and population dynamics. Studies were designed to assess cultivar level effects in apples on oviposition and larval feeding behavior of oriental fruit moth. In a mixed cultivar apple orchard, total oriental fruit moth oviposition and oviposition site preferences varied between cultivars. These preferences also varied over time, when sampling was repeated at various times of the growing season. Although most adult female oriental fruit moth preferentially oviposited in the calyx and stem areas of apple fruit, noticeable numbers of eggs also were laid on the sides of fruit, contradicting some previous reports. Oriental fruit moth females exhibited a strong ovipositional preference for fruit that were previously damaged by oriental fruit moth or codling moth, Cydia pomonella (L.). The majority of newly hatched oriental fruit moth larvae were observed to spend <24 h on the surface of apple fruit before entry, and this behavior was observed on several apple cultivars. Neonate larvae exhibited a preference for entering fruit at either the stem or calyx ends, regardless of their initial site of placement. Our findings underscore the importance of adequate spray coverage and accurate timing of insecticide applications targeting oriental fruit moth.