The formation and development of floral meristems is key to fruit production. However, limited information regarding the development of floral buds during the dormant period of cranberry (Vaccinium macrocarpon) constrains the ability to forecast yield early and accurately. The objectives of this study were to characterize the development of floral meristems from fall to spring and to evaluate the number of floral meristems formed across different bud sizes and upright types, as well as their contribution to the fruit production of the next year. Apical buds of different sizes on vegetative and fruiting uprights were tagged and collected periodically from fall to spring for histological study. An extra set of tagged buds was left in the field to evaluate their flower and fruit production. Five stages of floral development were identified based on the concentric differentiation of organ primordia. Large buds from vegetative uprights developed earlier, had a higher number of floral meristems, and became fruiting uprights; they had the highest number of flowers and fruit. Buds from fruiting uprights had the lowest number of floral meristems and delayed development; subsequently, they had the lowest number of fruit per upright. Our results provide evidence of active floral meristem differentiation during fall and winter, as well as differences in the timing and development stage according to bud size. In addition, our study shows that upright types and bud sizes influence the fruit production of the following year; therefore, they should be considered in cranberry crop forecasting models.