Unlike other rosaceous fruit crops such as apple and cherry, commercial raspberry cultivars are largely self-fertile and can set fruit in the absence of pollinators. However, their floral morphology often prevents complete self-pollaintion. Incomplete pollination yields unmarketable small or crumbly fruits. Insect visitation is therefore essential to maximizing raspberry yield. Honey bees are typically used to pollinate commercial raspberry; however, escalating prices for hive rentals coupled with increasing acreage encourage evaluation of other manageable pollinators. Bumble bees (Bombus spp.) and several mason bees (Osmia spp.) are promising raspberry pollinators. Five bee species were evaluated and compared for their single-visit pollination efficacies on raspberry. From this a pollinator effectiveness index was created and an estimation of the minimum number of visits required to maximize fruit set was calculated. This estimation was then experimentally verified. Finally, in an attempt to synchronize their brief activity period with raspberry bloom, winter management options aimed at delaying the emergence of the mason bee, O. lignaria, were investigated. All five bee species proved excellent pollinators of raspberry. None of the alternative manageable species greatly outperformed honey bees. For this reason honey bees remain the most economical and practical option for open-field raspberry pollination. The adoption of alternative manageable bees could still be justified in other production systems, such as high-tunnel or greenhouse grown raspberry, which hamper honey bees’ ability to forage effectively. The pollinator effectiveness score for honey bees suggested that as few as two visits can achieve maximum fruit set. This estimate was confirmed through experimentation on three different red raspberry cultivars. For two of these cultivars, just one visit yielded drupelet counts similar to openly-pollinated flowers. This information can be used to help refine stocking density estimates for honey bees on raspberry. Wintering bees at 0° or -3° C rather than 4° C effectively delayed emergence of O. lignaria by more than a month without any impact on post-winter performance. These results suggest winter storage at near freezing temperatures is a viable management option for the use of O. lignaria with later-blooming crops.