Modern vegetable production systems are often characterized by monoculture fields andthe intensive use of tillage and/or synthetic agrochemicals for managing weeds and insect pests. A growing public interest in more sustainable and eco-friendly production practices has resulted in increased demand that crops be produced with lower inputs. Incorporating flowering living mulches and cover crop residues within crop fields can create an environment more hospitable to beneficial organisms and less conducive to pest outbreaks. My dissertation research aims to advance our knowledge in this area by evaluating the impacts of a novel cover cropping tactic which involves combining a perennial flowering living mulch with cover crop residue on insects and/or weeds. Further, it is often suggested that weed management requires a holistic approach; and that cover cropping will not be successful as a sole weed management tactic. As such, another research aim is to investigate whether combining a cover cropping tactic with herbicide sprays would result in better weed suppression and increased yield in sweet corn compared to using cover crops alone. An economic assessment was also performed to further evaluate the practicality of sweet corn producers adopting the management practices being investigated. Cost of seeds, labor and other expenses can be a primary limitation to cover crop usage. To this point, I also evaluated the feasibility of using a single cover crop planting to suppress weeds over multiple cropping systems and field seasons. If a single cover crop planting can be used over multiple seasons, this could reduce the cost of cover crop use. Agricultural intensification and conversion of natural landscapes to crop production fields have contributed to declines in insect biodiversity including natural enemies and pollinators. Advancing our understanding of how increasing vegetational diversity within crop fields influences weed pressure and populations of herbivores and beneficial arthropods, as well as production costs, can facilitate the adoption of practices in annual cropping systems that favor beneficial organisms and conserves insect biodiversity.