Among risk factors associated with reading difficulties, poverty and underdeveloped oral language skills can be particularly detrimental to reading success. The City Early Reading First (CERF) project implemented a comprehensive curriculum, professional development, intensive mentoring, and home supports to enhance children's language, literacy, and cognitive skills. Participants (N = 75) were 4-year-old children and teaching staff from 8 Head Start classrooms in a large urban city in the Midwest. Within the larger project, CERF undertook an intervention - Language Enrichment Group (LEG) - that targeted at-risk preschoolers' oral language development, including vocabulary, discourse skills, and content knowledge. LEGs focused on deepening content knowledge, providing opportunities for language development, and fostering social skills. Whereas nearly half of all 4-year-olds were at risk for later reading difficulty according to fall Peabody Picture Vocabulary Test - III (PPVT) scores, only one fifth remained at risk by spring. Supportive features of LEGs, refinements for future projects, and implications for the field of early education are discussed.