The use of perennial plant materials as a renewable source of energy may constitute an important opportunity to improve the environmental sustainability of managed land. Currently, the production of energy from agricultural products is primarily in the form of ethanol from corn grain, which used more than 45% of the domestic U.S. corn crop in 2011. Concomitantly, using corn grain to produce ethanol has promoted landscape simplification and homogenization through conversion of Conservation Reserve Program grasslands to annual row crops, and has been implicated in increasing environmental damage, such as increased nitrate leaching into water bodies and increased rates of soil erosion. In contrast, perennial prairie vegetation has the potential to be used as a bioenergy feedstock that produces a substantial amount of biomass as well as numerous ecosystem services. Reincorporating prairies to diversify the landscape of the Midwestern U.S. at strategic locations could provide more habitat for animals, including beneficial insects, and decrease nitrogen, phosphorus, and sediment movement into water bodies. In this dissertation, I present data from two field experiments that examine (1) how managing prairies for bioenergy production affects prairie ecology and agronomic performance and (2) how these prairie systems differ from corn systems managed for bioenergy production. Results of this work show that there are tradeoffs among prairie systems and between corn and prairie systems with respect to the amount of harvested biomass, root production, nutrient export, feedstock characteristics, growing season utilization, and species and functional group diversity. These results emphasize the need for a multifaceted approach to fully evaluate bioenergy feedstock production systems.