Of all the factors that can be controlled by farmers, planting date is one of the most important, due to the potential impact on productivity. Planting winter wheat earlier in the fall has the potential to increase wheat yields, and allow for an earlier harvest. This provides an opportunity for an earlier soybean planting date, which should also increase yield. The main objective of this study is to determine whether or not winter wheat in Virginia can be planted earlier than what is currently recommended, to increase double crop yields. This study will allow us to better understand the obstacles growers would face with an earlier planting (i.e. frost damage, hessian fly, lodging). The other objective of this study is to evaluate the suitability of cultivars varying in heading and maturity, vernalization requirements, and photoperiod sensitivity for their potential performance in an earlier planted double cropping system. Certain cultivars will perform better than others, therefore identifying these cultivars is crucial to optimizing an earlier planted double cropping system. This study also provides an opportunity to assess the genetic backgrounds of each cultivar, and whether or not genotypic data can predict a specific cultivar’s likely success in an earlier planting date system. Photoperiod insensitivity and vernalization requirement are controlled by genetic x environmental interactions, and effect developmental stages such as jointing, heading, and harvest dates. Understanding if and how these genotypes affect timing of the transition from vegetative to reproductive stage and ultimately their maturity will allow us to recommend cultivars that are better suited for an earlier planting date. This study includes 4 locations across coastal Virginia and 15 commercially relevant winter wheat cultivars (14 soft red and 1 hard red).