Climate variability has the ability to impact food production and natural resources. Alabama wheat producers may adjust management practices to reduce climate related risk. The objective of this study was to assess the effect of planting date and relative maturity on winter wheat production in Alabama. The study was conducted in three regions: north Alabama [Tennessee Valley Station], southeast Alabama [Wiregrass Station] and central east Alabama [E.V. Smith Station]. Winter wheat was planted in a split plot design with five replications. Planting dates (four dates) at approximately 15 d intervals were assigned to the main plots and three wheat varieties with early (AGS 2060), medium (AGS 2035) and late maturity (Baldwin) groups were randomized within the subplots. Data collected in 2010 showed that independently of the location, wheat yield decreased as the planting was delayed. There were significant yield differences between locations, planting dates, maturity group, and an interaction between location and maturity. Data also showed that yield can be increased if wheat is planted 15 days earlier than the farmer’s practice. For North Alabama, higher yield was observed by planting a medium maturity wheat variety followed by late maturity. For the central east location, medium and late maturity performed best than early maturity. In south Alabama, yield increase as the level of maturity increased being the late maturity the high-yielding variety. Based on these results, the relative maturity must be selected on a location to location basis and should be considered along with planting date. Crop model simulation using multiple years of data collected from this experiment will be used to conduct simulation analyses to identify optimum planting date and maturity group by different climate scenarios.